Two week trip for 30th anniversary, a few questions about itinerary

It sounds like a lot of ground to try to cover; every time you shift to a new base you'll lose at least half a day. If you stay somewhere for 2 nights, you'll have just one day there and some hours.

Exactly how many nights will you be able to spend in Italy, not counting the night on the plane going over? "Two weeks" can mean as few as twelve nights.

It will also help us to know your interests. What do you want to do in Italy? Do you want to see a bunch of classical sites? Go inside a lot of museums (often fairly time-consuming), or will you mainly walk around outside, soaking in the atmosphere, and perhaps pop into the occasional church? Are you willing to eat snacks on the run in order squeeze in as much sightseeing as possible, or are you foodies who want to have at least one nice meal per day? Restaurant meals in Italy take some time.

Setting up an efficient sightseeing plan can be complicated by mid-day closures at some sights (between 1 and 4 PM, or perhaps longer in some cases).

The questions acraven has listed are crucial to getting helpful advice. I’ll add some general points that I think apply.

Do you know what an open-jaw flight plan is? This may be more important if you stick to your plan to include Venice and Como.
If you rent a car for the Tuscan countryside, be sure to read up on the multitude of postings about driving in Italy. I don’t intend to discourage you - - - we have done it many times - - - but it is different from driving in the U.S. As they say, “forewarned is forearmed.”
I strongly advise you to take one-day guided walking tours in Rome and Florence. You’ll get efficient overviews of those cities, which are simply packed with important sights.
What is your image of a “villa?” To me, it suggests a very large property, not appropriate for two. Do you know what an agriturismo is? Tuscany is loaded with them, and they can provide a lovely experience.
Keep the questions coming; but, yes, I think your plan is too ambitious. Remember the RS mantra, “less is more.”

Well, I think we will aim for fourteen full days. As for what we want to do, I'd say it's a mix. We want to see some museums, and do some strolling about. We do like to eat, but I don't think we will want to do a big long meal every day. Certainly not in Tuscany, if we rent a villa, we will do some cooking. And other times we might want to just grab pizza or sandwich in a cafe.

I know we want to see the following, but beyond that I can't say for sure.

Vatican City (Sistine Chapel, Vatican Grottoes, St Peter's Basilica, musuems)
Colosseum
Uffizi
Duomo
Galleria Dell'Academia

If we could make it to Venice, we'd want a Gondola ride and see the square, doge's palace etc.

As for Lake Como, I don't think we need to spend the night there, I was thinking we'd fly into Rome and out of Milan. Maybe the day before we fly our or the same day if later in the day we could spend just a half day there and have lunch, he'd probably be happy with that.

Also: What time of year do you plan to take the trip? Weather might affect recommendations.

Looking online the types of places we are considering are small houses in the countryside. 1-3 bedrooms. On VRBO they seem to call categorize them as villas, the ones I have seen. ETA, the category is villa, but in the descriptions they are called farmhouses.

Never heard of an open jaw flight plan, will look into it. We may consider a day tour or two. My husband is an excellent, little fear driver. I'm sure he will be fine, even if my anxiety goes up. We will however stick to driving only in the countryside.

As for when, right now we are mostly considering March/April, avoiding Easter. I don't do heat and the thought of traveling where there isn't reliably used A/C in the late spring/summer, holds zero appeal.

I would not stay in Tuscany and visit Florence from there. Driving and parking always take much more time than you think they will and the areas of Tuscany you will likely be in are probably at least 90 minutes from Florence. Plus, staying in a city and walking everywhere is the best. The things you want to do in Rome took us ½ day each (we usually spent the first half of the day, starting at 8-ish, on a structured thing like touring the Vatican or colosseum, and the second half on rambling a different area of town and going into sites like churches). We were in Rome for 4 ½ days and felt that was adequate to see all that we wanted. We were in Florence for 2 ½. I can imagine 4 days in Rome (full, arriving/flying in the evening of day 0, leaving in the morning of day 5), 3 in Tuscany, 2-3 in Florence, 2-3 Venice, and a stop in Como before going on to Milan for your departing flight the next day. Travel between places will take ½ day (the drive or train may be 90 minutes, but renting the car, departing the hotel or house, returning a car [or getting to the train station, waiting for the train, etc] takes more time than you expect).

Well, if you go in March or April, you definitely won't have to worry about heat; at least not north of Rome. You will want to pack layers to keep warm and waterproof outerwear, since rainy days should be expected. Not the ideal time for Lake Como, I would think. Google the average weather for each of those places for each of those months. Como would have chilly nights with daytime highs in the 50s (F).

Also, I would think visiting Lake Como on your departure day would be a non starter. First you have to get there from wherever you were before, which could take several hours. Then you'd have to get to the Milan airport, which could take 2-3 hours. And you'd have to be at the airport 3 hours before departure. So you'd want at least one night there.

If you want a villa in the Tuscan country then a rental car will be necessary. Make sure you have an IDP for each driver before leaving home. And for heavens sake read up on driving rules in Italy. Speed cameras are everywhere, and speeding tickets will catch up with you several months later at home. The same goes for ZTLs (restricted driving areas) in many cities and towns.

For a first time visitor, I think you would enjoy your trip more if you axed one of your places. As one forum member has memorably said, you're trying to put 5 quarts into a gallon bucket.

I'm currently also doing some advance planning for two weeks in Italy for our 40th, and I pretty quickly came to the conclusion that other posters have stated in their responses. You ain't gonna cover the entire country in two weeks, especially if you want to spend a few days in Tuscany. One member of my novice travel crew-to-be that I'm going to be forced to bring along has seen a few too many movies and wants to "rent a villa in Tuscany for a week" without knowing what that means.

The "simple" mantra people talk about here really does make a ton of sense. I think I'm going to focus on the "must see" stuff (Rome, Florence and hopefully a couple days driving around Tuscany to hit some Hill Towns) for the first trip, and leave the north for another time, even though I'm dying to see the Cinque Terre. Remember, you can always come back for that "villa" stay--it will still be there.

Also keep in mind that return flights to the US do NOT leave at night...they leave morning to early afternoon (although not completely sure of that-based on my travels back from northern Europe countries). This means that, the night before your return, you will need to be relatively close to the airport. This could possibly kill your entire last day if you have to take a long train ride to Rome/Milan/Venice. Oh, and you will be wiped out on arrival day--I always like to take it easy on day 1, and I try to have one "soft" day somewhere in the middle to catch my breath (and lazily soak up the dolce vita with good wine/beer).

Please keep asking questions--I've learned a lot from these forums, and I plan to soak up others' advice as they respond to your questions. Good luck!

Hi,

I agree with ACraven that you could lose half a day each time you travel from city to city. Even if you take high speed trains, the average time from Rome to Florence, and Florence to Venice, and Venice to Milan is anywhere from two to three hours. Add the commute time from the train stations to your hotels, waiting time, check in, etc. and that's, ball parking, three-four hours. If you change cities four times, that's close to 12-16 hours spent on trains instead of eating, relaxing, sight seeing, etc.

Your proposed schedule is ambitious and feasible over 14 nights, but you'll be rushed, and I suspect you'll be left wanting more from each city. When I've engaged in similar itineraries, I've found it frustrating that once I get to know a city, it's outlay, and its characteristics over two days, I then have to leave on the third. My advice would be to take early AM trains as much possible: that way when you arrive at your destination you've got a full day there. Avoid mid-day trains at all costs. As I've written on this blog before, I think you will find Venice to be the most unique city in the world. I know it is packed with tourists, but you're going "off season," so it won't be as crowded as in summer, but it'll still be crowded. There is something absolutely magical about exiting the Santa Lucia train station for the first time and walking down the steps to the Grand Canal. The same goes for taking your first vaporetto ride to your hotel. Whereas the city still has some flooding problems, I always recommend to my friends that they see it before further damage occurs and changes the character of the city. You will not be disappointed: it is absolutely gorgeous and there is no place else in the world like it. And it is easily worth three to four nights, but certainly two nights are better than none.

If you're inclined to skip Venice, you could certainly do four nights each in Rome and Florence and three nights each in Tuscany and Como/Milan area. All three are world class, cosmopolitan cities and you'll never run out of things to do or see. As you've never been overseas before, I suspect you'll be awed by all the charm that Rome and Florence present, and you won't want to leave. The history, architecture, food, museums and culture are amazing. As you're planning on seeing some of the most popular cites like the Uffizi, Vatican, Duomo, etc. I'd be sure to get your tickets as far in advance as you can so you can avoid waiting in line.

One final thought: if your husband isn't adverse to driving, perhaps you could take the train to Chuisi or Sienna, rent a car there, and then sight see/rent a villa in the Tuscan country side. From there you could travel by train north to Florence.
Best of luck, and don't forget to "validate" your train tickets each time you travel.

Here is another suggestion:
1. Fly into Milan- take train from main station to Lake Como - with jet lag stay the night. Based on overnight flight, arrival in Como it would give you a 1/2 day to explore . 1 night
2. Take train into Venice - 2 nights
3. Take fast train from Venice into Florence - 2 nights -
4. Rent car in Florence for Tuscany portion( probably bus to airport to rent one) - you have to be sooo careful of the ZLT zones around Florence - - check out agriturismo's around the area south of Florence, Pienza, Montalcino,
Montepulciano etc. Some of these have kitchen facilities. 5 nights
5. Suggest you drive the car into Orvieto south again towards Rome and leave the car there- take the train into Rome as it is a nightmare trying to return a car into Rome - been there done that.
6. Rome 4 nights

Never heard of an open jaw flight plan, will look into it.

On many/most airline websites it is labeled "multi-city"

Also would it be a good idea to rent a villa in Tuscany and then take the train to see Florence and any other nearby cities from there?

No.

If you want to "take the train to other nearby cities", staying out in the countryside adds the complication and cost of getting to/from the city to get the train to go to the 'other' city. It would be simpler to stay in, e.g. Florence and take the train to Siena , Pisa , Lucca etc from an in town location than to be 'commuting' from the countryside.
A rental car is good for wandering the countryside but a detriment in a town/city.

Doing lunch in some town on Lake Como the day you depart is not feasible. Most flights from Milan that connect to US bound flights leave too early in the day. When flying from Milan, the general advice is to spend the night before in Milan.

Look at the "Itinerary" on the RS tours to see what can be scheduled for a day. Keep in mind the tours move more efficiently due to the guide taking care of all the ticketing and knowing where to go and how to get there. When looking at the transit between cities, the tours have a dedicated bus with door to door service. Your transfers will not be as quick or efficient.

All the villas we have rented in Italy, including Tuscany, had a minimum one week stay, Sat -Sat.
We love Lake Como and have visited there four times. However, your husband’s description is not our experience at all.
Two weeks, Rome, Tuscany with Florence( a stay or day trip) Adding Lake Como is pushing it with only two weeks.

I think Shelley's idea makes sense -- fly into Milan and see Lake Como first, then fly home from Rome That's an example of an open-jaw plan. I loved Venice but if it's the least important to you then I'd say skip it this time. It's well out of your way and, as others have noted, you're trying to see a lot in two weeks. Milan-Como-Florence-rural Tuscany-Rome is plenty, with four of 14 days moving between bases. Florence and Rome have so much to offer, and you definitely want to build in some strolling and cafe and wine time.

I haven't been to Lake Como, but I'd guess it will not be very appealing in March.

The RS guidebook for Italy would be a valuable asset for planning this trip. See if you can borrow a copy from your local library, doesn't matter if it's a few years out of date. Before your actual trip, invest in the latest edition for more current info about hotels, restaurants, hours sights are open, etc.

For more planning /wish list -- take a look at the many free videos on Italy in the "Watch, Read, Listen" section of this website. Unfortunately, they will only add to your list of wonderful destinations.
Two weeks split between Rome and Florence would fit into my admittedly slow travel pace. You could add train day-trips to Siena or Lucca or Orvieto if you felt you had seen enough of the two big cities. (Side note -- Florence is in Tuscany)

Thanks everyone, you give me lots to think about. Sadly I think Venice will have to wait.

So in general is it better to VRBO?Airbnb an apartment/small cottage etc or do you all prefer hotels? We like to rent condos here in the U.S. on vacation rather than hotels, but would like thoughts on doing this in Italy?

My wife and I spent 3 weeks in Italy for our 26th anniversary in summer 2019. The portion of our itinerary that went through ROME-ORVIETO-Rental house in TUSCANY- SIENA (with visit to Florence) might help answer your questions. I posted a trip report on the forum: https://community.ricksteves.com/travel-forum/italy/trip-report-posted-3-weeks-summer-2019-nine-stops-from-sicily-to-milan-with-many-side-visits

Since this is your first trip, obviously you don’t know what you don’t know. Our first trip to Italy, to celebrate our 25th anniversary, was our 4th trip to Europe. We had 3 weeks and started in Rome. Big mistake. Big. I don’t know where you live, but Rome is a big, noisy and chaotic city. I call it NYC on steroids. We spent 3 nights there, then took the train to Orvieto to pick up a car for Tuscany. We spent 4 nights at an agriturismo just outside of Siena (my favorite place I’ve ever stayed), using it as a base for hill towns. We then returned the car at the Florence airport (we didn’t want to worry about the Florence ZTL’s) and spent 2 nights there. We took the train to Lucca and spent one night, then made a quick stop in Pisa on our way to the Cinque Terre for 3 nights. After that we spent 3 nights at Lake Como, 3 nights in Venice and 2 nights in Verona before taking the train to Munich.

My takeaway was that Rome was not as enjoyable as it could have been because we were tired and it was a little overwhelming. Obviously you have less time than we did. I returned to Italy with a friend 6 years later and we flew into Venice. There is no other city like it. We took a shared water taxi from the airport and the approach into Venice was unforgettable. I’ve been to Venice and Lake Como twice each now and I recommend you go to Venice. Lake Como is beautiful, but at the end of the day it’s a lake. Venice is unique. My suggestion is to fly into Venice, where it would be more enjoyable to get over any jet lag. After your stay there take the train to Florence. After Florence rent a car there and stay at an agriturismo in Tuscany to explore the hill towns. Return the car in Orvieto and train to Rome. Rome would be the best place for an apartment IMO. I’ve been to Europe 10 times and the latest flight I’ve taken to fly home was 10:00 a.m. You definitely shouldn’t plan to do anything on your departure day except get to the airport.

We like to rent houses or apartments when we travel, but on this anniversary trip the only apartment we had was in Verona. I think your idea of a Tuscan Villa is probably based on movies, seeing people relaxing by the pool, etc. The reality is that you will be sightseeing all day and in the time you have you will stay busy with that. I would be happy to share my agriturismo information with you if you’re interested.

There are cities in Italy where I prefer to stay in hotels. Venice and Sorrento specifically. Everywhere else I turn to VRBO. Granted, I'll stay a week or two which allows for day trips (especially from Florence, Verona, Rome, Siracusa, Cinque Terre, Lucca, Siena, Assisi). The benefits of a vacation rental, for me, include: washing machine, expanded space, patio/balcony, kitchen and a chance to stay unpacked for a while. The big extras include living more like a local, living among the locals, shopping at the local markets. These neighborhoods are only a block or two away from the 'attractions.' IMHO you get more from VRBO than you get from a hotel (ok, there's no free breakfast) and it can be much more economical.

Lake Como is beautiful. If you need a couple of days of relaxation maybe that's a good place to go. Of course, if you rent a villa outside of a city, you'll be getting the relaxation time there too. Maybe you could relax when you get home?

Since this is your first trip, I might suggest that your itinerary is a bit over-crowded. In two weeks you could Do a quick run through Rome, Florence and Venice - the 3 biggies. Remember, as was said by someone else, each day you change locations is at least a half day lost from your vacation. You could help yourselves out a bit by flying into Rome, train to Florence, train to Venice and fly home from there. Trains are frequent and very fast. Your hotel or VRBO will let you drop off your luggage if your room isn't yet available. Definitely get your guide books out and make lists of 'must sees' in each city. That will help you plan your time but it will also push you to focus on a reasonable schedule for the two of you. You might not be able to see more than 2 or 3 main sites per day. Entry reservations, where available, can help a lot. I always suggest taking a day in each city to just wander around. My rule: if I see a tour group coming my way, I just turn left or right and try to get lost. Funny but those are my best memories of Venice.

Remember, you deserve this trip. And, you can plan your return on the plane home!

I know this isn’t the question you’re asking, but I really think you should consider the Rick Steves 17-day Best of Italy tour. My husband and I first took a RS tour for our 25th anniversary even though we like to be independent. But, we felt like the tour would give us so much more in experience, and we saw that there’s lots of free time. We went on the Best of Italy tour, and my husband thought Venice would be his least favorite of the locations. Instead, it was our favorite! We were able to go to all of the places you listed without any stress - just a great experience to enjoy each day! Since that trip, we have returned several times to Italy on our own, but the tour was the springboard for seeing so much! I wouldn’t hesitate to highly recommend it. There’s a lot of unknowns during that first European experience that the tour would eliminate for you. And if you’re considering driving, do a search on this site for “ZTL”.

Happy anniversary!

Not all apartment rentals allow a visitor to drop off luggage early in the day before check-in time and leave luggage stored after check-out time. Depending on ones schedule, that can be a problem, because the alternative is often to store the luggage at or near the train station. The extra trip to the train station will eat into sightseeing time.

On a short trip involving a lot of moving around, I'd be very careful to choose apartments that use lockboxes for the key pick-up. I prefer hotels myself but have occasionally ended up in an apartment because it was the least expensive option when I searched for lodging only a day or two before arrival. Having to meet up with someone to pick up the key is an opportunity to encounter a significant delay. Of course, if you need in-person instruction on how to use the washing machine, you won't be able to depend solely on a lockbox key transfer, anyway.

Read a lot of reviews about any lodging under consideration. That applies to hotels as well as apartments. I like the reviews on booking.com (which does list some apartments) because you cannot leave a review unless you have stayed at the property.

For a couple making a first trip to Europe involving a lot of relatively short stays, I'd definitely recommend hotels unless there is a real reason to need an apartment. Yes, a Tuscan agriturismo sounds like a good idea since you'll want a car to explore rural Tuscany. Parking would probably be quite costly if you stayed in Florence or Siena, you'd waste time driving in and out of the urban area for the day-trips, and you'd have to be very careful about dodging ZTLs and the like. But during the periods when you're seeing cities, I don't think having a refrigerator and a washing machine is a good trade-off on a first trip for just two people; it nearly always requires giving up a hotel desk where questions can be asked and answered. I'm a highly experienced traveler, but I still often stop by the reception desk and ask what direction I should take to find moderately priced restaurants, or where the nearest market is.

The calculation changes for families, I think: An apartment can provide two sleeping rooms at a lower cost than two hotel rooms, there's a lot more laundry when you're traveling with children, and kitchen facilities save money on restaurant meals and make it easier to cater to picky eaters (if any).

I've driven in France, Germany, Slovenia, Croatia, Austria, and Hungary. There are some reasons to drive. Mostly these are rural sights.

There are just so many posts about SPECIFIC problems with driving in Italy that I am quite reluctant to even consider it.

When we were in France, we visited our friends, where the guy is Chief Engineer of the roads in one of the departments. He said "watch out for those signs about radar speed". I watched out. I got a ticket anyway. It came 2 months after. I got the special "50E extra" convenience fee from the rental company, then had to pay the ticket. It wasn't much, but the extra 75E was annoying. And since we were going to this department which is entirely rural, public transport was not possible.

Note, however, that bus travel in Europe is getting better and better. Flixbus is our favorite. It's not expensive. The busses are very nice. They stop every 3 hours or so for a potty break. You can get a coffee or ice cream or beer. You don't have to worry about drinking and driving.

We have MOSTLY given up driving in Europe. Since we are now in our 70s, it's sometimes not even possible to rent a car. But I doubt we will rent again.

Thanks everyone.

We are definitely planning on using trains, the only time we want a car is if we want to explore the countryside in Tuscany. Otherwise it will be trains or other public transportation for us.

I've considered a tour for the entire trip but it really does not sound like our kind of thing. We are not very social and like to really do things at our own pace and pick where we want to eat etc.

So you all don't think we should rent a small cottage/house etc in Tuscan for just a couple of days to explore with a car? Or just stay in Florence the whole time in a hotel?

Agriturismos are good options for people with cars who want to see the countryside. They are lodgings located on farms, vineyards, etc. Some are quite fancy, offering things like cooking classes. As I believe someone has mentioned, renting a free-standing home for a few days might not be possible; often a rental of at least 7 days is required.

Why not consider the agro-tourismo notion that some have suggested? We did that in Austria. We stayed in a ski-chalet in July. We had the whole place to ourselves. Plus the chickens, ducks, and so forth were very appealing to my children. They were all in their 20s, but still like the animals. However, when you are out in the country, you do need the car.

I've considered a tour for the entire trip but it really does not sound like our kind of thing. We are not very social and like to really do things at our own pace and pick where we want to eat etc.

Had you seen this?
https://www.ricksteves.com/tours/italy/my-way-italy

If nothing else it could be a rough outline to help you plan a DIY trip.

So is there a place to look for agro tourismo places? Would that be different than renting say a small farmhouse/cottage on VRBO?

I do realize some places have minimum stays, that's (one reason) why we will likely go in late March/early April as it seems some are less restrictive then.

That's a great idea to look at the tours as a guide for an itinerary. Thanks.

Booking.com is a very good place to look for lodging of all kinds. Specific to your question about Tuscany, you can put Tuscany in as the location and put in your dates. You can filter the results by many criteria, but the applicable group is Property Type and the applicable choice is Farm Stay which includes agriturismos.

From there you can sort by other criteria. Number of stars is not relevant to much of anything except hotels, so sort by Guest Review Score. Click on Map to see where those results are located.

I highly recommend that you play around with Booking.com for all your lodging decisions. There won't be availability for 2022, but you can look at your potential dates in 2021 to get some hints as to the kinds of lodging and prices. BTW, Villas is also a property type, as are other similar types of places.

Even as a single person, I tend to rent an apartment if my stay is 4 nights or longer. I've also gone through VRBO and Airbnb, but I've had the best experiences with Booking.com.

Note that no matter what kind of lodging you're getting, it's often wise to check prices directly with the provider if possible before booking.

About the driving. Gemut.com is an excellent source for renting a car and driving in Europe. Especially useful is their free, downloadable brochure titled "What You Need to Know About Renting & Driving a Car in Europe": https://www.gemut.com/latest-travel-news/what-you-should-know-about-renting-a-car-in-europe

The current one is for 2020, but they'll update it soon. On the forum some people have said that car rental prices have skyrocketed for 2021, but perhaps they will settle down by 2022. Pay particular attention to anything having to do with Italy. It may be mixed in with other information.

I noticed this link in a paragraph on page 18 about the dreaded ZTLs: https://www.bella-toscana.com/traffic-violations-in-italy/

One more good source, this time for train information is The Man in Seat 61's section on Italy: https://www.seat61.com/train-travel-in-italy.htm

Sort of finally, be sure to take a look at the Travel Tips right here on the RS website for a good place to learn some basics that you need to know about traveling in Europe: https://www.ricksteves.com/travel-tips

And go to the Italy part of Explore Europe for more quick information on the country and various locations within it: https://www.ricksteves.com/europe/italy

Another option to consider is the Rick Steves "My Way" tour of Italy in 13 days. It covers the places you want to go in some form. My Way tours arrange the hotels and bus transportation between the cities. There is a Tour Manager who provides tons of support, but you decide what you do each day and where to eat (breakfast is provided each day.)

My sister and brother-in-law did this as their first trip to Europe and loved it. My brother-in-law is not much of a joiner, but enjoyed the camaraderie of the others when he chose to.

We did the Alps My Way as our first tour after some independent travel, not sure we were tour people. However, the fact that you plan what you want to do and when, but get lots of help from the tour manager, made it a nice balance between knowing people from the group, but being on your own. We had 2 couples who didn't mingle and completely did their own thing. That was fine. The tour manager arranged 1 or 2 Happy Hours that were optional. Also, she arranged optional one pizza dinner and an optional Farewell Dinner. Not everyone went to those events.

You would get a copy of the Risk Steves Italy book as part of your registration. The tour manger was available every morning at, and after breakfast to help people plan their days, if they needed help with anything. Also, on the bus between destinations they come around to check if you need help with planning. Some people had every day pretty well planned, as we did. Others, winged a good part of it, and appreciated the manager's help, but everyone had a great time.

We enjoyed all the added benefits of the tour so much we did 2 more the next year.

If you go to the tour's page: https://www.ricksteves.com/tours/italy/my-way-italy, check out the itinerary, and also read the reviews.

A common thread through all the reviews of the RS tours is "Wow, it was so much more than I expected!"

I'd split a week between Rome and Florence and then spend a week in rural Tuscany. Though I guess your husband has his heart set on Como, which works out okay if you fly out of Milan. You might look at Lago di Bolsena, near the Lazio-Tuscany border. There are some lovely towns in its vicinity. I'd really want a strong contrast to the tourism-intensive cities. If tourism does rebound to half of what it was before, it is important to spread the wealth so to speak.
Every time I plan a trip to Italy, once I start reading about each region I will visit, my trip becomes more concentrated in a smaller geographic region. One, because I hate wasting time moving about, and two because every region has such a wealth of attractions that I'd rather see one area well.

Wow! That's a lot to see in 14 days. One suggestion: we took an overnight train from Venice to Naples (the train stopped in Rome). So we left Venice at midnight and woke up in Naples at 9 am. We didn't lose a day and saved on one night's hotel stay. We had a sleeper compartment and they served continental breakfast in our compartment. I wasn't sure we would get a good night's sleep but we did! One other comment regarding "training". Allow extra time to savor the beauty of Milano's train station if your trip takes you there. It was one of Mussolini's pet projects and it is beautiful.

Since this is your first trip, obviously you don’t know what you don’t
know. Our first trip to Italy, to celebrate our 25th anniversary, was
our 4th trip to Europe. We had 3 weeks and started in Rome. Big
mistake. Big. I don’t know where you live, but Rome is a big, noisy
and chaotic city. I call it NYC on steroids.... My takeaway was that
Rome was not as enjoyable as it could have been because we were tired
and it was a little overwhelming.

I had this exact sentiment first time in Rome, 3 days at the end of a 12 day trip to Sicily & Florence. Yes, we were tired. But you can't tell a book by its cover...

What you want to do is fly into Milan, take the short train to Como, spend 3 nights there. Back on the train, 3.5+ hours to Florence, 4-5 nights there, with daytrips to either Tuscany or Chianti (closer). Then 90 minute train to Rome, and finish off there, 6-7 nights, flying out of Roma Fiumicino. Get an apartment, B&B or nice hotel. Oh, BTW, plan your train travel late morning to early afternoon if possible. Best to get the most out of a travel day, with a good night's sleep & hearty breakfast behind you. Oh, and pack a picnic lunch for the train--so much fun!

Contrary to the reply above, Rome is absolutely world-class, chill, neighborhood-y...with locals walking past 2000-year-old relics all the time. It's positively mind-boggling. March/April is perfect, great weather further south you travel. Few tourists, restaurant/attraction availability. Locals have time to speak Italian or English with you. We spent a week in February 2017, and, once this opens back up again, want to spend an entire winter in Rome. Freedom is the ability to be as busy or as lazy as you want. Enjoy your planning!

People have different travel styles but what has worked for us for decades has been less is more. Two weeks is little time. I would suggest that you rent a place in Tuscany -- we have done this 3 times -- a week near Siena 35 years ago, a week near Lucignano 15 years ago and two weeks in Montepulciano 8 years ago. From there we day tripped around Tuscany which is filled with wonderful towns, abbeys, gardens, hot springs, Etruscan tombs --- Here is some of the scenery from a fall trip we took 8 years ago.
https://janettravels.wordpress.com/2011/09/20/patterns/

I would not commute to Florence -- the memories will be the hassles of getting there not being there. I would choose no more than two other destinations e.g. Spend 3 nights in Venice and 4 in Florence and a week in the country. OR. 4 nights in Rome, 3 in Florence and a week in Tuscany.

It takes two nights to get one full day -- 3 nights gives you 2 full days -- very minimal for a major stop liek Venice or Florence.

It would make sense to start in Tuscany and finish where you will fly home e.g. probably Rome or possibly Florence or Venice. Fly open jaw.

Jay, I was not suggesting that Rome should be skipped. My only point is that it’s a lot at the beginning of a trip when one might be jet lagged. We were there the beginning of September. The timing of the trip would make a big difference.

Jay, I was not suggesting that Rome should be skipped. My only point
is that it’s a lot at the beginning of a trip when one might be jet
lagged. We were there the beginning of September. The timing of the
trip would make a big difference.

I get it, Andrea. And I experienced it that first time in Rome. We were just so weary, and had a list of stuff to see. Saw the Vatican and was pretty much brain-dead. The whole stamina aspect of these trips definitely needs to be analyzed before planning.

Hi. we struggled the first time trying to manage Tuscany and time in Florence. We decided to stay in Florence and spring for a day tour into the Tuscan countryside. We used https://tuscanyexperiencetours.com/ with Andrea Natale. There are a large number of day trips offered. Examples are SIENA AND SAN GIMIGNANO or PISA AND LUCCA. When you get in touch you will learn that he is also entirely willing to put together a day going to exactly and only the places you want to see. For us at that time it was an absolutely perfect solution. He was warm well-informed, and, best of all, he drove and we could just look around without a worry about where we were or how to get to the next place.

Taking into account that this is your first overseas trip, here are my recommendations:

Forgo a rural stay in Tuscany. Driving in Italy is full of pitfalls. Do that on a subsequent trip (no one goes to Italy just once!!) when you've seen what the roads are like and you are familiar with being in Italy in general. From Florence you can take a bus or a train to other Tuscan towns and enjoy the scenery on the way and from the overlooks in those towns. Or you can take a day tour.

Fly into Milan and out of Rome. From the airport go to Lake Como for a night, maybe 2 (if you must :-), then take the train to Venice for 3-4 nights. This puts you in slower paced places for your first few days. Relax, get over jetlag, soak up the atmosphere, get used to the currency, the signs, the language - remember it will mostly all be strange, somewhat confusing, and sometimes overwhelming. You won't need to deal with buses or trams. In Venice it's all walking or taking the vaporetto (water bus) which is easy after the first time.

You can see the main sights in Florence in 2 days, walking everywhere. Stay longer for day trips. End in busy, noisy, bustling Rome. It will be much easier to comprehend the city's major sights on the second week of a trip than on the second day!

Stay in hotels. I can't tell you how much easier it is when you have staff available all the time to answer questions, give directions, recommend sights and restaurants, make reservations (meals, tours, sight tickets). Do you really want to cook (and clean?). You would have to shop for ingredients and most everything in a supermarket is labeled only in Italian. It will eat up a lot of time. That is another experience best left for a return visit.

In Florence visit the Duomo Museum. That‘s where all the treasures are. The actual Baptistry doors blow away the copies on the Baptistry.

We enjoyed Assisi as much or more than the big three.

We like staying in the monastery/convent inns, but they probably wouldn‘t work for an anniversary trip!

Since it's a major anniversary, and since you're not been overseas before, continue doing research and then use a travel agent. Let them sweat the details and planning, that is their job.

Hopefully you have Rick's guidebook, what do you think of his suggested itineraries? Also look at his tours, and see how much ground he attempts to cover in a certain amount of time.

I would not forgo a stay in Tuscany -- driving is not difficult in Italy. we did a week in Tuscany on our first 3 week trip to Italy 35 years ago and have done it since then.

I think the important issue for you is priorities. If your dream is Tuscany then rent a place in Montepulciano or other small town (where you have restaurant access without driving) and spend time in the area --

If Venice and Rome are your dreams then tilt that way. What I would avoid is spending a lot of time on logistics -- a day here and there. Having to constantly pack and check in and out and take trains or buses etc etc is wearing and lessens enjoyment of being there. Figure out what your 3 most important goals are and then build around that.

FWIW on our first trip where we spent time in Venice (5 nights) and visited the Cinque Terre, and rented an apartment near Siena, we also spent a couple of nights in Florence -- and didn't love Florence -- it was all hassles of logistics and little payoff. On your first trip you will find that just the strangeness of everything in a new country to you means things are harder than you will find them once experienced. Little rules about train tickets and bus ticket for example have to be learned to avoid fines. Everything is harder when it is new to you. Basing in fewer places and really spending time enjoying what those place have to offer makes for a nicer trip. We later spend two months in Florence and loved every minute of it and even made some local friends we are still in contact with today. If you want to see what Florence has to offer -- spend at least 4 nights there and get reserved tickets in advance for things like the Uffizi.

all the places you list are good -- but rushing from one to another doesn't make for a joyful and relaxing trip.

With respect the phred, don''t use a travel agent, unless you are sure it is someone who has been to Italy several times! On one of my visits, I had a conversation with 2 women friends traveling together from Australia who were staying at my hotel in Rome. They'd left their itinerary to a travel agent who had made some route terrible plans. Guide books have people who check out their hotel, restaurant and sight recommendations every year or two and they check out many. That's how they make their money. They use local transportation and those people specialize in whatever area they are reporting on. Some (most?) are local tour guides and travel agents.

Back in the day, travel agents were useful. Today, you can find all the information you need on the internet and make your own reservations. Do rely on good guide books and trusted resources like the folks on this forum, with people who've been to Italy in recent years and gone through all the experiences - good, not so good - that await you.

I agree about travel agents. They sell packages -- that might mean using boring chain hotels or local travel arrangements like transport passes etc. They do what is easy, not what is best. With the internet it is far easier for an individual to put together a good plan than to fob it off on someone who may not even have visited that country but turns to their notebooks.

I agree about travel agents. They sell packages -- that might mean
using boring chain hotels or local travel arrangements like transport
passes etc. They do what is easy, not what is best. With the internet
it is far easier for an individual to put together a good plan than to
fob it off on someone who may not even have visited that country but
turns to their notebooks.

Jane is right--it is far easier than it used to be, but the do-it-yourself route is most definitely 'active planning'. You absolutely must be organized, and you have to enjoy planning, which I do. I'm certain it was the same for all of us, but for my first trip to Italy 11 years ago, I was fairly clueless about everything, but soaked it all in like a sponge. For our 2nd (2015) and 3rd (2017) trips, I utilized technology much better and endlessly researched in advance. Excel was my friend, allowing me to manipulate data & dates as plans were tweaked.

Follow-ups with hotels, B&B's and apartment owners were mandatory. Never had to give more than one night's deposit in advance. EMails with them were a little challenging at times, in that English is a second (or third) language for them, but eventually everything got clarified.

It's so much fun--in fact, I'm starting to plan a trip for April 2022, thinking the coast should be clear by that time. And I'm getting that same charge & excitement from the advance planning that I've gotten in the past!

First time overseas in Europe. Hmmm...

I recommend you go see a good travel agent who specializes in Italy if you plan on doing all the places you listed. There are a lot of moving parts to doing what you are planning to do, lots of time lost and understanding how to get around

Those are a lot of places to see spread out from the middle of Italy to the east and to the north. You can do it quite easily but it will be a whirlwind tour of seeing a lot of places but not much depth to what you will see, a very cursory shallow visit which is fine if you want to experience an 'overview' of Italy compared to experiencing Italy by slowing down and digging deeper.

I have no idea why anyone is discouraging you from renting a car and spending days in Tuscany and exploring, a rental car is the perfect way to experience Tuscany as it's country side, walled hill towns, vineyards, the perfect place to do daytrips to all the wonderful towns and wineries, hot springs and history.

Fly into Rome, stay in Rome 3-4 days, rent a car and go to Tuscany Stay in Sienna or Florence and do day trips all over Tuscany for 8-9 days, (Tuscany is huge so many places to experience) (or split up your stay in Tuscany to 3-4 days in South Tuscany and 3-4 in North Tuscany), head north east to Venice (Como is great but will be cold) see Venice for 3-4 days fly out of Venice. That's a fantastic 30th-anniversary trip to remember.

If it is your first time, I would suggest a tour such as one of Rick Steves tours,

Some people love tours but unless you love getting up when someone else wants you to and being at the mercy of the pace of others, and not being able to really immerse yourself in something because we are 'moving along now' then plan your own trips. And odds are high that your own plans will be far better than a travel agents -- they go with canned travel, chain hotels, and tourist products that may cost more than what you easily do on the ground.

With the internet, it is dead easy to plan a trip and seek out places with charm to stay.

I can imagine your husband's attachment to Como -- but you won't be wined and dined by rich locals -- you will be decidedly outsiders looking at a big lake. With so little time is that how you want to spend it? On an early trip to Italy decades ago we spent some time at Lago Maggiore and had a hotel on the Island of the Fishermen with beautiful views of the Alps and the lake -- You might find a resort hotel on Como that would give you some of the feel he is looking for. And of course a boat trip on the lake past those estates he has seen on TV. The Isola Bella on Lago Maggiore was pretty impressive.

If you decide to do Coma -- I would fly into :Milan and out of Rome and would do Como 2 nights, Florence 3, Tuscany 6 and Rome 3. You can probably get an apartment in a small Italian town like Montepulciano for 6 nights rather than a week -- or you might have to rent for a week but you could leave a day early. Better would be Florence 3, Tuscany 7, Rome 4. Quick for Florence and Rome but at least more than just logistics and a week is perfect for the Val d'Orcia.

I just want to thank you all for so much advice. I'm going to definitely be going over it all and considering your thoughts.

I do feel we are not at all tour people, so that's out. But I will keep the rest in mind!

Is it best to ask additional questions in this thread or start a new one?

Is it best to ask additional questions in this thread or start a new
one?

As long as you are still just tweaking this itinerary, I'd stick to this thread. Some like to know the history so to speak when answering questions, and there is a nifty "jump to bottom" feature.

Ok, I've got a little more of a plan, sort of. We plan on sitting down this weekend to figure out for sure what we want to do.

Dh is absolutely set on renting a place in Tuscany for 5-7 days for the second half of the trip. He really wants to drive around and just see what we can see. Maybe hit some small towns and see what they have to check out. As for the rest of the trip I think that's mostly up to me, but he's going to look at the books I have this weekend to see what else might interest him. But I think for him he's mostly interested in Tuscany and good food. I think he may sacrifice Lake Como but we'll see. I would love to spend at least a day in Venice if at all possible (see the Doge's palace, St Mark's Basilica and a gondola ride), but I realize it may not be realistic and we can sacrifice it if absolutely necessary.

For Rome I know I want to see the following:

St Peter’s Square/St Peter’s Basilica
Sistine Chapel
Vatican Museums
Colosseum
Roman Forum
Trevi Fountain
Spanish Steps
Pantheon

For Florence:

Duomo (Florence Cathedral)
The Baptistry of St John
Museo dell'Opera del Duomo
Uffizi Gallery
Accademia Gallery
Pitti Palace

Can we do what we want with three full days in Rome? Or would four be necessary? How about Florence? I was thinking start in Rome, head to Florence and then Tuscany with maybe a day in Venice, then fly out of Milan? Two weeks is an estimate. I imagine with what it looks like this may cost us, another day or two won't make a huge difference.

I think with 3 full days you can do all those things in Florence and possibly Rome. I was in Florence for 3 days and saw everything you listed plus. I won't lie though - it was exhausting. Spread out your art museums though. Maybe Pitti one day, Uffizi one and Academia another. Leave some time for being outside.

I only had 1 day in Rome and managed to see Pantheon, do an underground tour of Collisseum and when through the Forum. Plus it was my travel day from Florence to Rome. It was doable but barely. I walked an average of 8-10 miles each day in Florence and 11 miles in Rome. I'm hoping to go back to Rome in the fall of this year for 9 days to give it the time it deserves. Both places exceeded my expectations.

I want to discourage you from making a one-day trip to Venice. So many people who rush Venice dislike it and say they were glad they only spent one day there. I think that's because if you only have one day in a city that deserves 3 or more, you will inevitably spend all your time at the same sights as thousands of other short-term visitors. The city will seem like a mob scene. If you allow more time (on your next trip to Italy), you will be able to wander the back canals and get lost in one of Europe's most atmospheric spots.

For planning purposes in Rome: The Sistine Chapel is part of the Vatican Museums. It is usually recommended that visitors pay for one of the early-access tours of the museums, because (at least pre-COVID-19) they were nightmarishly crowded otherwise. I think the least expensive early-access option is on the Vatican's website; commercial tours cost more.

I love charming small towns, but when it's your first trip to Italy and there are so many varied options stretching from Venice to Sicily, I think there's some risk the tenth or twelfth cute hill town may be quite a bit less exciting than the first. I don't know what to do about that, because if you've paid for a week-long stay at one place in Tuscany, you'll be stuck where you are. There's a limit to how far away you can go on day-trips. In choosing your Tuscan spot, you might take a look at a map and see what cities/towns might be accessible if you get a bit burned out on hill towns by the end of the week.

I was thinking start in Rome, head to Florence and then Tuscany with
maybe a day in Venice, then fly out of Milan?

Why would you go all the way to Milan just to fly home? Or did you mean that you would visit Lake Como after Venice and then go to Milan for your flight? Because Venice has an international airport, too.

From a logistics point of view, if you want to see Venice it makes the most sense to start there. Connections from the States are good, and it's the most "newbie" friendly place of all the places you've mentioned. As others have previously stated, it is by far the easiest to deal with on arrival with a bad case of jet lag. Then train to Florence, then drive into Tuscany, then train to Rome and fly home from there. The 3 days each for Florence and Rome would be possible, but exhausting. But at least you would have the time in Tuscany to rest up in between.

I think "Venice in a day" (two nights for one full day) would be more workable if you flew in or out of Venice. There is no crime in getting just a peek of a place, but I'd find it annoying to waste time taking the train there and away, whereas if you are flying out of there (as long as it is not one of the super early flights), you get your last day in Venice, and if you arrive there, you start in Venice. That seems like a win-win. That's just more appealing to me when considering travel logistics--I like to minimize moving around.

acraven has good advice about picking your Tuscany region carefully, but there is more variety in Tuscany than it seems at first glance--if you like scenic drives and good food, I think you'll be set in any part of the region. (Of course I am one of those people who finds visiting a farm as rewarding as a world class museum.)
Make sure you have some good regional guides that really get into the nitty gritty so you can balance city-small town-village. My favorite trip to Italy was probably Tuscany's Maremma region. We spent ten days and were mostly outdoors, but if the weather had not cooperated, there were some excellent museums we missed. That area has a lot of Etruscan heritage and a focus on archaeology, which was right up our alley, but it also had plenty of rolling hills with pretty villages and great food. It felt quite different from my previous Tuscan experience of Lucca and Barga, which is up in the Garfagnana mountains and quite different as well. I am basically just tying to reiterate the point to tailor your trip to your passions--not only is Italy so varied, Tuscany is too.

I agree with others who have cautioned you about visiting Venice for a day unless you are flying in and out. Its magical at night and while you can only go so far before you fall in water you will get lost. Its ok and part of what makes it special and everyone who visits Venice should allow themselves the time to wander!

My first trip to Italy was in 2019 and it is a place I longed to visit all my life. I spent 3 nights in Venice, 2 in Varenna, 2 in Sienna, 4 in Florence and 1 overnight in Rome. I was in Germany for a few days before Italy. One thing I wished I'd done differently is slow down and allow time to wander.

Hmmm...I guess I was not yet aware there was an international airport in Venice. I knew about Milan and Rome and even Florence but hadn't yet gotten that far in researching flights. I haven't done much flying and I also thought flights into/out of Rome/Milan would be easier to get and less expensive. I feel like the picking the right flights will be the most difficult thing for me. I love to research trips but have only flown twice in the last twenty years and one of those was booked through a travel agent. I clearly need to learn more especially this part of the trip.

We will definitely be booking museum tickets/tours in advance. And if we can pay more to get a good, less crowded time, will do so.

That might be a long time in Tuscany. But we do like to relax on vacation, especially my husband. He loves to drive and explore and has spent many a day just driving around to see houses, people, animals etc. Even cemeteries, we both love exploring old cemeteries. This is both at home and on vacation.

I enjoy seeing old cemeteries, too. I liked the non-Catholic (aka "Protestant") Cemetery in Rome.

The flights shouldn't be too difficult a challenge. I like Google Flights; others have different preferences. But buy the tickets straight from the airline; that will make your life easier if the airline happens to change the schedule significantly and you need to make an adjustment.

From my origin Rome and Milan are usually a lot cheaper than other Italian gateways, but it might be different for you. One thing to be careful of with Venice is that a lot of the outbound flights with transatlantic connections leave so early in the morning that there's no public transportation available. If you have to arrange a private transfer by motorboat, it will be pricey indeed, on top of possibly needing 4 AM wake-up call. Flying into Venice doesn't usually come with such schedule issues.

A lot of people use this site for flight searches: https://matrix.itasoftware.com/
I always look at the map of airports first to get a sense: https://www.mapsofworld.com/international-airports/europe/italy.html
Be sure to check multi city itineraries.
Nonstop/ to the biggest airports is surprisingly not always necessarily the best. I always check even small airports because 1) I prefer a smaller airport, and 2) you never know when a deal will pop up! You don't want to pay marginally less for a flight to Milan but then have to get there by train (that costs money too) and stay a night there if you didn't really want to.

Another option for flights research is Google Flights.

https://www.google.com/travel/flights

I like its many options for searching, including using the calendar to compare days for round trip flights to see which have the best prices. Scroll down the initial results and click on the "Dates" box to see the calendar with other days near your preferred ones.

Another feature is the ability to set up "Track prices" for flight options and receive an email when prices change. That's under the Dates box for RT flights and pops up when Multi-city flights are chosen.

I use Google Flights only to see what's scheduled, then go separately to the airlines themselves to book. There are links to airlines for the flights chosen, but I've never used them

Fooling around with Google Flights is the best way to learn how to use it, so explore.

As for Venice, I've never flown into or out of it, but the latter isn't advisable because you have to leave so early in the morning. It's not a hub, so you have to fly somewhere else in Europe to get a flight back home.

In general, you have to be at the departure airport 3 hours before your flight back to the States leaves. I've tended to fly into Rome and back home from Milan.

Another thing to think about is jet-lag from your flight to Italy. Don't expect to be particularly bright-eyed and bushy-tailed when you arrive. Just plain bushed is more likely. The challenge will be to stay awake until Italian bedtime. 🙄🥱🙄😴

One more transportation thing. If there's any way you can work it out, take at least one Frecciarossa high-speed train.

https://en.m.wikipedia.org/wiki/Frecciarossa

There's something so cool about looking at the monitor and seeing that you're traveling at 300 km/h.

Enjoy the planning. For many of us, that's a big part of the fun.

The Venice airport is relatively small. With a couple of possible exceptions, there are no transatlantic flights, unlike Rome and MIlan which have many. Departing from Venice usually means a very early flight to connect to a flight from a major European airport. It also could mean leaving for the airport in the middle of the night.

That's why I suggest starting in Venice. It is an easy and pleasant airport for arrivals.

My thought is to simplify and prioritize. What are absolute musts then go from there. Use these points as hubs for daytrips. Staying outside most city centers will require car rental or transit to train stations. If you are considering an agro the hosts may provide some level of transport as well. But keep in mind that this just takes time away from sightseeing by getting from point A to point B to take you to point C.

Have a great trip and Happy Anniversary!

With all due respect, Chani, the op lives in Michigan, so two flights each way is a given. If Venice stays on the itinerary, I agree with those who have said it’s a good place to start the trip - - - small airport, no driving, somewhat relaxing. Meandering its streets is part of the charm, and that can be done any time of day or night while adjusting to time difference.
Florence is a train ride away from Venice. It is deserving of at least 3 days (4 nights), plus possibly a day trip to Siena. A car can be rented upon departure from Florence for exploration of the Tuscan countryside. I still think an agriturismo stay is such a unique and wonderful experience, that first-timers should include it in their plans. Easy to combine with some independent exploration in another part of Tuscany.
After returning the car, (maybe in Orvieto?) a train to Rome could cap off the trip. Trust me, Laurie Ann, you don’t want to drive to Rome even just for dropping a car. There are lots of flights from FCO back to the U.S.

Dh is absolutely set on renting a place in Tuscany for 5-7 days for the second half of the trip. He really wants to drive around and just see what we can see. Maybe hit some small towns and see what they have to check out.

Fantastic.

Tuscany is quite large and can be thought of as Northern Tuscany (Florence) and Southern Tuscany (Siena) If you stay near Florence it gets quite long driving to see the southern parts (Val d'Orcia - this is the calendar shots you see of the Tuscan countryside come from, Montepulciano, Pienza, Montalcino) and if you stay nearer to Siena or further south it gets harder to drive to see the northern parts of Tuscany ( Lucca, Pisa, San Miniato), so consult a map and look at driving times. This is why I would suggest staying in two places in Tuscany if you can, one in the south and one in the north (works well since you are likely heading in one direction on your overall itenary anyways).

Volterra, Colle di Val d'Elsa and San Gimignano are in the middle so you can see them easily from north or south or on the travel day between one stay south and one stay north.

Rosalyn, I was specifically addressing the issue of departing from Venice. Connecting flights would depend on the airlilne, I'm sure there are many choices. Arriving in Venice is certainly an option, but it may complicate including Como in the itinerary as opposed to arriving in Milan.

I'm a little late to the party, and will only address your desire to rent a rural villa, apartment. I did similar some years ago and was very happy with using the train to get into Florence from Montevarchi (closest town/train station). We did do a round trip rental from Florence, but trains were different in 2002. We did have to consider the pedestrian zones, but they too were smaller. The suggestion to pick it up at the airport makes the most sense.
Though part of Tuscany, we stayed in the Valdarno valley area east of the Chianti region. It was less expensive, but well situated for driving to Sienna and the small hill towns south of there....and, the Montevarchi train station. It's a frequent route to Florence, and it was pretty stress free.
If thinking 'Venice', then consider arriving there rather than leaving from there. It seems that many US destination flights leave pretty early and people have the hassle of trying to get to the airport before the regular water transport is running that route. Of course, last night stay in an airport hotel makes that a non issue.

Hi Laurie Ann,

Late to the party but want to mention that since this is your first time overseas and "this is all new to us", I highly recommend reading the following thread:
https://community.ricksteves.com/travel-forum/general-europe/illness-or-injury-traveling-and-on-your-own-or-not

Even tho you're not traveling solo, there's a ton of useful info for anyone traveling abroad for the first time - things like what to pack in a first aid kit etc. Also, one of the perks of staying in a hotel (vs. a villa or Airbnb) is that there's usually someone at the front desk 24/7 who speaks English and can help in an emergency. When 9/11 took place, my DH and I were on Day 2 of our first trip to Italy (12 days total: Florence, Tuscany & Rome; our fifth trip abroad). Thank goodness we were staying at a hotel in Florence - where the staff spoke perfect English, and NOT the rural agriturismo in Tuscany that was next on our itinerary - where no one spoke English and internet access was iffy at best. Thankfully, our hotel manager in Florence was incredibly empathetic and helpful - going so far as to help us cancel our reservation at the agriturismo (he even got our deposit refunded) and helped us find alternative lodging for the next leg of our journey. I'm not trying to scare you, but on your first trip abroad, it's good to remember that this will be a totally new experience and it helps to factor some safety into the equation. There's nothing like an emergency or life-threatening illness to make you glad to have a safety net of some sort, however small.

Having been to both Rome and Venice multiple times, I concur with those who argue that beginning in Venice is better (and far more romantic) that starting in Rome. I love Rome, but it's a jolt to the senses for anyone arriving for the first time; it's crowded, loud, dirty - and remember, if you start there, you'll have to deal with all of that while jet lagged. Not fun. Meanwhile, Venice is magical. There are NO CARS! You'll be walking or riding vaporettos (water buses, but so much better than a traditional bus). It's so different compared to SE Michigan - that right there is half the beauty. You mentioned your DH likes stopping to explore cemeteries; Imagine seeing a casket being taken to a cemetery (that's on a separate island) via a water taxi? We've seen it. It boggles the mind. The canals and lagoon are incredibly beautiful. It won't be crowded or hot in the spring so you're timing is good. And I totally agree with the person who said that there's nothing like arriving at Santa Lucia Train Station and catching your first glimpse of the Grand Canal. Few things can hold a candle to riding a vaporetto or water taxi to your hotel. Venice is truly magical - 3 night minimum IMHO. I could ride the vaporettos all day or evening long (great for anyone jet lagged) - visit the outer islands like Burano, wander the streets in the Dorsoduro neighborhood, wake up early to see the sun rise and have St. Mark's Square all to yourself. It's truly lovely. Trains between Venice and Florence are easy-peasy, and from there, the high speed train to Rome. Just my 2 cents.

If you insist on going to Tuscany, consider staying in a hill town like Siena, rather than a villa in the countryside (and yes, most do require a Sat to Sat stay).

Finally, having grown up in SE Michigan, I can honestly say that driving in Italy is much, much different that driving in the Midwest. We've done it multiple times, but it can be incredibly stressful. Traveling via train is far more relaxing and less expensive - it's what we do more often than not. And don't forget, if you drive to a restaurant, forget having wine with your dinner if you have to drive back to your villa. Don't do it. It's illegal and dangerous. Staying in a city like Venice, Milan, Florence, Rome, Orvieto or Siena means you be able to walk "home" from dinner - don't underestimate that convenience when planning your trip.

Just saying, if we are going to a country to travel around for the first time, our accommodations are usually hotels. I think there is great and not-to-be-ignored value in
having people at the front desk who can answer your questions (Is there a great cigar store here?) or make suggestions. In Samaur, which was simply a place to break the drive to Rouen, the hotelier said "But of course you should cross the river and visit le Cadre Noir". He not only gave us tickets, but called and spoke with a friend who met us when we arrived and gave us a 90 minute tour in English of the facilities, the horses and the riders. Later visits we may do otherwise, but first time we are deeply grateful for great advice available at the desk.

Just saying, if we are going to a country to travel around for the
first time, our accommodations are usually hotels.

Yeah, I'm in agreement with Kate. First trip in 2010 to Sicily/Florence/Rome, it was hotels. Fine & dandy, everything taken care of for us while we got the lay of the land. 2015, we dipped our feet in the water by renting an apartment in Florence for 5 nights. Went fine, although the owner was wonderful and made it easy for us. In fact, we'll be staying there next April (2022).

In Rome, we kinda got the best of both worlds. We had stayed at a hotel on Campo de' Fiori in 2010, and for a return in 2017, they had bought up some of the 'residenzas' on the perimeter of the piazza, and we grabbed one of those for a week. Very small, but if we had a problem--never really did--the hotel was just across the square. Dirt cheap too, at about $85/night.

My point is that you never know renting apartments--or B&B's for that matter--if you're going to get a pig in a poke. Pictures on websites can be dolled up to look like just about anything. We had that experience at a B&B in Sorrento--we made it work but we were overall disappointed. You just never know.

I think experience & research are key. Our first apartment in Florence, I was very diligent in searching out reviews, then I was probably a little over the top in advance EMail communication with the owner, but I felt that even with a written language barrier, I could maybe tell whether they were legit. I could tell, and she was.

So...for the first trip..in renting places, it just appears that there are many more things that can go wrong than go right. What did travel writer William Least Heat Moon say? 'Be careful of wishing for adventure while on the road. More than you bargained for is ridiculously easy to find'.

That being said, for any length of 5 days or more in one location now, we will try to find a reasonably-priced apartment, preferably one we've stayed at before or by personal recommendation. It's fantastic to really get a feel for a place--for us Florence & Rome--by having your own abode. Good luck!

Hi there, Laurie Ann. I'm late to the party here too but a couple of comments?

Renting city apartments versus booking hotels: I'll always vote for first-timers abroad to go with hotels. There are enough learning curves to getting acclimated in a foreign country to begin with that 24/7 desk service can be reassuring, especially if some unexpected event - say a medical emergency - makes having help at hand well worth the choice. Prior to COVID, a great many hotels also included breakfast of some sort or another in the tariffs; another plus in our book. Once acclimated to how Italy 'works" and/or are comfortable that you could handle a fairly large problem by yourself, then apartments can make sense, as in our Jay's case. As someone already said, do you really want to spend time shopping, cooking and washing dishes?

Jay can laugh as he knows that I am only marginally acquainted with my own kitchen. HA!

Speaking of medical stuff, make sure to check your policy to see what it covers, or not, out of the country. Many of us buy at least medivac insurance should we need to be airlifted back to the U.S with support as that is REALLY expensive.

As well - as this is definitely NOT a criticism as it's easy to be seduced by gorgeous photos!!! - I'm sensing that you two could benefit from choices that will make acclimation easier and your trip more enjoyable. You DO have plenty of time yet for lots of research but, well, just your DH's perception that Lake Como will be populated with lots of wealthy people "having fun" .... I'm with some of the others who wouldn't personally choose that area to visit in March; a lot of restaurants, hotels and whatnot there will still be closed for winter.

We've done Rome right off the plane without any issues but I'll agree that it's definitely not a city to be rushed. Yes, it's busy but the historic center isn't all THAT vast, and there are interesting corners for finding breathing room IF you give it enough time to wander away from the most-visited attractions. Florence's historic center is pretty compact but packs a punch; LOTS to see. We've personally no interest in rural stays as we enjoy the sorts of attractions cities and towns offer, aren't interested in amenities such as pools, cooking classes, on-site restaurants, spas, livestock, etc. and like having public transit close at hand for flexibility. Still, I do understand that they appeal to a lot of folks, and it's your trip so go for it if that's your thing. Still, heed the great advice to read up on the rules and regs of driving in Italy, and understand that you won't be wheeling right into some of those small Tuscan towns that have restricted driving/parking zones.

Airports: yes, Venice has an international airport. While Milan has several airports, the main one for most long-haul flights is quite some distance outside of the city, technically in Malpensa, about an hour outside of central Milan. One note about Venice (Marco Polo) is that flights to the U.S. do tend to leave early in the morning and that can create some interesting/expensive challenges getting there via public transit depending on where your accommodation is. The advice is usually to fly IN to that one and out of Rome (Fiumicino) if those both cities are on the itinerary.

If cutting Como and Venice, you could look at little Pisa International (Galileo Galilei) to access Tuscany.

We've personally no interest in rural stays as we enjoy the sorts of
attractions cities and towns offer...

Again, personal preference but I'm with Kathy. As she says, the cities allow the flexibility of doing something..or 'il dolce far niente', loosely translated as '...the joy of doing nothing.' You would think it's the other way around, right? Not really. I'll give you Rome--my favorite place in the universe--as an example. Certainly if you're situated on one of the main drags, like Vittorio Emmanuele or near Termini station, it can be pretty frenetic. But for the most part, Rome consists of a lot of small neighborhoods, usually around a central, ancient piazza. Which is perfect for escaping with a fizzy aperatif in the late afternoon at a tiny outdoor cafe where you can sleepily regroup and watch the world go by. Have done it many times!

For our last trip there, we had lists of stuff we wanted to do, places we wanted to see, restaurants we wanted to dine at, all compiled from advance research. Not in a daily itinerary, like (God forbid) a tour, but simply a list. Each morning, we'd laze in our apartment, windows open while the market vendors were setting up their wares for the day. We'd drink coffee, eat fruit and prosciutto, and while looking at our street map and laminated bus & Metro routes (we got our weekly passes for 24 Euro on day of arrival), decide what route to attractions made sense for the day, depending on the weather and frankly our energy level. After awhile, we'd venture out and be gone for a few hours, coming back to nap, shower and then have a leisurely 3-hour dinner at a local trattoria within walking distance, then of course gelato as our nightcap. It was heavenly.

In a rural area--granted, it's quiet, serene, but most often you'll need a car to go anywhere. And beyond the agriturismo or farmhouse or tiny village...that's it, baby. Even though you're in the open spaces, you're a captive audience.

Different strokes, y'all, but this is what floats my boat about Italy.

To add to all the excellent advice -- "hotel" doesn't have to mean a sterile Hilton. Many small family-run hotels all over Italy (check out the ones in Rick's books) have the advantages mentioned but have the charm of a villa.

I'm really torn on what advice to give you, especially since you've not been to Europe before. Do you travel much in the states? Are you good at planning all the details?

On one hand, I'm tempted to agree with those who suggest taking a Rick Steves tour. It would be a great reconnaissance tour, allowing you to get your feet wet for taking an independent trip for your 35 anniversary. RS tours are small and I think you could choose how much interaction beyond the necessary you'd have with your fellow travelers.

On the other hand, the internet has made it really easy to research and reserve your trip. If you are willing, you could handle everything yourself.

Do you like cities or the countryside? Your choices will be governed by that. On our last trip to Italy, we decided to really slow down the pace. Since we had been to Rome, Florence and Venice before, we decided to spend our time in Tuscany. We rented an agriturismo and explored the countryside from Siena in the south to Volterra in the north. We rented and drove to anywhere we could reach in an hour or so or less. We did scoot in to Florence for a day, taking the very early commuter bus that dropped us off in the heart of the town. We also spent a little time in Rome before heading home. There's an entirely different side of Italy when you leave the big cities.

You can't see it all in two weeks. If you try, you'll end up seeing nothing. It will all be a blur.