Questions for Early Stages of Planning 2 week Trip

I don't think you will find any lesser crowds in Rome-Florence-Venice. Perhaps in the coastal places in October.
Start searching "multi-city" (aka open jaw) flights now, and buy when you see a schedule and price you can live with. I typically buy 3-6 months out.
I fairly quickly determine where I want to go so I can get my accommodations of choice. It's never too early.
I don't think I would necessarily visit Cinque Terre AND the Amalfi coast, even if you had the time. Of course there are many differences, but basically both are pretty seaside locations and I consider both in one trip redundant. CT is extremely crowded, and there is very little to do in inclement weather. I found it easier to escape the crowds on the AC, as the area is larger and more spread out.
So, for now I would concentrate on your own personal must list. There is no rule you must see all of the big three on your first trip.
Note that rural Tuscany is best visited with a car, which some find intimidating for a first trip, so decide what is in your comfort zone.
Start making lists of what you want to see and do in each place. It is okay for example, to just stop over in Florence for a day just to see one thing and get your rental car--though some will call it a travesty.

I don't know where you are from but if you include travel to Venice, I'd fly in there and not try to fly home from there. To me, the Venice airport is a hassle to get to (all that water, you know?) plus not many (if any) non-stop flights to the US. If you try to depart from there you may be presented with the option to have a really early AM flight from there to a European airport hub where you can get your flight home. With the limited time you'll have you won't want to use the strategy of flying to the hub the day before (or spending a few days there) your international flight back home. Getting to the Venice airport for a 6A flight is a pain in the neck.

I'd probably try to fly in to Venice and out of Rome.

I'd also agree you might need to edit your list. Amalfi Coast is the outlier in your list and really, you'd probably not want to do 2 coastal areas.

Personally, I have found four locations offer a good balance between variety and ease. When you can, open jaw airfares make life much simpler if you are traveling a long distance.

The amalfi coast cannot easily be combined with Venice. However, I think it could be combined with Florence and Rome (but then not cinque terre). You could fly to Rome, immediately take train to Florence, then train to Salerno and make way down the coast, and then return to Rome at end.

Or fly into Venice, then to Florence, cinque terre and Rome. Fly out of Rome.

Or skip cinque terre and do a few day trips to small towns (like sienna near Florence).

I would start looking at airfares for this fall now-just to get an idea of routes and prices. I seem to see best prices out 9-11 months but have never been prepared to pounce but perhaps you could be.

Beth

I think last week of September/first week of October is perfect, we went during that time 3 years ago and still got some decent daylight at night and perfect weather.
You can't spot a "good" airfare unless you have a starting point. What I would do is start an excel spreadsheet with todays airfares (since this is the time your wanting to go) then just check in once a month or whatever to see how it fluctuates, then you will know a deal when you see it.
We are also in our 50's and like a fast, slow, fast pace. So Big city (Rome), small city (Cinque Terre). If you want to see Tuscany I would base in Florence and from there you can do day trips, or a couple nights in Florence and your close to other Tuscan cities to travel to for longer periods.
With 12 days (total or does that include your flight days?) You could do Rome (3), Florence (4) and Cinque Terre (2- that is all you need IMHO) and Venice (3) or skip Venice and do the Amalfi Coast (3) base in Sorrento. Look on a map for the best order so you don't backtrack and the last place should have a airport you can depart from.
Rome-Florence-Cinque Terre-Venice-Sorrento are all served by trains, which makes them easy to get to, no car needed.

Beth has some good suggestions on focusing your trip with Rome/Florence/Amalfi Coast or Venice/Florence/Rome/CT, it is difficult with your timeframe to squeeze in both Amalfi Coast and Cinque Terre.

A couple of other things to think about in your planning since this is your first time to Italy (not sure if it is your first time to Europe as well).

• Rule of thumb is every time you change a location, you lose half day in transit (packing, checking out, transportation, checking in), so factor that in planning the number of cities that you will be visiting.
• Day of arrival is usually a lost day unless you sleep well on a plane. You may be able to do some light activities, but don't expect to power through a major museum on the day you land. Day of departure is usually a lost day as well, so factor your planning based on the actual "real days/nights you have for seeing the sites.
• Moving around a lot is not a vacation or relaxing in the US and it is even more challenging in a foreign country. If you want to relax, staying at a location as a base and then taking day trips, is an option.
• To see Tuscany the way you want to see it really needs a car. The good news is that driving in Tuscany is straightforward (just know the traffic laws and have a good GPS). However, driving in a foreign country can be stressful. For us, it wasn't the driving, but finding a parking space big enough for the minivan with 6 people.
• Get the RS Italy planning map (or download a map), then plot out all the locations you want to go to, travel options (train/car) + time & cost. For my group, this was the only way we could narrow down the choices. For example, we ruled out Pompeii after we factored in the travel time.
• Booking: Google flights gives great options. Also, check your airline if you have points. For my late May trip, I flew 4 people on miles for 240,000 miles all in economy plus on United. I found that over New Year's Day brunch with friends. For accommodations, I waited until March and I had a very difficult time getting hotels for 6 people, especially in the Cinque Terre and Venice (RS travelers and tours book a lot of his recommended spots). If I had known, I would have started looking earlier. That said, I found great places to stay (rentals and hotels), but it was a lot of extra effort.

Have a great trip.
Sandy

We were in a similar planning mode in 2017. Mid 50s, first time to Italy, mix of locations on our list. We decided that Venice and Amalfi were outliers for this trip (although we did them both on the next trip in 2018).

This worked well for us:
3 nights Rome
3 nights Florence
3 nights Vernazza CT
3 nights Montepulciano Tuscany
1 final night Rome

We trained everywhere, except Tuscany where we picked up and dropped off car in Chiusi.
Direct flights from and to Newark NJ.
Italy is great, you are gonna love it!!!!

I'll just address the flight question.

I don't know where you live, so I don't know whether you're looking at lots of reasonably priced options with a goal of catching an especially good deal or are at risk of having to pay over $1500 apiece (to get out of a tough spot like Montana) and just want to avoid a disastrously expensive fare.

My practice is to start looking at fares and documenting them as soon as I have a reasonably firm idea of my destination and travel dates. I live in a fairly competitive market. I keep looking and recording until I see a healthy drop in the fare or become convinced that it's not likely to happen. You never know what will happen the next day, but you're in a better position to make a rational decision if you have information about what fares have been doing. I try to remember to check fares every day, because there are definitely cases when a fare drops for only 24 hours (or even less). It's easy to miss those short-term blips. Websites like Google Flights allow you to set up a fare alert for a particular itinerary; they'll send you emails when the fare changes. I use that tool but don't like to depend on it totally, so I continue to do my own checking.

When you first begin your fare research, that's a good time to fiddle around with departure and return dates to see whether shifting your schedule forward or backward by a day or two might save you money. Those patterns can shift over time, so things might change before you decide to click the "Buy" button, but often the day-to-day variation is pretty stable, so it's useful to know what day(s) of the week may be cheapest for you to fly. Similarly, if you have the option of flying out of multiple airports, check all of them initially, discarding only those that are very clearly non-competitive for flights to Italy.

Finally, consider running your trip in whichever direction will give you the cheapest airfare and decent schedules. If you were traveling after mid-October, I'd suggest starting in the north (due to weather), but if you go earlier than that I think it probably won't matter too much.

Time is money. Don't get too entranced by a deal that saves a few hundred dollars but gives you the opportunity to experience an airport in Moscow or Istanbul on the way to Italy. When you have to change planes along the way, that's a whole 'nother story. Not all flight connections are created equal. I'm willing to pay extra to have 2 hours for the connection rather than just 1 hour.

Thank you so much, everyone! This helps very much. You have given me direction on many of the items I needed in order to get started.

As far as flights and travelling, we will most likely fly from Chicago. When I did a quickie search a few days ago I saw flights from Chicago to London to Rome for about $1100 each. Good idea to start tracking it. I was actually surprised to see that flights could even be purchased this far ahead.

Most of you recommend picking one coastal area, makes sense. I definitely do not want to over extend ourselves.

As far as booking accommodations I know I need to read my book, but generally how far out do I book these? I have read discussions of people staying in apartments, hotels, rooms, etc. We would like off the beaten path, but nice, accommodations that will enrich our experience. Someone mentioned using RS recommendations, which I will try to do...any other suggestions or advice on this?

Thank you so much for the help.

Hi Laurie, I read your posting, and this comment stuck out : “We need vacations to be a slower pace than life, so big cities hustle/bustle does not appeal to us generally.”

I’m glad you are planning ahead, so you have time to consider so many options for a trip to Italy. Instead of a R/F/V itinerary, you might rather have an itinerary that’s flying into Milan and heading to Cinque Terre or relaxing at Lake Como and then heading to charming Siena in Tuscany followed by an agriturismo near Montepulciano to enjoy the Tuscan wine region. You could either fly home from Rome or Florence.

Another option would be to begin in Venice, then head to Verona and then down towards Tuscany and fly out of Pisa after being at Cinque Terre and possibly Lucca.

You don’t necessarily need to hit The Big 3; there’s so many wonderful towns which keep bringing me back to visit! (Also, maybe check out the Rick Steves Village Italy tour itinerary for either ideas or possibly to join it.)

Regarding accommodations: Once you have outlined your itinerary, use booking.com or another similar website to get ideas of locations and availability. Generally, you won't want to book accommodations until you have purchased tickets for your flights--but if you find a property that you just HAVE to stay at and don't want to risk it filling up, be sure the reservation can be cancelled if you end up with different flight dates! Also, research each place where you would like to visit for special events such as trade fairs, local festivals, etc. These can cause dramatic changes in price and availability--but you have plenty of time to work with your dates so you can either take in or avoid these high demand times. In my experience, I prefer booking directly with the property. Do a Google search for the website; if the property does not have a website (some small ones do not!), email them directly. We usually receive replies within 24 hours. Once in Italy, be sure to connect with the staff at the front desk, host at a B & B, etc.--they are a wealth of information and can help you have some marvelous off-the-beaten-path experiences.

I see this is your first trip to Europe--congratulations! A great resources for European travel in general "Rick Steves Europe Through the Back Door". For train travel, the website seat61.com both tells AND shows you how to travel by train.

We, like you, prefer travel that reflects "a slower pace than life". You've received great itinerary advice from others that will help you plan this trip and truly enjoy Italy. (And, you'll have a long list of "next time" places to visit:)!) Enjoy the planning--and happy travels!

Again, more great info from you kind, experienced travelers! Helps to hear the order and timing of making reservations. I did get on booking.com last night and see many choices for inns/hotels/apartments. And I put the Europe Through the Back Door book on hold from the library. I am so glad we are starting this far ahead so that we can do this the right way! And, yes, we definitely want some time to sit and relax with a bottle of wine and take in the environment.

Not sure if you can answer this because so many factors.....aside from airfare, what would you throw out there as a ballpark range of budget for a 2 week trip like this? We are value minded but I would say we will spend moderately, not elaborately. One of the books ballparked at $175 per day per person, not including airfares. Does this seem relatively close to your experiences?

Thanks!

Just wanted to share this agriturismo since you mentioned a desire to stay at one. I believe it is listed in RS book, gets great reviews, just outside Siena. I think it would book up quickly.

http://www.agriturismomarciano.it
We did not stay here but almost did- decided to spend our time visiting/overnighting in diff 3 hill towns instead.

Our first trip to Italy (but not first to Europe) was 17 nights Sept 2014-
we did
Venice 3- direct flight from PHL
train to Florence 3 nights
picked up car outside the ZTL
Siena 2 nights
Montepulciano 2 nights
Assisi 2 nights
dropped car in Spoleto and trained to Rome
Rome 5 nights- direct flight to PHL

We felt it was perfect and I got so much great advice here on this forum.
We absolutely loved every town and city we visited and are going back May 2019 for more.

Be sure to get the RS Italy book - we used that along with the RS books specific to Venice, Florence, Tuscany & Rome.

Laurie, per your question about a ballpark figure for cost, here’s what we spent on an Italy/France trip in 2016 per day average for us traveling as a couple, I.e. the hotel average is $76 ea. X 2, so $152 per night. The larger cities or more touristy locations cost more than the smaller towns.

Hotels: $76 each
Meals: $33 ea. (we eat lighter for lunch, and breakfast comes with the hotel). Wine would be extra.
Transportation: $18 ea. (Travel by train)
Activities: $20 ea.

That’s $146 pp, so your initial budget of $175 would be fine.

Jean has a modest budget and I salute her! We travel with a bit higher budget.

Our last two trips we were more in the $150/night range and $90-95 for food and beverage. We rent apartments and cook some, but when we stay in hotels we tend to pay a little less on lodging but more on food and beverage. We only splurge on a few meals (i.e., maybe once a week a dinner will be $90-100). That said, I would only rent an apartment in a location for 4 or more nights as there is so much benefit to having a hotel or B&B staff at your disposal for shorter stays. You don't want to have to figure everything out for yourselves.

Transportation is hard to estimate broadly, but as you get into planning, you can easily look up the cost of a train between major locations (get familiar with www.Trainline.EU) and see what discounts are available. Ditto if you rent a car for a few days you can get a quote but note fuel is expensive, there are tolls, and insuring a rental car in Italy is costly.

Entrance fees, tickets, passes, and tour fees can be easily researched. Rick lists them in his guides and I like to double check them online as they always seem to go up a Euro or two each year. Add in a bit for laundry. Not uncommon to spend $15-20 to do that and we were so surprised by that on our first trip in 2010!

I do a spreadsheet with everything I think we want to do and start filling in prices. My estimate for food is always $100 per day even though we usually underrun that (except in Switzerland and London!).

FYI, I used dollars on purpose as I converted our latest trip (Sept & Oct) just yesterday. Over the years (2010-2018) our food cost per day has stayed amazingly constant but lodging has gone up. I think that is because we are a little more particular on our lodgings these days. An elevator is a must for us if the room is above (European) first floor as we hate hauling the luggage up more than one flight. OTOH we never rent cars anymore. Public trans in Europe is so good and such a bargain.

Thanks for the heads up on the expenses and ideas on how to estimate. Looks like we have a starting point on what to expect now. Laurel, are you saying there will be less help and assistance if we stay in apartments? I think we do want the “quaintness” of mixing with the owners and other guests. Good to know. Thanks everyone again.

The biggest advantage of hotels is being able to leave your luggage there upon arrival and sightsee if your room is not available yet. We find this to be hugely helpful. If you need early morning transportation to the airport, the hotel can arrange it for you and the transportation may be more reliable since they want the hotel to continue to call them. You can also get ice from the bar if you need it-not just for drinks but for injuries or sore muscles.

Yes, with apartments you get less help. Sometimes the owner is next door or down the hall, but you’d be knocking on the door to get help. Many apartments are quite hands off. We have been given keys and codes to let ourselves in and never seen the owner in a week long stay.

Meant to add, a B&B is a nice situation for mixing it up.

cala and Laurel have given you good advice. We stayed in a hotel in Milan, and our friends in a rented apartment. They had limited (and difficult) communication with the owner. Lots of questions they couldn't get answered. It ended up okay, but just not a pleasant experience and this was not their first trip to Italy (or Europe).

Our hotel, on the other hand from extremely helpful, arranged morning transportation to Linate (on time and price was what they quoted), and a very good breakfast. We were only there 2 nights, so for us, a hotel made more sense.

You've gotten lots of great advice.

I'll just comment on your choice of destinations in Italy. You're right, many first trips are structured from Venice to Florence to Rome with various diversions along the way. Rick even has a VFR tour, as do many other companies. That's for two reasons; it's easy to travel in a line, and those three cities are not only highlights of Italy for many, but have lots of the "brand name" sights that first timers want to see (the places they've heard of, that others will ask if they've seen).

However, as you say, you can indeed just use big cities for their airports, and spend as little time in the cities themselves as you want, focusing instead on other places. You do want to be close to your departure airport the night before, but even this doesn't necessarily mean being in the city itself. For instance, you can stay in the Lago Maggiore area and still be be in easy striking distance of Milan Malpensa airport, or take a bus directly from Padova to Venice airport.

So, if you really want a more small town and rural trip, you can have it. But there's something else to consider. The longer you spend in a big city, the less of a hustle/bustle the visit becomes. You can spread your sights out over more days, so you're not running around as much. You get to know your local bar (what we would call a cafe) and other stores, so you feel more "rooted" and less transient. You get to learn your way around, so you're not always looking at a map. (No, you're not a "temporary local," but you are at least not just dashing in and out). And you have down time to do things besides just sightseeing - you can wander a quiet neighborhood or spend some time in a park. On the other hand, if you have only two days in Rome or Venice or Florence, often much of that time is spent running from sight to sight - creating exactly the hustle/bustle you don't want. People who only have two days in Rome find it much more stressful than people who have four days.

In summary, make this YOUR trip - not someone else's. If you only want to spend a small amount of time in a big city, do so; just make sure that if you are going to a city, you don't create the fast pace you're trying to avoid.

Harold has explained that very well. Trips that spend too little time in Famous City A, followed by too little time in Famous City B, etc., are going to feel very hectic. You don't have to travel that way.

One thing to check if using trains, busses, etc. weekends and holidays have a different schedule. I would not plan to travel on holidays or day before or after on trains. Italians love to go on "strike" the days around a holiday...more time off for them....but, a hassle for you! Otherwise we have had no problem with public transit. Don't buy train tickets here...buy at a kiosk in Italy. Trains are super cheap and there are many more options available than you will see here. Second class is fine also. But, do remember to stamp...validate...your ticket before getting on train...we did not know that on our first trip and it cost us a huge fine!

Waiting until you get to Italy to buy tickets for long-distance trains can double your cost or more. That can make sense; maybe you're not certain about your itinerary or your timing. But if you do have your plans locked down, there's money to be saved by buying the long-distance Freccia tickets ahead of time. Just understand that the cheapest tickets are non-refundable and non-changeable.