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Itinerary help for Italy first timer - 15y Anniversary Trip

Hello all -
I am taking my wife for a 15 year anniversary trip in early June 2019. I love travel, my wife needs more convincing. I want to make this trip special so I'm designing it around her preferences. Some info:

  • 7 nights maximum (need to get back for the kids)
  • My wife is not a backpacker - meaning, she doesn't want to pick up and stay in 3-4 places over 7 days. I think 2 places over 7 days is the max.
  • My wife likes small/quaint/cute towns over cities. I think she would really enjoy the small/medium Tuscan towns. So, because of this I was planning to base out of Florence/Tuscany for the majority of the trip.
  • I will be getting a rental car for at least the Florence/Tuscany portion, likely the whole trip if it works best.
  • I expect to come back to Italy in 2-4 years with my family, so we do not need to see everything. If we miss Rome, we can catch it next time.
  • This is an anniversary trip as I said above, so I want to plan accordingly (romantic and couples related stuff)

With all the above information, how would you design a trip? My plan was to spend about 5 nights in an agriturismo just outside of Florence (maybe max 30-50 minutes). During the days we would spend 2 days visiting Florence, 1 day Siena, 1 day Lucca, 1 day Volterra/San Gimignano.

Then, I could have 2 days elsewhere. Venice? Rome? Lake Como? Or, should I switch up the plan above? Any advice is appreciated.

Thanks so much!

Posted by
1550 posts

Sounds like you are well on the right track. I would stick with Tuscany, which does have a good bit of variety (lakes, seaside). Fly into Florence, go somewhere like Siena for a night, pick up car next day when you are rested, stay in agriturismo x days, then finish in Florence.

Posted by
1 posts

My recommendation for a romantic, shorter get away would be to fly into Venice, an incredibly romantic city, and then spend time somewhere on Lake Como. We stayed in Varenna, but I'm sure any of the towns around the lake would be wonderful. both are so beautiful and it's fun to hop on the ferry and visit other towns. The lake towns are hilly, but small. You won't get the cool, Medieval stuff like you would in Assisi, but I think it would be very romantic and fun. Happy Anniversary!

Posted by
3463 posts

All the towns you mentioned can be done as a day trip from Florence by either bus or train.

Will you be renting a car? Necessary for staying in an agriturismo.

Recommend this one for a romantic stay located just outside of Greve in Chianti.

https://www.verrazzano.com/en/

Posted by
55 posts

Yes, I will be renting a car. I'll add that to the original post as well. Thanks, I forgot to add that info!

Posted by
303 posts

Happy #15! I can't think of a more romantic experience than flying into Venice, spending 3 nights there and then taking the Frecciarossa train to Milan then a regional train to Varenna on Lake Como as suggested above. You could return to Milan to fly home. I can not tell you how absolutely breathtakingly beautiful the view of Lake Como and the distant Alps are from Varenna. Varenna is quaint, quiet and charming with a promenade along the shore that is so lovely. There are boat tours of the mid lake region; ferries to Bellagio and Mennagio, tours of Villa Balbianello or Villa Cipressi. Hotel du Lac is right on the shore with a terrace restaurant and some rooms with balconies.
This would be a 2 site stop and not a frantic 1 night stop at several. As a woman who just spent 4 days at Venice and Varenna this May, I can guarantee she will love this trip.

Posted by
55 posts

Okay - now two people have said Venice and Como so you have me thinking. I have a hard time missing Florence as I know many who have said Florence is their favorite city in the world.

What makes you both say (fairly emphatically I might add;) ) that Lake Como is a better stop than Florence/Tuscany for half of our stay?

Posted by
1550 posts

I think we all have personal favorites. The real question is what made you initially choose Tuscany. Either rural Tuscan villages/small towns OR Venice and the lakes would be a nice trip.

Posted by
303 posts

I respond on sheer emotion. I have not been to Florence, but have been to Rome, the Amalfi Coast, the Cinque Terre, Venice and Lake Como. Varenna on Lake Como is my all time favorite. This is to be a romantic trip. Only you and your wife can determine what you both consider romantic. Why don't you watch Rick's videos (the tv clips highlight these places so well) and familiarize yourself with the places you are considering? I would stick to 2 places so you can relax and soak up all that each place offers. I know it is hard to pare down destinations, but you have to hold on to the thought that Italy will call you back again.

Posted by
55 posts

Valadelphia and Barb -

Thank you so much for your thoughts, I value the input for sure. You asked what made me initially plan to do Florence and the Hill towns of tuscany, and there are several reasons. I thought that would be adventurous and somewhat romantic as well. Small quaint old towns where we could get immersed in Italian culture. Also, I felt like there would be plenty to see and do without tons of travel time between big cities (45 minute drive here, an hour drive there, etc).

I've always wanted to see Rome without just hitting all the tourist sites, but by walking through a smaller town and eating in a local restaurant. Many of you probably feel the same way.

With that said, I would be open to switching things up. It seems like doing Florence, Venice, and Como would be too much transit time. Particularly getting to Como because it's a several hour train ride to Milan, then we would have to catch another hour long train ride up to Varenna/Como. It seems like that would be something we could do if we were doing two stops (Venice/Como trip or Florence/Como trip), but not three - even though I keep trying to fit it in :)

Posted by
55 posts

Let me follow that up with - is there enough to do in Varenna area (ferrying to Bellagio, etc), to enjoy 3 days there?

Posted by
617 posts

Congratulations on your upcoming anniversary. You have already received some great suggestions. If you decide to stay just in the Tuscany region, there is plenty to see and do to occupy your 7 nights. My family and friends just returned from a whirlwind trip in Italy and spent 3 nights in Florence and 4 nights in a B&B near Siena and we wished we had more time.

  • B&B: Borgo Argentina is a lovely restored farmhouse with 2 villas 20 km north of Siena, http://www.borgoargenina.it. Elena is a generous host and they have a phenomenal cooking class (this is one of the reasons we chose this property). Make sure that you get one of the Villa’s. It is in the heart of the Chianti wine region and there are some very good wineries near by, including Barone Riscoli.
  • Wineries: Gerri already recommended the Verrazano winery to stay at (45 minutes from the Florence airport). We didn’t stay there, but had their tour and lunch (3+ hours) of fantastic wine and a Tuscan feast. Here is the link for the top wineries recommended by Food & Wine:https://www.foodandwine.com/slideshows/best-wineries-visit-tuscany. You do need to reserve in advance for tours and tastings.
  • Themal spas: Tuscany has some wonderful thermal spas and my friends and our girls wanted to do a spa day, we drove 1.5 hours south of our B&B and spent a day at the Spa in Bagno Vignoni and then went back to our B&B for a lovely 4 course truffle dinner at a restaurant near our B&B. Here is the link to thermal spa options (some natural and no charge, others a real spa), https://www.discovertuscany.com/itineraries-in-tuscany/thermal-itineraries-tuscany.html.
  • For Florence, it was really about seeing the Renaissance art, the Duomo, and experiencing the city at night. One of the highlights of our trip was taking the Evening Sunset Food Tour (small group of 8 people) and exploring a typical Florentine dining experience beginning with an apertivo and ending with dessert on the steps of a local church. We stayed in an apartment in Florence, so I can’t recommend hotels in the city.
  • Renting a car is easy and driving through Tuscany wasn’t taxing. Driving in Florence is a bit of an issue with ZTL zones (restricting traffic for local drivers). We opted to rent at the Florence airport and drive south into Tuscany and return in Siena and then catch a train onto Rome.

As you can see, we barely touched the surface. In fact, when we went to Siena with the girls, our friends just stayed at the B&B and relaxed. That is what we loved about Tuscany, the option of doing nothing.

Hope this helps in your planning if you opt for Tuscany.

Sandy

Posted by
303 posts

We spent 4 days in Varenna, and it was heavenly. We booked a private tour of the mid Lake region that also included a tour of Villa Balbianello. We spent time just walking around this charming village. We ferried to Bellagio and walked out to the point where the 2 legs of Lake Como join at Bellagio. We ferried to Mennagio and walked the promenade and had lunch. We toured the gardens of Villa Monastero in Varenna and walked the coast to a nearby village up the coast to see the milky river that flows from the mountain to the lake. We wished we had time to tour Villa Cipressi and the gardens. We sat at a cafe with a drink and watched the sun set over the mountains and lake. Our hotel room had a balcony, and the view of the lights on the water from the villages on the other side was lovely.
We wished we had taken a ferry or a hydrofoil all the way down to Como to see the entire leg of the Como side of the lake going past George Clooneys villa. We did take a bus down this coast going to the Como San Giovanni train station, and it was beautiful. As we walked the promenade in Varenna, we passed a man with a camera. He stopped to talk, and he summed it up, "There is no way any picture can do this scene justice. It is absolutely gorgeous." It is.

Posted by
77 posts

Given that you only have a week and your wife is a more reluctant traveler, I would consider renting a house/villa/apartment in Tuscany for the whole time. You're likely to have some jet lag the first couple of days and for a romantic, anniversary trip, no need to push yourselves to too many places. We found driving around the region to be really enjoyable and easy - visit wineries, take a cooking class, go on a guided truffle hunt (if they're in season when you're there) and just relax. We just back from Italy and wish we had more time to go back to Tuscany. It's a region that is well-deserving of its reputation. We were in Montepulciano and found that to be a delightful home base. Good luck and enjoy.

Posted by
3448 posts

Since you mentioned that you will be returning with your family in a couple of years, I would focus on the smaller towns on this trip and leave the major cities for your return trip. From what you’ve mentioned, flying into Florence and immediately driving to Montepulciano for several days and then staying at Florence your last two nights would be a good trip.

Personally, the most romantic places to me in Italy have been Venice and Stresa. Venice because it’s so special & unique; Stresa because it’s at Lake Maggiore with beautiful Isola Bella to enjoy seeing the romantic villa & garden. But almost every location we’ve been in Italy would be romantic with the fantastic food & culture. Enjoy & congratulations on your anniversary!

Posted by
11658 posts

Hi there, Drew!
Could you clarify something for baffled little me? You start your post saying...

7 nights maximum (need to get back for the kids)

...but then produced this sample itinerary:

My plan was to spend about 5 nights in an agriturismo just outside of
Florence (maybe max 30-50 minutes). Spend 2 days in Florence, 1 day
Siena, 1 day Lucca, 1 day Volterra/San Gimignano. Then, I could have 2
days elsewhere. Venice? Rome? Lake Como?

Er, I'm counting a trip of nearly two weeks. How many nights do you have, or how did I get all befuddled?

Posted by
55 posts

Kathy -
I see how it was confusing. What I meant was, 5 nights in an agriturismo outside of Florence for accommodations. Then, for our daily activities, that’s when I listed 2 days in Florence, 1 Siena, etc....

For a home base I’m looking at either 5 days Tuscany and visiting Florence during that stay - then doing 2 nights in Venice. Or, I may do 3 nights in Florence and then 4 nights in a Tuscany Agritursmo and just focus this trip on the area of Tuscany and all the towns around.

Posted by
11658 posts

Oh THAT'S how I got all muddled up! Thanks a bunch for clearing my fog, Drew!

I have a hard time missing Florence as I know many who have said
Florence is their favorite city in the world.

I'm one of those people...although it's running neck and neck with Rome. I don't know as I'd choose based on one location being more romantic, maybe, than another. Heck, keep your eyes open and you'll see amorous Italians and tourists alike having a smooch and a cuddle just about anywhere you go! I think it's something in the water. Or the wine. :O)

But taking your Best Girl's preferences into mind, a combo of agriturismo with a car for exploring some small towns, and Florence, with some day trips by train or bus, might just do it. That would keep the packing/unpacking to a minimum yet give you oodles of options with which to fill your time.

Posted by
334 posts

I'll be the naysayer and say I was underwhelmed with Venice. It's unique and has layers of history and culture but, I found it overwhelmed with tourists, the majority of the restaurants were turning and burning covers, the streets and hot spots were a mad house, I just didn't feel the charm. The early morning and evening was when things would calm down but, I totally get the frustration of the locals. If there's a next time, I would look into possibly staying out on the outlaying islands of Murano and Burano or, maybe on Guidecca.

Tuscany is my favorite region, Lucca in particular with it's great food, and not as humid climate as Florence. There's plenty of villas you can rent on AirBnB outside of town and soak-in the hill side splendor or, find a agratorsimo. Siena for sure is a great area and the smaller towns to the south particularly Montalcino which is in the heart of the picturesque Val d'Orcia. Volterra for sure, pass on San Gimignano.

Lake Como is a special area if you're partial to a more alpine region, Lake Garda is similar just not as upscale as Como.

Posted by
1804 posts

I would stick with your first choice, and visit Tuscany and then Venice. Admittedly some people don't like Venice, but others of us love it and have returned numerous times. It's one of the world's most unique places. Spend two nights there. Stay in a non-touristy area (Canareggio?). Be sure to get out in the early morning and in the evenings. That's when Venice is at its best.

Speaking of personal preferences, I was not a fan of Lake Como. It could have been jet lag -- this was our first stop in Italy that trip. Or maybe my bad knees ... there is very little flat walking there, with lots of steps to climb to get anywhere. It was undeniably beautiful but I found it a bit boring. If you do decide to visit Lake Como, I would highly recommend spending one day at the Il Caminetto cooking class. Chef Moreno picks you up and drops you off in Varenna, and you spend the day eating and learning and being entertained by this charming man. It was the highlight of our trip there.

Posted by
2436 posts

I'm in the "Florence is my favorite city" camp-I've been 3 times and stay longer every time. Florence is an enjoyable place to just wander around. Before scheduling time in Venice, you should check the cruise ship schedule to see if you can go when fewer ships are in port-all those crowds would make daytime very unromantic. I've never been to Lake Como so can't comment, but my one trip to Venice was enjoyable but not essential. Meaning, if I had never been, I would not regret it on my deathbed.

Posted by
55 posts

You all are awesome! Thank so much for all adding your thoughts.

I think I am going to stick with a Florence/Tuscany centric trip, with likely a small 2 day detour to Venice and fly out from Venice. Lake Como sounds awesome, and I would love to go, but I think that will have to be for a North Italy/Switzerland trip.

Now to decide between:

Option 1: Stay in an agriturismo that is 30 minutes or so from Florence (therefore closer to Siena, Volterra, Lucca, etc), and then drive to Florence when I want to see Florence. The negative of this is less time in Florence, and when in Florence we wouldn't be able to pop into our Airbnb to rest, etc.

Option 2 - Stay in Florence, and do my day trips from Florence. Negative - more drive time to get out to the hill towns, and likely less time in them as a result. Would be far enough away that likely would have to drop one, etc..

Posted by
11658 posts

Drew, a couple of questions?

So you have 7 nights total on the ground in Italy and that includes the night of arrival day?

That's more accurately just 6 full days in Italy: arrival day doesn't count as it's often a jet-lagged fog. Also, if your airport is some distance from your destination, you'll end up spending a chunk of that day getting there, and deal with a car/finding that place right off an international flight. You'll kill another 1/2 day or more transferring to Venice so now you have 5.5 days: 4 days/5 nights in Tuscany and 1.5 days/2 nights in Venice.

If this picture is accurate, does that influence your choice?

we would spend 2 days visiting Florence, 1 day Siena, 1 day Lucca, 1
day Volterra/San Gimignano.

As it is, with just 4 full days you'd have to drop something?

when in Florence (if not staying there) we wouldn't be able to pop
into our Airbnb to rest, etc.

True. Also, if you and your bride plan to enjoy the local grape, it can be very nice to be able to walk home after a romantic dinner w/a bottle of that, or get on a train?

Posted by
55 posts

So you have 7 nights total on the ground in Italy and that includes the night of arrival day?

That's more accurately just 6 full days in Italy: arrival day doesn't count as it's often a jet-lagged fog. Also, if your airport is some distance from your destination, you'll end up spending a chunk of that day getting there, and deal with a car/finding that place right off an international flight. You'll kill another 1/2 day or more transferring to Venice so now you have 5.5 days: 4 days/5 nights in Tuscany and 1.5 days/2 nights in Venice.

If this picture is accurate, does that influence your choice?

Great points. Yes, giving up a half day out of 6 to travel to Venice would be hard, and maybe not worth it. I have been a little on the fence about trying to add Venice to this trip anyway, and you make good points.

As I said earlier, we don't like to travel fast. Travel slow is much better for us. Staying in Tuscany and Florence for our 6 days may be the best bet - plenty to see.

True. Also, if you and your bride plan to enjoy the local grape, it can be very nice to be able to walk home after a romantic dinner w/a bottle of that, or get on a train?

I'm not 100% sure which side you are landing on. Are you saying that it would be much more romantic and convenient to be staying in Florence and not have to grab a train or drive back out to the countryside? The opposite is true though as well. What if we have a great dinner in a small town 45 minutes outside of Florence, and then we have to drive back into the city for our airbnb. That's not ideal either.

I'm thinking the best bet is 3 nights in Florence, 4 nights in agriturismo. Minimize travel time all around because my "hill town" portion of the trip we would have accommodations much more centrally located than Florence is. And, cut out the travel to Venice.

Tough decisions with limited travel time!

Posted by
996 posts

Okay, this is just personal opinion, and YMMV, but....

If I had 7 nights on the ground (not including flying to/from Italy) I'd pick one spot (like Florence) as my flight destination. I'd next head to my Tuscan agritourismo and do day trips from there as needed....and then return to Florence for a night before flying out the next day.

That's just me, though. I hate having to unpack at each place.

ETA: Happy anniversary!!!!

Posted by
55 posts

Okay, this is just personal opinion, and YMMV, but....
If I had 7 nights on the ground (not including flying to/from Italy) I'd pick one spot (like Florence) as my flight destination. I'd next head to my Tuscan agritourismo and do day trips from there as needed....and then return to Florence for a night before flying out the next day.
That's just me, though. I hate having to unpack at each place.
ETA: Happy anniversary!!!!

Thank you! And I agree. My max number of accommodations is 2. I’m not moving twice to stay in 3 locations on that short of a trip.

So you are saying you would fly into Florence, upon arrival drive out to agriturismo and stay there the bulk of the trip, then drive back into Florence on the night before our return flight (or maybe a couple nights before for more time in Florence).

That’s kind of what I’m feeling right now too.

Posted by
11658 posts

I'm not 100% sure which side you are landing on. Are you saying that
it would be much more romantic and convenient to be staying in
Florence and not have to....drive back out to the countryside?

It's something to think about, maybe? Call me crazy but a fair amount of people I read about who choose an agriturismo do so to spend time at an agriturismo. Not ALL of their time, certainly, but enough of it to warrant the rural location and car rental. Some enjoy the activities/amenities these accommodations sometimes offer (cooking classes, pools, horseback riding and whatnot). Others just want to kick back for a day or two and enjoy the view. Your proposed agriturismo stay looks pretty full of day trips that will have you gone all day, every day, except the one you arrive?

Then there's what you want to DO with your time, including the evenings? Personal preference but we REALLY like meandering Italian towns and cities at night and in the early mornings as they have a different ambiance than during the day. The activities/sightseeing we most enjoy are also IN towns and cities: the piazzas, museums, churches, architecture, street music, markets, etc. so those make better bases for us versus a rural setting, lovely as they can be.

I brought up the wine because while one certainly doesn't HAVE to indulge in alcohol, a shared bottle or couple of pints is a pleasure for many. Personal preference again but having the freedom to do that and not have to get behind the wheel - especially in a foreign country - can be one consideration when choosing a base and method of day-tripping? Sure, if your agriturismo offers dinner and so you abstain until then, no problem. That said, we'd more comfortable hopping a train for the day and have that option of going 'home' again, should we decide to indulge...which we do often enough. If we're basing in a town or city, we also have a varied offering of restaurants to chose from and the ability to walk to an accommodation.

Anyway, there's no right or wrong to it except what works for YOU, your style of travel and your interests: it's YOUR trip! I'm just throwing out some weights and measures that might help you make choices?

Posted by
1666 posts

With all the above information, how would you design a trip? My plan was to spend about 5 nights in an agriturismo just outside of Florence (maybe max 30-50 minutes). During the days we would spend 2 days visiting Florence, 1 day Siena, 1 day Lucca, 1 day Volterra/San Gimignano.

Drew,
Two years ago my wife and I did just what you are thinking about. We were also celebrating an anniversary. We were celebrating our first kiss which we shared in Florence, in 1966! 50 years later we shared another kiss in Florence.

Here's our itinerary, given as an example:

We flew into Rome FCO because we could get the best airline ticket prices. We picked up our Hertz rental at the airport. I bought a card for my Garmin that has maps of Italy and Greece. Before we went, I saved a number of addresses, including the address of our agriturismo. As soon as we picked up the rental car, we set up the Garmin, pulled up the saved address and were taken on a wonderful drive to our destination.

We stayed at Castello di Verrazzano, which is 5 minutes north of Greve and 35 minutes south of Florence. It is a great winery and there is a farmhouse complex just down the hill from the castle and winery that they use for their agriturismo. After checking in, we rode down to the charming town of Greve, looked at the Christmas fair (we went in December) and had a great dinner at La Cantina.

We figured we'd be tired, so for our first full day on the ground we took a tour of the winery of Castello di Verrazzano, along with a food and wine tasting. Our tour started at 11:00 and we sat down for the tasting at 12:30. We didn't leave until 4:00! It was an amazing meal. Luckily we were staying on the property because they were generous with their wine!

Day 2 we drove down to Greve and parked in the free public lot. We caught the 6:45 bus to Florence, which is a 35-40 minute ride. Everyone else on the bus were locals commuting to work. Once in Florence, we took the Walks of Italy Best of Florence tour. We saw the Duomo and David in the morning, along with a great walking tour of the heart of Florence. In the afternoon we took a Walks of Italy tour of the Uffizi. We took a late bus back to Greve.

Day 3 was a Tuscan ramble south of Greve, including the charming towns of Radda and Gaiole. We ended up at the Abbey of Monte Oliveto mid afternoon. After taking a tour of the Abbey, we had dinner at the adjoining restaurant. Our host spoke no English, but by using our extremely limited Italian and pointing at the menu, we were able to order a wonderful dinner. We returned to the Abbey for Vespers celebrating in Gregorian Chant. There were the monks, one woman from a nearby village and us. We were invited to sit with the monks and were shown the responses where we could participate. It was a very moving experience!

Day 4 had us head southwest to Siena, passing through Castellina on the way. Siena is very different from Florence and we had a wonderful time!

Day 5 was a great drive to San Gimignano and Volterra. We started with San Gimignano in the morning and spent the afternoon and evening in Volterra. We had planned to leave late afternoon, but we went outside the walls to the town's promenade. The sunset on the town was spectacular and we stayed to watch it. I photographed until dark and came back with one of best photos from the trip.

Day 6 had us say goodbye to Tuscany and drive back to Rome. We had and early flight and decided to stay at the FCO Hilton. We checked in and I returned the rental car. We then took the free hotel shuttle into Rome. We took the Walks of Italy evening stroll and had a wonderful time. It was the last Saturday before Christmas and all the locals were out shopping. It was crowded, but everyone was in a festive mood!

Posted by
55 posts

Kathy -

It's something to think about, maybe? Call me crazy but a fair amount of people I read about who choose an agriturismo do so to spend time at an agriturismo. Not ALL of their time, certainly, but enough of it to warrant the rural location and car rental. Some enjoy the activities/amenities these accommodations sometimes offer (cooking classes, pools, horseback riding and whatnot). Others just want to kick back for a day or two and enjoy the view. Your proposed agriturismo stay looks pretty full of day trips that will have you gone all day, every day, except the one you arrive?

This is a good point, although quite honestly most of the reviews I read of trips where people are staying in agriturismos, its so that they are out in the country, and can travel around to the different towns during the day via car. I would certainly spend some time on property hopefully taking in a meal, having breakfast, etc, but I wouldn't expect to ever spend a whole day there. I guess I didn't think most people did :)

Then there's what you want to DO with your time, including the evenings? Personal preference but we REALLY like meandering Italian towns and cities at night and in the early mornings as they have a different ambiance than during the day. The activities/sightseeing we most enjoy are also IN towns and cities: the piazzas, museums, churches, architecture, street music, markets, etc. so those make better bases for us versus a rural setting, lovely as they can be.

Your comments above and here have made me think - because you make good points. Yes, we would enjoy wandering around in the morning and evening as well. Which is different if you need to drive 25 minutes to get to the town of choice for that day. Maybe a B&B or hotel inside one of the small-to-medium size Tuscan towns would be best. Thanks for your thoughts here, really making me second guess things - for the better!

Posted by
567 posts

We love to travel but have several family members who are nervous to various degrees about traveling. It definitely helps them feel more relaxed to stay in one place, two at the most, and to minimize transportation, especially public transportation.

My thought is for you to fly in and out of Florence because the Florence airport is small and close to town and it's cheap, quick, and easy to take a taxi into or out of Florence --- the Rome, Milan, and Venice airports are not like that. Also easy to rent a car there and drive out of the city.

I would not describe Florence as small, quaint, or cute, although we love Florence and have spent a total of six weeks there. And hope to return for additional weeks some day.

Having just spent 5 nights in Siena in April, just the two of us after a busy two week family trip in Puglia, I'm thinking that may be your best base. Smaller, cuter, quainter.

Rent a car at the Florence airport and drive to Siena and park it either in one of the parking garages right outside the walls or (less expensive but a bit more of a walk) in one of the large parking lots outside of the medieval walls and down the hill (in at least two places there are escalators up and down). You don't need to stay at an agriturismo to have a place to park.

In Siena, we stayed at an airbnb apartment we really liked near the medieval city gate that is closest to the train station. Quiet, interesting pedestrian-only street. Lots of good restaurants and coffee bars and gelato shops. Lots of things to do and see in Siena so we didn't even do any day trips this time. There are nice B&Bs in Siena, too, if you like having breakfast made for you, and somebody cleaning your room (I don't).

I'm pretty sure there was a parking garage at the Siena train station. And the longest series of escalators we've ever been on.

Then, after Siena, spend your last night or maybe your last two nights in Florence --- it's just always smart to stay in the city you are departing from. Take a taxi from wherever you drop off the rental car and take a taxi to the airport for your flight home. People who do not "love travel" do not seem to find it romantic or fun or adventurous to figure out public transportation or to be in train or metro stations or at bus stops in foreign countries, so we've found it best to just spend money to keep them more comfortable.

Good idea to design the trip around your wife --- this is what we tried to do when taking our son, daughter-in-law, and their preschooler and baby to Italy, and we mostly succeeded (our only museum was a train museum, for instance!)

Posted by
616 posts

If you decide on Florence and Tuscany,
I would dedicate four days in Florence, preferably in a beautiful apartment in the Centre or oltrarno (Pitti, Piazza Santo Spirito). Make sure you get a lift and air conditioning. In Florence a car would ne a nuisance
You can then go to Sienna, stay there for two nights ( easy connection by bus, easier than train, and it will give you an idea of Tuscan landscape already)
or rent a car and go to an agroturismo in Val d’Orcia. This will be very romantic and enough.

Posted by
55 posts

Wow, great advice nancyscherer8! So helpful. I'm reworking my itinerary and accomodation plans according to all of the great advice I've received in this thread. Thanks!

Posted by
228 posts

I concur with the poster above who suggested Venice and Como. My wife and I just got back from a one-month trip which included both, and we celebrated our 43rd wedding anniversary in Bellagio, at La Punta restaurant (highly recommended).

Both places are romantic, though I don't think you need more than 3-4 nights in Venice. Bellagio, OTOH, is located on Lake Como and so it is easy to board a ferry and visit other places on the lake, so a week would be perfect, I reckon.

Of course you must acknowledge that both Bellagio (and to a lesser extent, the other lakeside villages) and Venice are very touristy. This did not detract from the joy for us, but sightseeing in Venice is best accomplished early in the day. The rest of your time can be spent in relative peace if you just stray 100 yards off the main tourist trail, into lovely old streets (and much less expensive eateries).

One negative surprise for us was the Venetian gondolas, which did not look as romantic or appealing as we expected. This was not the fault of the gondolas themselves but the crowded waterways, where hundreds of water taxis churned the water up and tossed the poor gondolas around. If you could stick to the very narrow and less busy canals it might be OK, but you might miss the icomic landmarks that way. We decided not to bother.