Best Towns in Tuscany – Tips for a Perfect Trip

I think it’s ambitious to say that there is a single travel guide can point you to all the best towns in Tuscany.  In fact, I don’t think there can be one single blog post on anything (but particularly a travel destination) that can fully inform you of everything.  I’m realistic about that fact.  If you’re anything like me, you draw inspiration from multiple sources, books, blogs, videos, and photos.  There are a lot of beautiful towns in Tuscany (and Umbria).  Every time we go, I fall more in love with the region and find something new to love.  It’s a big region.  In fact, when we ended up in Tuscany in December 2018, we were able to get further off the beaten track and explore different areas of northern Tuscany, as well as southern, eastern and central Tuscany.  There is still a lot to explore.

NOTE:  You won’t find Florence covered in this post, but there’s plenty of Florence travel information on this blog. I’m choosing to focus this post on the smaller towns of Tuscany.  As I was choosing photos for this post, I realized that I may need to do some additional posts on different parts of Tuscany because I have a lot to share!  If there’s something you want to hear more about, drop a note in the comments.  

If you’re looking for a great one week in Tuscany itinerary (including Florence), Maggie has a great post on this!

Disclosure:  This post contains affiliate links for tours and products I love at no additional cost to you.  You can read my full disclosure policy here.

Best Towns in Tuscany to Stay and Play

Let’s just be clear: there’s Tuscany and there’s Florence.  I love both and want you to experience both.  Yes, you can take day trips from Florence, but the experience isn’t the same.  If you want to truly enjoy Tuscany, I recommend finding a home base and exploring the region with a car.  My favorite thing to do is to pair larger Italian cities with a small town.  Seriously.  Give yourself more than one day in Tuscany.  

I have a number of favorite hotels in Tuscany, but it depends on the experience you are looking for.  If you want to stay in a town that offers plenty of restaurants and things to do, I recommend Cortona, Montepulciano and Siena. You can’t go wrong with either.  They seem more “real” and “lived in” to me.  Pienza and San Gimignano can feel too “postcard perfect,” though they are lovely.  You should still visit though.

Where to Stay in Cortona

If your anything like me, you might be avoiding Cortona because of the Under the Tuscan Sun fame.  I thought it would be too touristy.  Turns out, it’s incredibly lived in and absolutely stunning.  We visited for the first time time in June 2021 and immediately booked a longer return trip in October 2021.  

We stayed at the Monastero di Cortona Hotel and Spa on both trips, and I will definitely be returning.  This beautiful hotel at the top of town is absolutely gorgeous, offers an incredible spa, and the best service around.  Our room faced west and each night, we were treated to a breathtaking sunset.  The beds are some of the most comfortable in Italy, and the linens are so very soft.  I would argue the sleeping experience rivals my favorite St. Regis Florence.  Guests are required to be 13-years-old or over, so it would be a wonderful honeymoon hotel in Tuscany, too.  

Breakfast is included with your room rate and takes place in an incredible room of frescos – or you can enjoy it on their terrace with a view of the pool.  They also offer a small on-site bar, if you’re looking for a nightcap after a delicious meal in Cortona.  (Yes, you have to walk uphill to get there.  Yes, it’s worth it.)  (Read all about the Monastero di Cortona Hotel and Spa amenities!)

The Monastero offers an on-site garage (with reservation), which makes unloading very easy.  Just make sure you book a small rental car.  We had a Jeep on our first trip to Cortona, and I had to walk down the hills to direct Tom.  Our smaller Fiat 500 in October did the trick though!

I think it’s safe to say that the Monastero di Cortona has become my favorite hotel located within the hill towns of Tuscany.  I’m looking forward to checking out their sister hotel in Rome!   

Read More: Where to Eat in Cortona, Italy

Where to Stay in Montepulciano

Update:  Full review on our multiple stays at Palazzo Carletti.

Given my appreciation for exploring small towns at night, I knew I wanted to stay in Montepulciano on our first road trip to Tuscany.  It seemed a bit more lively than some of the other cities I considered.  (They even have a Christmas market in December!)  There are several local wineries that offer tasting (no driving or drivers required) and one of our favorite restaurants in Tuscany is in the heart of Montepulciano.  On our most recent trip. our room had a view of the countryside and we spent our mornings watching the sunrise.  There are also many beautiful churches to explore in Montepulciano.

When it comes to where to stay in Montepulciano, Palazzo Carletti is the perfect location.  It’s a short walk from the main square  The beautiful rooms and fancy bathrooms are merely bonuses, given the rustic location.  With frescos on the ceilings, large windows, and palatial finishings, it’s easy to feel like you’re living in a palace.  When you add in the free parking, free mini-bar and included breakfast, it’s a great deal.  The staff are the most wonderful hosts and hostesses; they provide everything you need to know about parking and check-in before arrival and seek to make every detail of your stay perfect.

STAY:  Palazzo Carletti 

Where to Stay in Siena

Update:  Read more about how we kept busy on two trips to Siena and check out more photos of our hotel.

Siena is a medieval town that shouldn’t be missed after the day trippers head home.  (The whole city is a UNESCO World Heritage site.)  A lot of people compare it to Florence, but I think it’s completely different.  (I love them both.)  Siena is more lively than Montepulciano but not as frantic as Florence.  If you’re looking for decent shopping, plenty to see, and great people watching, choose Siena.

For two years, we have stayed at La Terrazzo sul Campo.  You will not get any closer to the town centre.  It overlooks the main square in Siena, il campo.  The view from the room is worth the visit alone, especially at sunrise.  If you booked it for that reason alone, I wouldn’t fault you.  The rooms are spacious, bathrooms are modern, and the beds are firm (and comfortable).  Truly, the best part about this hotel, however, is Viola and her brother.  (Viola even remembered us from our previous stay!)  They go above and beyond to make your stay comfortable.  Breakfast is included, custom, made-to-order, and even when we forgot to turn in our order the night before, they were happy to accommodate us.

The parking garage is inside the city walls and about a 10-minute walk from the hotel.  We didn’t have any trouble bringing our luggage up to the city centre.  (To be honest, it was WAY easier than transporting our luggage in Montepulciano.)

STAY:  La Terazza sul Campo

Restaurants in Tuscany to Try

Acquacheta Montepulciano

We all know I love bistecca Florentine.  It might have been what I was most looking forward to when I started planning a trip to Tuscany.  I scoured restaurant reviews, photos, books, and blogs to find where to eat in Tuscany.  All roads led to Montepulciano.  All roads led to Osteria Acquacheta.  When we arrived in Montepulciano and found that it would be closed the entire time we were there, I was disappointed.  After we had relocated to Siena for the second part of our trip to Tuscany, my husband convinced me that we should drive to Montepulciano for lunch.  I was dubious.  Could it really be that good?  Could a steak be so good that it was worth driving in the rain for over an hour? 

Yes.  Yes, it could.

I recommend anything on the menu (or ask Gulio for his recommendations), but do not miss the pici pasta with fried garlic and chilies.  We told the waiter to “cook it the way Italians like it.”  He chuckled and brought us the most delicious steak.  We ordered the toasted bread with olive oil, the cured meats, the bistecca, the pasta, water, and wine. It cost less than 75 euro.  Is it a splurge meal?  Yes.  Is it worth every penny?  Yes.  If you eat one meal in Tuscany, let this be it.  (We’ve tried other places.  This one stands on its own.)

EAT & DRINK:  Osteria Acquacheta

WARNING:  This has become a common detour on our Tuscany road trips.  We’ve been known to detour to Montepulciano for this meal.

Cafe Poliziano Montepulciano

Alternative titles to this section: best cafe with a view of Tuscany or best place to warm up on a cold, rainy day in Tuscany.  On our first trip, we did not have the best weather when we were in Montepulciano.  In fact, it might have rained EVERY single time we were in the city.  Fortunately, it wasn’t non-stop torrential rain, but it did make for cooler, damp days.  

Cafe Poliziano provides a great place to warm up and enjoy a coffee or a pastry.  If the weather is nice, there is a balcony with a view.  (Even the view with the fog was lovely though.)  It reminds me of some of my favorite cafes in Vienna – dark, elegant decor, delicious pastries, and fancy coffee drinks.

EAT & DRINK:  Cafe Poliziano

Poderuccio Pienza

Have you really been to Tuscany if you haven’t had a meal at an agriturismo?  I’m going to say no.  Located a few minutes from Pienza is Poderuccio.  You need reservations, but it might be possible to get them the day of in shoulder season.  (We’ve been turned away in December.  Make reservations.)  

Antonio is delightful. Bring your Italian skills or phrasebook.  The menu changes based on what’s in season.  I recommend any kind of homemade pici pasta.  Tom really enjoyed trying the wild boar pasta. Again, try what Italians recommend: it’s a regional thing.  Portions are large and filling; bring your appetite.

EAT & DRINK:  Poderuccio

Caffe Sant’Angelo Montalcino

If you’re out and about trying the Brunello di Montalcino, make sure to stop by Caffe Sant’Angelo for a delicious meal.  It’s not in the city center, so you’ll need a car (or driver) to get there.  The handwritten menu changes daily and with the season.  

Caffe Sant’Angelo is inexpensive, hearty and fresh.  I really enjoyed my fresh spicy pasta with pecorino.  You’ll want your Italian phrasebook to help translate the menu.  The staff speaks limited English, but you can get by with some Italian.  We spent our lunch surrounded by locals and I wasn’t mad about it.

EAT & DRINK:  Caffe Sant’Angelo

La Proscuitteria Siena

La Proscuitteria is the perfect place for a snack.  The wine is cheap, you have to grab a seat as soon as you can find it, and they don’t serve you, so don’t expect a restaurant meal.  (It’s also part of a chain, but don’t think of it like a U.S. chain – the food is all fresh!)  We dined on the most delicious open-faced sandwiches with fresh bread, olive oil, proscuitto and poppy seeds!  If you’re looking for a snack to hold you over, this place is fantastic.  (We also enjoy the Florence location.)

EAT & DRINK:  La Proscuitteria Siena

Siena (Hamburgeria al Buongusto)

After being burned by a terrible bistecca (burned American style), Tom convinced me that we should try Hamburgeria al Buongusto for a late night dinner.  I was resistant.  I did not come to Italy for a hamburger.  

It happens to be one of the only places open late though, which is how we found ourselves standing in line at a sandwich counter in Italy.  No one spoke any English. The man behind Tom told him which bread to choose and helped him order.  We walked down to a piazza where we could sit down and I sunk my teeth into the most delicious burger I’ve ever had in or outside the United States.  Everything was fresh and made to order.  And – like most good food in Italy – it was cheap.  (I’ll be back to try the bistecca.)

EAT & DRINK:  Hamburger & Steakhouse al Buongusto

Best Gelato in Tuscany

Buon Gusto Pienza

I don’t know who goes to Italy and doesn’t get serious about gelato.  (I wrote a whole post dedicated to my hunt for the best gelato in Cinque Terre for goodness’ sakes!)  Gelato is a mainstay for me.  I’ll happily skip a meal for gelato.  By the end of one of our trips, I think I was doing exactly that.  I think I had gelato three (maybe four) times on our last night in Rome.

A short drive from Montepulciano is the tiny town of Pienza.  Pienza is lovely.  It looks like something out of a Disney movie.  It’s almost too perfect, if you know what I mean.  But, there’s one reason to go back to Pienza again and again, and it’s BuonGusto.  

This man makes good gelato.  Again, I was dubious.  It seemed fancy… and by that, I mean he had fancy flavors.  I didn’t trust fancy gelato.  The first time I went, he didn’t have anything “normal,” but he recommended the saffron.  Fortunately, I had experienced a palate-changing food tasting moment in San Gimignano, so I was up for the adventure.

Oh my stars, it was good.  So good in fact that we drove back to Pienza on the way to Assisi (that is, completely out of the way) so I could have it again.  EXCEPT there was no saffron!  (He told me if I came back the next day, he would have saffron for me.)  BuonGusto makes his flavors fresh every day, so on that, he recommended that I try his strawberry and his orange-lemon.

And that, my friends, is why I refused to eat gelato that wasn’t sorbetto for the rest of the trip.  (I still dream of his flavors.  I even tried a kiwi-spinach-pear flavor on my most recent trip.)

EAT & DRINK:  Gelateria BuonGusto

Gelateria Kopakabana Siena

This first time we were in Siena, I walked across the city in search of the best gelato only to be let down.  Multiple times.  (Some places close early during the “off season,” and some aren’t open at all.)  This time, I was determined to find good gelato.  I knew it had to exist.  There had to be one place that was good (even if it wasn’t as good as BuonGusto).  

Enter Kopakabana.  Did you laugh at that?  I did.  This gelato is no laughing matter though.  It’s rich, creamy, and cheap.  Get the nocciola (hazelnut).  If you’ve already been to BuonGusto, try any of the sorbetto.  Why can’t we make ice cream like this in the states?!

EAT & DRINK:  Gelateria Kopakabana

Best Tours of Tuscany

In addition to scenery, Tuscany is known for its delicious products: wine, olive oil, meats, and cheeses.  Those are all things my husband I both love.  I knew food tours would be in our future.

Olive Oil & Wine Tasting in San Gimignano

On our first trip to Tuscany, I found a wine, olive oil, and balsamic vinegar tasting, and I booked it immediately!  It was scheduled to be a stopover on our drive to Montepulciano from Cinque Terre.  It seemed like a great way to break up the trip.  I wasn’t wrong.  When we traveled to Tuscany over Thanksgiving, I booked it a second time and we took my mom with us.

A short walk from the historic town center, this vineyard overlooks the rolling hills and the towers of San Gimignano.  (They will provide detailed instructions when booking.)  The hospitality from the staff is incredible.  Illaria provided us a tour of the vineyard, the history of their winery, as well as the correct way to taste wine.  (We learned so much in a short time!)  In contrast with other wineries in Tuscany, we started our tasting with white wine (named after one of the winery dogs!).  The tasting includes a multi-course meal, which we didn’t expect but really enjoyed.  

On both trips, the first course included a few different seasonal and traditional bruschetta, including tomato, olive oil and salt, pate, and purple cabbage. 

In the fall, we were able to try the traditional pappa al pomodoro (a tomato bread soup that I love), as well as a pasta dish.  Our fall meal was a roasted red pepper penne sauce, while the spring meal offered a fresh bowtie pasta with a classic tomato sauce.  Regardless of season, the red wines complemented the pastas perfectly.

Following lunch, we were able to try different olive oils and balsamic vinegars. (Saffron and truffle were my favs!)  Ilaria provided us a selection of different salami and pecorino cheeses to try with the olive oils and vinegars.  This tasting was accompanied by another red wine.  Once we finished those savory treats, Illaria had another surprise for us – cantucci and vin santo (traditional almond cookies with sweet wine)!

In the end, we purchased several products (which I shipped home) from the winery.  We didn’t feel rushed or pressured to buy anything. The goods arrived in the U.S. shortly after we did.  When DHL delivered a broken bottle, the company replaced it immediately.  I highly recommend this tour if you enjoy oil, vinegar, and wine.  (Our family orders from this winery regularly now.)  

BOOK THIS:  Olive Oil, Balsamic Vinegar, and Wine Tasting Tour in San Gimignano

Arezzo Wine Tasting

Real talk: This wine tasting tour taught us that we underestimated the difference between driving distance and time.  Arezzo is only 32 miles from Montepulciano, but it took us over an hour to get to the winery.  Once we got to Arezzo, we thought we would be at the winery within 10 minutes and called to let them know.  Thirty minutes later, we rolled up.  Yikes.  

They had already started the tour of the vineyard, but we were able to catch up to them and they didn’t mind getting us up to speed.  Our tour was during golden hour, and the views of the countryside were unparalleled.  The most interesting part of this winery is learning how self-contained and eco-friendly it is.  It’s the most environmentally-conscious business I’ve ever visited.  Every part of the process is remarkably thought out in the name of sustainability.  Most of the people on the tour were there because they knew about the sustainability and wanted to learn more about it.  The wines were a secondary interest.

After a tour of the vineyard and the facilities, we were escorted into a beautiful dining room overlooking the vineyard for tasting.  Similar to the San Gimignano wine tour, we were provided with instructions on how to hold our wine glasses to prevent temperature transfer and how to appropriately taste wine.  They served fresh bread, olive oil, cold cuts, and cheese with the wines.  

My only regret is that the rose was not ready for tasting – a college student on our tour who was studying abroad in the area said it was absolutely delicious.  I would have liked to try it!  We purchased a bottle for later (while others sent CASES home).  The prices were incredibly reasonable.  

Oh Italy…. where wine is cheaper than anything else.

BOOK THIS:  Wine Tour in Arezzo

Siena Walking Tour

To learn more about Siena, its contrade, and its history, I highly recommend this walking tour.  It offers a great introduction to the medieval city, and you might even get to visit one of the neighborhood contrade museums, which aren’t typically open to the public!  The tour starts in the campo and shares more about the Palio, before winding through the city streets and learning more about the contrade in Siena. We were able to visit one of the neighborhood  museums and see an exhibit on the historical Palio costumes, flags, and tapestries depicting the win of a particular contrade.  This tour provides an incredible look into the history of Siena and its “neighborhood” pride, especially if you can’t travel during the Palio events! Our guide also included a quick stop for tasting the ricciarelli, the traditional Sienese almond cookie.   

This tour highlights beautiful, “hidden” views of the Tuscan countryside, and follows the winding narrow streets to the Siena Duomo.  In retrospect, I wish we had included the Duomo tour, but we have used the audioguide in the past, and we knew that guides were not allowed in the Piccolomini Library, so we opted out.  I would add that option next time.  

Other Siena tours I would add to our itinerary?  This Siena food tour.  I tried and tried to add it to our itinerary and couldn’t make it work with our schedule.

BOOK THIS:  Siena walking tour

BOOK THIS:  Skip the line for the Siena Duomo

Tuscany Travel Tips

The best advice I can give you as you roam around Tuscany is to pop into every church you find.  Venture down small alleyways.  Explore.  Get lost.  You never know what you’ll find.  One of my favorite churches is in Montepulciano and none of the three famous guidebooks mentioned going into it.

On our first trip to Tuscany, we used trains to navigate to the “touristy” Tuscany and it was fine.  That said, renting a car gave us so much more flexibility.  It was really nice to be able to stop whenever we wanted to explore, take photos, get more gelato (Buongusto), etc.  The buses are more convenient than the trains, but a car gives you the most (and best) flexibility in Tuscany.  We had no problems with it and put together a few tips for driving in Italy.

If you plan on doing your own driving tour in Tuscany, the easiest thing to do is download Google maps and rent a mobile hotspot.  TEP offers unlimited wifi (way cheaper than a data plan!) and we’ve yet to find a place it doesn’t work.  Eventually we decided to purchase a Solis hotspot (save 10% with code JOURNEYOFDOING) so we own our own device.  Both mobile hotspots are great options when traveling abroad.  

Google maps does a great job of directing us, even on the small roads.  I know you can download google maps offline, but the wireless capability is good for navigating traffic and making sure that you aren’t taking up all the memory on your phone!

Listen, Learn & Read More

Listen

If you want to DIY your own walking tour, Rick Steves has free audio walking tours available for download.  The Siena city walk includes a walking tour inside the Siena Duomo.  Make sure you don’t miss the Piccolomini Library.  The frescos are some of the most beautiful I’ve ever seen.  The colors are so rich and vibrant.  Absolutely breathtaking. His app offers snippets of his radio show as well.  We’ve learned a lot and gotten a lot of ideas from listening to it.

Learn

We use the Rick Steves Hill Towns book religiously in places where there aren’t a lot of tour option in the off-season.  I think you get more out of a local guide, but this book gives you perspective on what you are seeing.  We particularly enjoy the self-guided tours of the Siena Duomo, the walking tour of Montepulciano, and the scenic driving tours of the area.  If you’re going to Florence, you can get his Florence and Tuscany book.  (They have A LOT of overlap; you don’t need both.)  I also like the Day-by-Day Florence and Tuscany and Top 10 Florence & Tuscany guidebooks.  I’ve also enjoyed thumbing through the DK Florence and Tuscany Travel Guide, but it doesn’t have a lot of information.

Read More

We love Tuscany and have made it a regular stop on our Italy itineraries.  If you’re looking for more Tuscan hill towns to visit, what to do when you visit Tuscany, or more ideas to make your trip memorable, please check out the links below.  If you’re looking for ideas on Florence, I’ve got you covered there, too.