I’m excited to share this post on the hill towns of Italy! I actually started working on the idea for this post during our (extended) winter trip and I’ve updated it after every trip since. We spent a few days road tripping through Tuscany and, in between visiting these Italian hilltop towns, we would recap our adventures. When we first started trying to decide where to stay on our first trip to Tuscany, I felt overwhelmed by the sheer number of towns and villages to choose from. Honestly, all of these hill towns are great. They are all beautiful in their own right. I encourage you to read through all of them before you make a choice on where to make your home base in Tuscany. If you can, choose one or two! I’ll make recommendations where I have them, but Tuscany is truly a choose your own adventure kind of place!
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Video Inspiration of the Hill Towns of Italy
Where to Go in Tuscany
The Classic Italian Hill Town Experience
STAY HERE: Monastero di Cortona Hotel & Spa
EAT & DRINK: La Bucaccia
EAT & DRINK: Trattoria Dardano
DON’T MISS: Basilica di Santa Margherita
DON’T MISS: Gelateria Snoopy
At the risk of taking on every single American cliche due to the success of Under the Tuscan Sun, we fell in love with Cortona. Maybe it’s because we visited in June 2021. Maybe it was the beauty of our hotel, Monastero di Cortona. Or, maybe it was the beauty and simplicity of apertivo hour. Regardless, Cortona felt special and we’re already planning our trip back. We’ve been 4 times, and I can’t get enough of the Monastero di Cortona!
I would hardly consider Cortona off the beaten track given it’s popularity, but it certainly felt that way when we were there. In restaurants and on the main square, we were surrounded by Italian. The city felt alive and “lived in,” in a way that some of the more popular hill towns in Italy seem to be lacking. We would start each day with a walk through town, including an intense climb to visit the churches in the northern points of town. Don’t miss the Basilica of Santa Margherita. It is, perhaps, the most beautiful church I’ve seen in Tuscany. It is, at the very least, tied with the Piccolomini Library in the Siena Duomo. After a mid-day nap and spa treatment, we would start our evenings with a passeggiata, pause for an apertivo, and wrap up the evening with dinner and gelato.
There is no shortage of delicious restaurants in Cortona. We found that it was helpful to allow the wait staff to make recommendations when we could not make a decision. In doing that, we ended up with an incredible sausage dish, as well as a truffle pasta that the owner assured us we would not forget for the rest of our life. (I will not. It was THAT GOOD.) Our only regret is that we didn’t have the stomach space to try more restaurants. We will be back.
Check out my Cortona Travel Guide!
STAY HERE: Palazzo Carletti
FOOD & DRINK: Osteria Acquacheta
DON’T MISS THIS: Montepulciano Christmas Market
With four trips to Montepulciano under our belt, this is one Tom’s favorite hill towns of Italy. It’s certainly one of my favorites, too. The hills give me flashbacks to Cortona and Cinque Terre though! I think it’s one of the most classic hill towns of Italy, but unlike some of them, it feels “lived in.” You see more than just tourists going about their daily business.
We have visited Montepulciano in April, June, November and December and loved each time equally. Surprisingly, it did feel warmer in December than in April! In December, there is a fabulous Christmas markets in Montepulciano that runs from the fortress at the top of town to the main square. We actually purchased some Christmas gifts, as well as a beautiful handprinted Christmas ornament, at this market. There is a wonderful wine bar on the backside of the fortress, Enoilteca, that offers beautiful views of the Tuscan sunset, as well as a system to try numerous wines from the area.
You can read my full review on our multiple stays at Palazzo Carletti in Montepulciano here. This medieval building was turned into a 18th century palazzo and is a short walk from the main piazza in Montepulciano. If you’re looking to stay in the middle of town, it is my pick. If you’re looking for somewhere outside of Montepulciano, Lupaia is on my list of boutique hotels in Tuscany to try!
Check out my Montepulciano Travel Guide!
Best Gelato (& Cheese) in the Italian Hill Towns
EAT & DRINK: Buon Gusto Gelateria, at least once a day!
EAT & DRINK: Poderuccio for homemade pici
DON’T MISS: Tasting pecorino cheese in Pienza
I couldn’t decide how to organize this post, so I am going to essentially follow one of the drives from this Hill Town travel guide. (More resources below!)
Pienza is a short (beautiful) drive from Montepulciano. (Trust me, I know… we make it daily for gelato.) It is one of the easiest hill towns in Italy to navigate on foot because it’s mostly flat. (If you have trouble walking or don’t enjoy hills, you won’t enjoy Cortona or Montepulciano.) Despite it’s flatness, Pienza offers some beautiful views of the Italian countryside off the back of the cathedral though. It’s one of Tom’s favorite places to take in the view. He isn’t wrong – even in December – the rolling hills outside of Pienza are breathtaking.
There are a lot of souvenir shops in Pienza, so it can be difficult to find some of the authentic experiences offered by other hill towns. That said, we have really enjoyed tasting (and purchasing) cheese from Tavenra del Pecorino. While we typically purchase cheese to enjoy on our trip, they have also vacuum-sealed cheese for us to take home to the US as well.I think Pienza would offer a quieter stay than Montepulciano or Cortona. We’ve been to Pienza in the evenings, and it is very, very quiet. If you are trying to decide where to stay, La Bandita is on my Tuscany hotel list.
There appear to be a number of highly rated restaurants and agriturismos in and around Pienza, but we have not been able to try all of them yet. We’ve learned that reservations are a must, even in December. My best advice? If there’s somewhere you really want to try, make reservations in advance.
Visiting Tuscany for Wine
EAT & DRINK: Caffe Sant’Angelo, particularly for lunch between winery visits
We’ve only visited in the off season, so our full verdict is still out on Montalcino. Of course, given that it’s most famous for its wine, it’s the perfect hill town for wine lovers. There are a lot of enotecas (wine bars) lining the streets of Montalcino. Many offer outdoor seating, even in December. There’s a fortress to appease your husband (or my husband), too. Montalcino is more like Montepulciano and Cortona with its hills – they are steep!
We finished our visit near sunset and the drive back to Montepulciano was absolutely breathtaking. There are a lot of iconic Tuscan views along that drive, so plan to stop and take photos. (Bring a tripod with you! We like traveling with this inexpensive, lightweight tripod.)
Overall, I’ve found hotels in and around Montalcino to be pretty expensive. I adore the Rosewood Castiglion del Bosco for a splurge though!
One of the Most Medieval Towns in Italy
STAY HERE: La Terrazza sul Campo because who doesn’t want to stay in a 13th century palazzo with a view??
BOOK THIS: Walking Tour of Siena with a Contrada visit
DON’T MISS: Piccolomini Library in the Duomo
Oh Siena. You captured my heart in 2004 and we’ve been friends ever since. If Florence is the Renaissance city, Siena is the medieval city of Tuscany. Did you know the entirety of historical Siena is a UNESCO World Heritage site? That alone might mean this perfectly preserved medieval town is worth visiting. You could fill an entire Italy itinerary with UNESCO World Heritage sites I love the architecture, the views from the city walls, and I especially love the passeggiata around the Campo in evenings.
I think you should spend at least one night in Siena, and I stand by the recommendation. If you can’t stay the night, however, Andrea has fantastic guide for making a Rome to Siena day trip. She and I share the same advice: Make sure you see the Siena Duomo. That being said, don’t miss visiting the Piccolomini Library within the Duomo. Believe it or not, I overlooked it on three trips to Siena. Now, it’s one of my favorite things. You’ve never seen frescos like this.
After more than a few misses on meals, I’m definitely booking this Siena food tour for our next trip. I can’t recommend taking food tours when traveling enough. We’ve found so many local products to try and bring home as souvenirs from food tours!
Check out my Siena Travel Guide!
For the Best Scenery in Tuscany
Like Montalcino, we only visited Volterra in December. It was pretty closed up, so I don’t think we got a good feel for everything it had to offer. People were out and about, and the passeggiata and apertivo culture did seem to be alive and well though.
Like Montalcino, Cortona, and Montepulciano, the hills are steep, but the views are incredible. We were in Volterra near sunset and it felt as if we were in a Renaissance painting. My friend Grace visited Volterra in the spring and she refers to it as “everything.” I don’t think she’s wrong. We definitely felt as if the views were everything.
For Art Galleries & Delicious Italian Souvenirs
San Gimignano, Italy
EAT & DRINK: Olive Oil Tasting Tour in Tuscany
San Gimignano is the most pleasant surprise of all the hill towns of Italy. It’s overlooked as a tourist mecca when it has a lot to offer. First, it is a very walkable city. It’s not as flat as Pienza, but it’s not as steep as Montepulciano, Cortona or Montalcino. Tom thinks it has the best views of the rolling hills and olive groves of Tuscany, so its one of his favorites for that reason. Beyond that, I love all the art galleries that are scattered through town. Even in December, it seemed like the town was bustling. (It decorates beautifully for Christmas, too.)
If art isn’t your thing, San Gimignano has the best selection of wines, olive oils and balsamic vinegars to taste in Tuscany. This San Gimignano winery, olive oil, and vinegar tour is one of my favorite things to do when we are in the area. It was a great way to taste many delicious things, and you can book a tasting that includes a traditional Tuscan lunch, too. I’ve never found any of these products in the United States, so if you’re looking for souvenirs to bring home, this is a great idea! They also ship to the US; we ordered a lot of wine to support Italy throughout 2020.
The Most Famous Tower of the Tuscan Hill Towns, Obviously
If Florence is too frantic for your itinerary, Pisa offers just as much bang for your buck at a slower pace. Obviously, you go for the Field of Miracles and the Arno river views. The town is flat and easily walkable. It does get crowded, particularly around the Field of Miracles, but the architecture is beautiful. My favorite experience is to walk from Pisa Centrale to the Field of Miracles. You’ll walk forever and suddenly you turn around, and there’s the Leaning Tower in all its leaning glory. Truly, there is nothing like seeing it in person. I still can’t get over the fact that it really leans.
Since Pisa offers an airport and quite a few low-cost carriers, it’s easy to work in a visit to the Field of Miracles. Just make sure you purchase tickets in advance if you want to climb the tower or see the basilica. You do need to plan ahead for those experiences, even in the off season.
The Flattest Hill Town in Tuscany
Like Volterra, we have only visited Lucca in December. Lucca feels like a tough nut to crack, but if you like being outside, Lucca might be your hill town. We made it halfway around the broad path that runs around (and above) the city walls. The exterior of the cathedral reminds me a lot of the Pisa Duomo, but it’s different and worth seeing. The good thing about Lucca is that it’s a flat hill town, so it’s easily walkable. We visited on a Sunday morning, and it felt very local and very lived in. We even stopped in a cafe for coffee and cookies (and I found my favorite occhi di bue).
Where to Go in Umbria
Most people think that the hill towns of Italy are all in Tuscany. They aren’t! There are some in Umbria, too! Umbria is a new region for us. We started exploring it in April 2018 with two nights in Assisi. In December 2019, we discovered the beautiful Borgo dei Conti and spent our evenings drinking wine and enjoying the Italian hillside. (Don’t miss Volpino for pizza!) I loved Borgo dei Conti so much that we went back for Easter weekend in 2019 and again in June 2021. Like the contrast between Florence and Pisa, you can’t really compare Tuscany and Umbria. Tuscany is busy. It can be more frantic. Umbria is more relaxed. People say it’s more rustic, but I’ve found it to be just as comfortable and accommodating as Tuscany.
For the Best Wine, Truffles & Medieval Walls in Umbria
EAT & DRINK: Enoteca L’alchimista
EAT & DRINK: Olevm
DON’T MISS: Montefalco Wine Tasting
This is a classic walled Italian city and you won’t find it in any US guidebooks. None of the books we use mention it and we can’t understand why not. It’s known for it’s wine and there are a lot of wineries in the area. I highly recommend booking this wine tasting in Montefalco! It’s known for truffles. You can find black or white truffles on the menu depending on the season. It is also known for olive oil. It is also one of the most preserved walled Italian hill towns! And yet, I still can’t figure out why no one mentions it.
We found the whole city to be completely magical, both in the summer, the fall, and at and at Christmas time. At Christmas, it felt a lot like Montepulciano with beautiful squares and magical Christmas lights, but it wasn’t nearly as busy. We had a fabulous meal (with all kinds of truffles) at Olevm. When we returned in summer 2021, we had another delightful dinner on the main square at L’alchimista and spent a lovely morning at the Bocale winery. In both cases, I literally had to push my stomach down the hill when we finished dinner. And – in both cases – we didn’t hear a word of English the entire time we were there.
We certainly had the opportunity to practice our Italian. Montefalco is the perfect combination of rustic sophistication. It’s on our list to return to for a couple of nights. Palazzo Bontadosi is on my list because of its incredible location.
One of the Most Spiritual Towns in Umbria
STAY HERE: Nun Assisi Relais & Spa
BOOK THIS: Assisi Walking and Basilica Tour
BOOK THIS: Olive Oil and Wine Tasting near Assisi
EAT & DRINK: Pizzeria da Andrea, for pizza al tagilo (by the slice)
EAT & DRINK: Il Baccanale
This beautiful stone town is pure magic. You’ll marvel at how they built any of it, especially when you find out that they had to bring many of the stones in to build it. If you’re on a religious pilgrimage – or want to see the evolution of churches in Italy – Assisi is your place. You will want to see the Basilica of St. Francis, of course, but there are many beautiful churches in Assisi. I recommend spending at least a night or two here because it’s so peaceful. The Nun Relais has a fabulous spa to refresh and revitalize the most weary traveler.
In 2021, we booked a wine and olive oil tasting near Assisi, and it was one of our favorite moments of that particular trip. This takes place at a family winery, and we truly enjoyed getting to know the family, sharing some delicious food and wine, and learning more about both wine and olive oil!
Check out my Assisi Travel Guide!
Listen, Learn & Read More
The hill towns of Italy are best explored on foot. Rick Steves has a number of free audio tours available for download. You can pop in your earphones and explore Siena, Assisi, as well as the Basilica of St. Francis using your own two feet. The further off the beaten path of Tuscany and Umbria you go, the more Italian language skills you might need. I strongly suggest using this Italian phrasebook and CD to learn a little Italian before you go. Duolingo works, too, but I prefer DK. I’ve been using it since 2004! An Italian gave it to me while I was in the post office applying for my passport. I’ve been grateful to him (and the books he sent me) ever since.
Tom and I love using books to plan our trip. It also makes for a fun date night, if we’re looking for something to do. These are a few of our favorite books to plan our trips to Tuscany. If you’re planning on renting a car, I recommend these guides: 25 Great Drives in Tuscany and Umbria, Back Roads in Northern and Central Italy, and Back Roads Italy. The 25 great drives book is the only one I’ve seen that mentions Montefalco. The back roads books are how I found some of my favorite restaurants.
Tom loves the pocket-sized Hill Towns of Umbria & Tuscany guide because of the walking tours and maps. I prefer the 10 Best – Florence and Tuscany and Florence and Tuscany – Day by Day books to research restaurants, hotels, and things to see. Most recently, I purchased the DK Florence and Tuscany book, and I’ve been pleased with how it breaks up Tuscany by region and included some of the lesser known cities. Eventually we come up with a itinerary that covers parts of all of these guidebooks.