Last Updated on 05/23/2021
Tuscany is the perfect place to visit for the first time traveler in Italy, but it’s also a region you could return again and again. Tuscany is full of countless hilltop towns, each one different yet the same. No matter where you go, you’re sure to find stunning views of rolling hills, exceptional wine, a lively piazza, gelato shops and quaint alleys. Assuredly, you’ll eat pasta that will change your perception of Italian food. While you’re sure to fall in love with this region, these are the top towns in Tuscany you can’t miss on your trip to Italy. I’ve also included a few of the best hotel choices and restaurants in the area.
Montepulciano
During the time we lived in Italy, I went to Montepulicano three times and each time I discovered something different. We always stopped at Caffé Poliziano for breakfast and coffee (or an affogato in the hot afternoon). During Christmas, there’s a festive market and a huge Christmas tree in the main piazza. All year round you can enjoy views of the Tuscan hills and world famous wine.
Stay: Lupaia is a historic villa dating back to 1622 about 10 minutes outside Montepulciano. Rooms and suites are beautifully decorated, each having a private entrance and access to the outdoor oasis.
Pienza
I’m not exaggerating when I say the streets of Pienza smell like pecorino cheese. Seriously. Stop at Marusco e Maria for a wide selection of regional cheeses, spices and wine. Bar Il Casello is the perfect place to grab a glass of wine and relax at the bistro tables facing the Tuscan hillside. I’d recommend going to Pienza in early summer or fall, but for a view of the region in the off season read my post on winter in Tuscany.
Stay: Owned by former Sony music executive who opted for a change of scenery and lifestyle, La Bandita Townhouse is a boutique hotel right in the Pienza center. Hotel San Gregorio on the outskirts of town offers traditional rooms and a convenient underground parking garage.
Monticchiello
My sole purpose for visiting Monticchiello was to have dinner at Osteria la Porta. I tried to visit in January when I was passing though from Venice, but they aren’t open 7 days a week in winter. I was determined to eat there the next time I was in the area. We finally made it in early summer. The owner Daria was so thoughtful and even remembered my failed attempt to reserve a table in winter. The views and the food were equally incredible. Be sure to make a reservation. Thank me later.
Update March 2019: Daria no longer owns Osteria la Porta, but you can still find her and her wonderful food at Ristortante Daria a few doors down. Osteria la Porta is still open as well if you had your heart set on a view.
Lucca
Lucca is known for its city walls that now serve as a pedestrian strolling path. You know Italians are fond of a good evening stroll, known as the passeggiata. This is the place to do it in Lucca. The northwestern Tuscan city is also the place to visit towers and have a local dish of cornmeal, beans and spinach called farinata.
Also Read: A Quick Guide to Lucca, Tuscany
Cortona
My memories from Cortona are filled with stunning views, lively cobblestoned alleys and friendly locals. Home to author of Under the Tuscany Sun, Frances Mayes, you could say Cortona is the embodiment of quintessential Tuscany.
Stay: Villa di Piazzano is a “Small Luxury Hotel of the World” just outside Cortona. A family friend has a villa nearby and absolutely raves about the high quality hospitality and location. For a mid-range option, check out Borgo Il Melone with comfortable rooms and pool.
Also Read: The Perfect Day in Cortona
San Gimignano
San Gimignano is best known for its medieval towers and the best gelato in the world. Try their award winning, inventive flavors like cream with saffron and pine nuts or pink grapefruit with sparkling wine at Gelateria Dondoli. Prepare yourself to wait in line!
Stay: About a 25 minute drive from San Gimignano, you’ll find the luxurious Borgo Pignano. With a pool, stunning views, spa, cooking classes, restaurant and a number of experiences, you won’t want to leave. Plus, they are committed to sustainability. Choose between rooms, suites, spacious marionettes and private villas depending on your needs.
Siena
I think of Siena as the younger, rebellious redhead sister to Florence, the popular cheerleader type. Maybe that’s because Siena can often be overlooked, but mostly because it’s a city full of red brick buildings. There might not be as many famous museums in Siena as Florence, but it’s still a worthy stop in Tuscany. Have a caffé and pastry at Bar Pasticceria Nannini or Gastronomia Morbidi in the morning. Piazza del Campo is the place to be in the evening to people watch and have an aperitivo.
Florence
Can a list of “Top Tuscany Towns” omit Florence? While it’s not really a “town,” I’m not about to. From world famous museums, stunning architecture and piazzas, amazing food, trendy coffee shops and cocktail lounges, Florence is a must do when visiting Tuscany. Also read my full guide to Florence.
Stay: Located right in Piazza Santo Spirito, you can’t miss the Loggia roof bar. You can also book a night at its Hotel Palazzo Guadagni.
For something more in the country, consider Villa Medicea di Lilliano. This property is the perfect choice for a countryside escape while still being just a 20 minute drive from Florence. Choose from a number of different accommodations like spacious suites or small villas with a full kitchen and living space.
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Hilery says
Loving your posts! Super helpful as I’m playing a trip this summer from Florence down to Positano and Capri. Any recommendations for a one-night stay during our drive from Cortona to Naples? We’ve spent time in Rome, so was looking for something a little different. Traveling with 2 older kids (17/20). Thanks so much!
Scarlett | Petite Suitcase says
Might want to look into Orvieto, Viterbo or Sperlonga. Enjoy your trip!
Michelle Stewart says
I stumbled upon your fabulous blog when I googled transportation options to Positano and I’m so grateful for finding it! Planning my 15 year anniversary/bucket list Italy trip for late April/early May and quickly realizing it will have to be part 1 of 3 or 4 because there’s just too much to see and not enough time this go. We’re flying in/out of Rome and want to do a few days in wine country, 2 days in Amalfi and 2/3 days in Rome. Debating between Umbria and Tuscany as simply going into Umbria would be closer to Rome/Amalfi, but obviously Tuscany is what we’re more aware of. We plan on spending some time in Orvieto. Thoughts on other parts of Umbria? Or we should just spend the little extra time and go into Tuscany. Can you hire car tours like in CA wine country? I’m apprehensive to rent a car/drive as we want to do wine tasting and not worry about navigating unfamiliar territory that is already challenging on a good day. We’ll have a Saturday afternoon, Sunday and Monday to explore. Returning to meet friends on Tuesday in Rome to head to Amalfi. Want to see as much as possible but not be too crazy so we can also just enjoy. Thanks so much!
Scarlett | Petite Suitcase says
Hi Michelle,
I completely understand! I lived there for a few YEARS and still did not see all I want to see.
I have been to Orvieto a few times and it is very lovely with a similar feel to hilltop towns in Tuscany. Southern Tuscany (my favorite part) is not too much further than Orvieto. You can look into booking a wine tour on a tour website like TripAdvisor or Viator, but also your hotel is a wonderful resource to help you book a tour. You will need to make a reservation at each winery. It is not like Napa where you can show up at anytime.
Honestly, the whole country of Italy is “wine country” from top to bottom. There are amazing wineries everywhere.
Happy Anniversary and you’ll have to return for the 16th, 17th…
Tory Trocchia says
Scarlett,
Thank you for making this post! I found it on Pinterest while planning my 2-week Italian honeymoon, and I couldn’t be happier that I did, because it led me to your blog which has incredibly informative posts about literally everywhere we are going during our trip – not to mention your breathtaking fine art photos that make everywhere look sooooo dreamy!!! I am planning to use (well really, I already have used) you and your blog as my definitive Italy planning guide. So again, THANK YOU for your incredible organization, curation and recommendations! You rock!
Scarlett | Petite Suitcase says
Wow, Tory! Talk about the most glowing review ever. Thank you! I’m so glad my blog has helped you. I hope you have a wonderful honeymoon that you’ll remember forever. Congratulations!
Devyn says
Thank you for the tips! My husband and I are planning 3-4 nights in Tuscany and are having a hard time deciding if we should make Florence our home base and visit different tuscan towns or to just stay in a tuscan town and do a day trip to Florence. What would you recommend? Would it be helpful to rent a car? We will be coming from Cinque Terre area – what would be the logistics of that?
Thanks!
Scarlett | Petite Suitcase says
Hi Devyn,
There are frequent trains leaving from La Spezia to Florence every day. I think your home base decision depends on what kind of vacation you are looking for… Do you see yourself spending time at a villa in the countryside with a pool? Or maybe a hotel in a smaller Tuscan town? Or do you want to be in a city filled with lots of options for dining, shopping and museums? It is helpful to have a car if you want to see multiple towns each day, but be sure to work out parking with your accommodation if you decide to stay in Florence.
ROMICA RAINA says
i HAVE 5 TP 6 DAYS IN TUSCANY REGION . ..travel in july…where can i stay ..my kids have to travel from Amalfi , to a meeting point in tuscany where we start our travels …where to saty to get the feel of the country side?
Scarlett | Petite Suitcase says
Hello Romica,
Florence would probably be a great meeting point because your kids can easily take the train up from Naples. All of these towns I’ve mentioned in this post are wonderful. Val d’Orcia is one of my favorite areas of Tuscany to enjoy the countryside.
Lauren says
Amazing! Would you say to have a home base and then do trips or just one area if you had 3-4 days?
Scarlett | Petite Suitcase says
I think that’s a great plan, Lauren! You could also 2 and 2 depending on where you are traveling to/from!
Linnea says
Wow! Sienna looks beautiful! I’ve only been to Florence once now you’ve convinced me to branch out!
Scarlett | Petite Suitcase says
Siena is always overlooked! It’s definitely worth a visit!
Joan Diluigi says
Dear scarlett,
I’ve been reading your blogs and I am so interested in all the lovely suggestions that you post .
My grandmother came to America from Grattaminarda, and my grandfather from Bonito .
Can you recommend a way to get some of the family records etc .
I know that my grandfather’s father had a family farm in Bonito . Family name :
Martone .
Scarlett | Petite Suitcase says
Hello Joan,
Unfortunately, I don’t have any recommendations in this department. Ancestry .com maybe? Best of luck in your search!
Arunima Dey says
So beautiful! And lovely post!
Scarlett | Petite Suitcase says
Thank you, Aruniuma!
Teresa / Sunday Spritz says
I feel like you captured the essence of Tuscany perfectly <3
Scarlett | Petite Suitcase says
Aaahhh thank you, Teresa! It’s one of my favorite places!