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.
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.
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.
Hotel Residence San Gregorio is a nice choice if you want to stay walking distance to the town center. They were one of the few hotels open when I visited in the middle of winter and also offer free underground parking. 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.
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.
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!
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.
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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!
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!