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.
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.
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.
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 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
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 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.
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.
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.