Tuscany is one of those places that captures you from the moment you arrive with its rolling hills, medieval towns, incredible views, and some of the best food in Italy. On our trip through the region, we explored charming villages, historic cities, and unforgettable landscapes, each offering its own special charm. Whether you’re searching for the best things to do or the most delicious things to eat, Tuscany has something for every traveler. This guide highlights the towns we visited, what we loved, and tips to help you plan your own perfect Tuscan adventure.
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Florence
The capital of the Tuscany region and one of the most iconic cities in Italy Florence is easily one of our favorite places to visit. The moment you arrive, you’re surrounded by stunning Renaissance architecture, charming streets, and of course, the breathtaking cathedral that dominates the skyline. You can easily spend a few days here exploring museums, shopping, and trying some of the best things to eat in the region. Restaurants and gelato shops are everywhere, and many of them are absolutely worth a stop.
Things to Do
- Attractions – Duomo, Palazzo Vecchio, Ponte Vecchio, Piazzale Michaelangelo, Basilica of Santa Croce
- Food places – All’antico Vinaio, Da Nerbone, I’tuscani, Panetteria e Stuzzicheria de Nero
- Gelatos – La Strega Nocciola, La Sorbetteria, Gelatteria dei Neri
Siena
A charming medieval town just an hour from Florence, Siena quickly became a standout for us. We spent one night here, which was enough to see the main attractions and enjoy a delicious lunch in the Piazza del Campo. If you prefer a slower pace, two days would be perfect giving you time to try a few restaurants or relax with a drink in the square.
Things to Do
- Attractions – Duomo do Siena, Piazza del Campo, Museum Santa Maria della Scala
- Food places – Pier Pettinaio, Ostaria Permalico, Pretto Prosciutteria
- Gelatos – Venchi Cioccolato e Gelato, Grom, Gelateria La Mandorla
Pienza
Pienza is a beautiful hilltop town south of Siena, famous for its incredible views of the Val d’Orcia. We stopped briefly to walk around, and immediately wished we had stayed longer. The town has several restaurants with postcard-worthy views, making it a wonderful place for a slow afternoon with wine and snacks or even an overnight stay to fully soak in its charm.
Things to Do
- Attractions – Pienza Cathedral, Walk around the town get views of Val d’Orcia
- Food places – Idyllium, Pane Vino & Zucchero, Trattoria la Chiocciola
- Gelatos – Fredo Gelateria, Buon Gusto Gelateria
Montepulciano
We fell in love with Montepulciano, a fortress town surrounded by vineyards and some of the best wineries in Tuscany. We stayed one night, but highly recommend two or three nights if you want to explore nearby wineries, enjoy incredible food, and wander the town’s historic streets.
Things to Do
- Attractions – Sanctuary of the Madonna di San Biagio, Ercolani underground cellar
- Food places – La Schiaccia dell’Opio, Bar Enoteca Piazza delle Erbe, Ristorante La Briciola
- Gelatos – Buongusto Gelateria, Salamoia Gelateria
Monte Riggioni
Just 30 minutes outside Siena is the unique walled town of Monteriggioni. It’s small enough to walk from end to end in minutes, but charming enough to spend a few hours enjoying. Grab a coffee or pastry in the main square and take in the views of the tiny church and surrounding countryside. A short visit is all you need, but it’s well worth the stop.
Things to Do
- Attractions – Piazza Roma, Surrounding scenery
- Food places – Osteria Antico Travaglio, Ristorante Le torri Monteriggioni
San Gimignano
Located just north of Monteriggioni, San Gimignano is another stunning hilltop town known for its medieval towers. We visited for the day, but you can easily spend a night or two. We enjoyed delicious lasagna, had some of the town’s famous gelato, and visited Parco della Rocca for panoramic views of the area.
Things to Do
- Attractions – Duomo di San Gimignano, Parco della Rocca
- Food places – Bar Ristorante Boboli, Forno Moderno
- Gelatos – Gelateria Dondoli
>> Want more Italy travel inspo?? Check out our Best Places to Visit in Italy post! <<
Pisa
Known worldwide for its iconic Leaning Tower, Pisa was a quick stop for us. It’s perfect for a half-day visit or a short detour on the way to Cinque Terre. The Piazza del Duomo, where you’ll find the tower and the cathedral, is absolutely breathtaking in person.
Things to Do
- Attractions – Tower of Pisa, Cattedrale di Pisa, Angelo Caduto
- Food places – L’Ostellino, Bistrot dell’Opera
- Gelatos – Gelato Dipendente, La Bottega del Gelato
Lucca
We only spent one night in Lucca, but immediately felt like it was a place you could stay for two or three nights and simply relax. The town has a magical charm to it almost reminding us of Harry Potter and it’s also a great day trip option from Cinque Terre.
Things to Do
- Attractions – Duomo di San Martino, Guinigi Tower, Piazza dell’Anfiteatro, Torre delle Ore
- Food places – L’Angolo Tondo, Gigi Trattoria, Pinelli Bakery
- Gelatos -I Gelati di Piero, Gelateria La Crema Matta
Tuscany is filled with unforgettable towns, incredible food, and must-see views at every turn. Whether you’re exploring iconic cities like Florence and Siena or wandering through smaller gems like Pienza and San Gimignano, each destination offers its own unique charm. No matter where you go, Tuscany promises beautiful moments, delicious meals, and memories you’ll want to relive again and again.
Did you know: You can book the best activities using our Get Your Guide link, at no additional cost to you! See what excursions you can find for your next trip here.
Disclaimer: All the information shared is based on our research and experiences. Please note that we are not travel consultants, tour guides, or financial advisors and are not held liable for any misinformation. We give suggestions, but advise each person to do their own research and make the decision that best suits them. This blog posts also contains affiliate links, by using the links we provide you are helping us at no additional cost to you.
