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Top Ten Places to Go in Tuscany

Hill Towns and Travel Attractions in Tuscany

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Tuscany, with its spectacular hill towns and scenery, is one of Italy's top vacation destinations. Tuscany's travel attractions include historic cities and art, great wine and food, medieval hill towns, beaches, and beautiful countryside.

1. Florence

florence picture, ponte vecchio, tuscany picture
Florence Picture: Ponte Vecchio by Martha Bakerjian

Florence is one of the most important Renaissance architectural and art centers. Its Duomo and Baptistery are magnificent but crowded with tourists as is their large piazza. Florence has several interesting museums with many famous paintings and sculptures. There are also Medici palaces and gardens.

Florence Photo Galleries | Top Rated Hotels

2. Siena

siena picture, piazza del campo siena, tuscany picture
Siena Picture: Piazza del Campo by James Martin

Siena is a classic medieval hill town in Tuscany famous for its large fan-shaped piazza, Piazza del Campo, and summer horse-race, known as Il Palio. Siena's tall bell tower, Torre del Mangia, dominates the Piazza del Campo. Siena offers other good tourist sites including its cathedral and museums.

Siena Pictures | Top Rated Siena Hotels

3. Pisa

Photo of Pisa's Baptistery, tuscany picture, pisa picture
Tuscany Picture: Pisa's Baptistery by James Martin

Pisa, in northern Tuscany, is famous for its leaning tower but Pisa has much more to offer the traveler, including its medieval center, beautiful Duomo and Baptistery, parks, statues, the homes of Lord Byron and Shelley, and a walk along the river.

Pisa Pictures | Top Pisa Hotels

4. Lucca

lucca picture, guinigi tower
Tuscany Picture: Lucca by Martha Bakerjian

Lucca is a walled city with one of the best-preserved walls in Italy. Atop the walls are walking and bicycling paths and gardens, allowing you to walk completely around Lucca's historic center. Lucca has several well-preserved towers from where you can get fabulous views of the city by climbing to the top. Lucca is a good city for food shopping and restaurants.

Lucca Photos from the Giunigi Tower | Lucca Hotels

5. Cortona

cortona picture
Tuscany Picture: View from Cortona by James Martin

Cortona is the Tuscan hill town made famous by Francis Mayes in her book Under the Tuscan Sun. Cortona is surrounded by Etruscan walls, around 3000 years old, and retains much of its history through its architecture, layers of history built upon the Etruscan core. Cortona has stately buildings, interesting medieval architecture, beautiful views, and a large ex-pat community so you'll find lots of English spoken.

Cortona Pictures | Top Rated Cortona Hotels

6. San Gimignano

san gimignano picture, san gimignano towers, tuscany picture
Tuscany Picture: San Gimignano by James Martin

San Gimignano, known as the City of Beautiful Towers, is a classic medieval walled hill town in Tuscany, famous for its 14 surviving medieval towers creating a beautiful skyline visible from the surrounding countryside. Near San Gimignano you can also visit Volterra, an interesting hill town that sees fewer tourists.

San Gimignano Pictures | Where to Stay in San Gimignano

7. Chianti Classico Wine Region

chianti winery picture
Chianti Wine Tasting by James Martin

The Chianti Classico wine region lies between the larger cities of Florence and Siena and is a very interesting region to visit. The Chianti region has picturesque villages, wineries, and beautiful countryside. A good place to start your wine tasting is at Barone Ricasoli Winery and Brolio Castle.

Winery Guided Tours | Where to Stay in the Chianti Wine Region

8. Montepulciano

montepulicano pictures, montepulciano main square picture
Montepulciano Picture © by Barbara Molini

Montepulciano is a walled city in Tuscany, built on a sloping and narrow limestone ridge. Montepulciano, known for the wine called Vino Nobile, has one of the most impressive main squares in Tuscany and has many beautiful Renaissance buildings. Nearby is Montalcino, known for its great wine, with a castle at the edge of the town that has wine tasting.

Montepulciano Pictures | Winery Guided Tours

9. Pienza and Val D'Orcia

val d'orcia pictures, tuscany pictures, pienza pictures
Val d'Orcia Pictures © 2008, Joe Palisi

Pienza, designed to be the ideal city, is a pretty Renaissance town in the Val D'Orcia of Tuscany. Pienza is famous for its pecorino cheese, Piccolomini Palace, and balcony overlooking the beautiful Val D'Orcia, a UNESCO World Heritage Site.

Val D'Orcia Pictures

10. Montecatini Terme

montecatini funicular photo
© by James Martin

Montecatini Terme, known for its thermal waters, is one of Italy's top spa towns. It has several historic spas and spas with modern equipment for beauty and wellness treatments. Terme Tettuccio is a lavish classic spa with music performances daily during the season, worth a visit just to see the Liberty style architecture. The town itself is pleasant and relaxed and makes a good base for visiting central Tuscany. A historic funicular railway (shown in the photo) takes visitors up the hill to the old town of Montecatini Alto.

Montecatini Alto Pictures | Top Rated Montecatini Terme Hotels

Tuscany Off the Tourist Track

Here are my suggestions for places to go in Tuscany away from the tourist crowds but that still have interesting sights.
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