The Top 10 Places to Go in Tuscany

Rolling hills of Tuscany outside of Lucca

TripSavvy / Jamie Ditaranto

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

Each part of the Tuscany region has its own unique personality. And while it's hard to narrow down a best-of list in an area of travel superlatives, the following are TripSavvy's top 10 places to visit for medieval and Renaissance architecture, gorgeous scenery, and of course, the food and wine. 

01 of 10

Florence

San Freddiano, Florence, Italy

TripSavvy / Christopher Larson

Florence, in the heart of Tuscany, is one of Italy's top cities to visit. Florence is an important Renaissance architecture and art center with several excellent museums. Florence's cathedral, or Duomo, with its famous dome and its Baptistery, are architectural wonders that are not to be missed.

Many visitors use Florence as their base for winery tours or day trips to other towns in the region. Visit the Museo Galileo or the Palazzo Strozzi to get a feel for the history and culture of the area.

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02 of 10

Siena

View of rooftops in Siena

TripSavvy / Christopher Larson 

Siena is a classic medieval hill town in Tuscany famous for its sizeable fan-shaped piazza, the Piazza del Campo, dominated by its bell tower, the Torre del Mangia. 

Siena's annual summer horse race, Il Palio, is about as different from the Kentucky Derby as one can imagine: Bareback riders race the horses along the city's cobblestone streets, keeping with medieval tradition. 

Siena's medieval streets are lined with shops and rustic trattoria serving traditional Tuscan cuisine off the main piazza. Find a cozy spot, preferably one filled with Italians, and sample local fare paired with a nice bottle of regional wine.

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Pisa

Tower of Pisa and The Duomo

TripSavvy / Jamie Ditaranto 

Pisa, in northern Tuscany, is famous for its leaning tower, which all visitors must climb and take an excellent touristy photo with. You'll be in the Piazza Dei Miracoli, where you can admire the cathedral and the baptistery, which date back to the Italian Renaissance. 

Besides its tower, Pisa has much more to do and see. To visit its historic Piazza Dei Cavalieri, take a stroll along the Arno River. And before you leave Pisa, try the local delicacy, a chickpea flour bread called cecina.

If you visit Pisa in June, you're in for a treat. That's when the city holds a festival to honor its patron saint San Ranieri during its annual Giugno Pisano.

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04 of 10

Lucca

A view of the Lucca skyline from the Guinigi Tower

TripSavvy / Jamie Ditaranto 

Lucca is famous for its Renaissance-era wall, which encircles the city, and its cobblestone streets. Walking and bicycling paths and gardens sit atop the wall, allowing visitors to walk entirely around Lucca's historic center.

In addition to being home to several historic cathedrals, Lucca has several well-preserved towers that provide fabulous views of the city and beyond.

Be sure to check out the home of the famous opera composer Giacomo Puccini, which is a popular museum in Lucca. And for authentic regional dishes like tortelli lucchese or zuppa di farro all lucchese, visit one of Lucca's excellent restaurants, such as Buralli or La Buca di Sant'Antonio.

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Cortona

Cortona, Tuscany, Italy

TripSavvy / Christopher Larson

Cortona is the Tuscan hill town made famous by Francis Mayes in her book "Under the Tuscan Sun." Surrounded by 3,000-year-old Etruscan walls, Cortona retains much of its history through its layers of architecture.

Cortona's stately buildings include the Abbazia Farneta and the Chiesa San Francesco. This area has a large American expatriate community, so tourists from the States will find plenty of English speakers.

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06 of 10

San Gimignano

A view of San Gimignano from a far with a vineyard in the foreground

TripSavvy / Christopher Larson

San Gimignano, known as the City of Beautiful Towers, is a classic medieval walled hill town famous for its 14 surviving medieval towers. These create a distinctive skyline visible from the surrounding countryside. 

Be sure to visit the Museo Estrusco and the historic Collegiata di Santa Maria Assunta. For local flavor, try one of the many cinghiale (wild boar) dishes at Cum Quibus or Ristorante San Martino.

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07 of 10

Chianti Classico Wine Region

Chianti Wine Region, Tuscany, Italy

TripSavvy / Christopher Larson

The Chianti Classico wine region lies between the larger cities of Florence and Siena and is a fascinating area to visit. The Chianti region has picturesque villages like Greve and, of course, many fine wineries. Start your wine tasting at ​Barone Ricasoli Winery and Brolio Castle.

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08 of 10

Montepulciano

Montepulciano, Tuscany, Italy

TripSavvy / Christopher Larson

Montepulciano is yet another walled city in Tuscany, built on a sloping and narrow limestone ridge. Montepulciano has one of the most impressive main squares in Tuscany and has many beautiful Renaissance buildings, including the Chiesa di Sant'Agostino. Visit the Avignonesi or Gattavecchi vineyards or any of Montepulciano's many wineries for a taste of the famed Vino Nobile di Montipulciano. There are also several cantinas in town offering wine tastings and sales and local culinary products.

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09 of 10

Pienza and Val D'Orcia

Vineyards in Val d'Orcia

TripSavvy / Lauren Breedlove

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.

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10 of 10

Montecatini Terme

Montecatini Terme, Tuscany, Italy

TripSavvy / Christopher Larson

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 to see the Liberty-style architecture.

The town itself is pleasant and relaxed and makes a good base for visiting central and northern Tuscany. A historic funicular railway takes visitors up the hill to the old town of Montecatini Alto.


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