Top Ten Places to Go in Tuscany

What to do and where to eat and drink in the Tuscan region.

Duomo di Siena
••• Siena, Italy. Miemo Penttinen/miemo.net /Getty Images

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. 

Each part of the Tuscan region has its own unique personality. All are worth a visit for the medieval and Renaissance architecture and of course, the food and wine. 

  • 01 of 10
    Florence, Piazza della Repubblica
    ••• Sylvain Sonnet/Getty Images

    Florence, in the heart of Tuscany, is one of Italy's top cities to visit. Florence is an important Renaissance architectural and art center with several excellent museums. Florence's Cathedral, with its famous dome, and its Baptistery are architectural wonders that will impress even the most jaded tourist. 

    From Florence you can take winery guided tours or day trips to other Tuscan towns. Visit the Museo Galileo or the Palazzo Strozzi to get a feel for the history and culture of the area. 

    Best Florence Hotels on TripAdvisor | Florence Photo Galleries |

  • 02 of 10
    Duomo di Siena
    ••• Miemo Penttinen/miemo.net/Getty Images

    Siena is a classic medieval hill town in Tuscany famous for its large 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, in keeping with medieval tradition. 

    When visiting Siena visitors will want to sample local cuisine like fagioli all'uccelletto. Be sure to pair it with a good bottle of Tuscan wine. 

    Best Siena Hotels on TripAdvisor | Siena Pictures |

  • 03 of 10
    The Baptistery and the Duomo, Piazza dei Miracoli, Pisa, Italy
    ••• Atlantide Phototravel/Getty Images

    Pisa, in northern Tuscany, is famous for its leaning tower, which all visitors must climb and take a good touristy photo with. You'll be in the Pizza dei Miracoli, where you can admire the Cathedral and the Baptistery, both of 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, be sure to 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.

    Best Pisa Hotels on TripAdvisor | Pisa Pictures |

  • 04 of 10
    Restaurants in Piazza Anfiteatro at dusk
    ••• Rachel Lewis/Getty Images

    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, which allows visitors to walk completely 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 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. 

    Best Lucca Hotels on TripAdvisor | Lucca Photos from the Giunigi Tower |

    Continue to 5 of 10 below.
  • 05 of 10
    View from the medieval town of Cortona towards Lago Trasimeno, at sunset, Cortona, Tuscany, Italy, Europe
    ••• Patrick Dieudonne/Getty Images

    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.

    Best Cortona Hotels on TripAdvisor | Cortona Pictures |

  • 06 of 10
    Elevated view of San Gimignano.
    ••• Shaun Egan/Getty Images

    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 dishes at Cum Quibus or Ristorante San Martino.

    Best San Gimignano Hotels on TripAdvisor | San Gimignano Pictures |

  • 07 of 10
    Vineyards in the Chianti Classico region of Italy
    ••• Matthew Hutchinson/Flickr/CC BY 2.0

    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 like Greve, and of course, many fine wineries. Start your wine tasting is at ​Barone Ricasoli Winery and Brolio Castle.

    Best Greve, Chianti Hotels on TripAdvisor | Winery Guided Tours | Top Villages in the Chianti Wine Region |

  • 08 of 10
    Montepulciano during blue hour
    ••• David Pinzer Photography/Getty Images

    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.

    Best Montepulciano Hotels on TripAdvisor | Montepulciano Pictures | Winery Guided Tours |

    Continue to 9 of 10 below.
  • 09 of 10

    Pienza and Val D'Orcia

    Street along town of Pienza, Chianti Region, Siena Province, Tuscany, Italy
    ••• Danita Delimont/Getty Images

    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.

    Best Pienza Hotels on TripAdvisor | Val D'Orcia Pictures |

  • 10 of 10
    Montecatini Terme, Tuscany, Italy
    ••• Andrea Pistolesi/Getty Images

    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 takes visitors up the hill to the old town of Montecatini Alto.

    Best Montecatini Hotels on TripAdvisor | Montecatini Terme Map | 7 Tuscany Spa Towns |

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.