San Gimignano Travelers Recommend

Discover perfectly preserved medieval villages and captivating landscapes by taking two days to explore the historic center of San Gimignano and surrounding wine country plus the delightful town of Siena, Volterra, or Montalcino. Here are your best options for pairing striking cityscapes with scenic Tuscan countryside in two days.  

Day 1: The Towers of San Gimignano

**Morning:**Begin first thing in the morning by getting to know San Gimignano’s delightful medieval center, a UNESCO World Heritage Site, on a walking tour. Learn about the history of its 14 towers, and visit highlights such as the Large Tower (Torre Grossa), Collegiate Church of Santa Maria Assunta, Cathedral Square (Piazza Duomo) and Cistern Square (Piazza della Cisterna), and ruins of the 16th-century fortress.

**Afternoon:**San Gimignano is surrounded by some of the loveliest landscapes and most prestigious wine country in Tuscany. Tour the countryside by Fiat 500 car or Vespa scooter or with a more traditional wine tour stopping at nearby wineries. Foodies can join a truffle hunt and cooking class or a lesson in preparing pasta, pizza, or gelato followed by a convivial dinner.

**Night:**In addition to excellent wine, traditional Tuscan food is at the heart of San Gimignano. Be sure to sample some of the most beloved local dishes over a romantic candlelight dinner in town or in a winery in the surrounding hills. Sample cheeses and charcuterie,ribollita (Tuscan bread soup), truffles, and area wines. 

Day 2: Tuscany’s Hill Towns

**Morning:**Set your sights farther afield today and explore the hill town of Siena, home to a UNESCO-listed historic center, exquisite Gothic cathedral, and the rolicking Palio festival. Beat the crowds by booking skip-the-line tickets to the cathedral (duomo) complex so you have plenty of time to explore the cathedral, crypt, baptistry, museum, and Piccolomini Library.  

**Afternoon:**Ancient-history buffs can instead opt to tour Volterra, a former Etruscan stronghold with fascinating archaeological ruins and museum. Explore the historic center on foot to take in the medieval city hall and Via Porta all’Arco, known for its artisan book binderies, leather and bronze workshops, jewelers, and more.

**Night:**True wine aficionados can cap off the day with a jaunt to Montalcino to sample its prestigious Brunello di Montalcino, one of the most popular Italian varietals. This area of Tuscany is known for its Fiorentina, an impressively thick steak cooked over wood coals and the perfect foil to the bold local red.

Soaring high above the medieval center of San Gimignano, the town’s 14 towers form one of the most remarkable skylines in Tuscany. This UNESCO World Heritage Site hill town is beloved for its intact historic center, excellent food and wine, and endless views over the pastoral countryside. Here’s how to experience its singular appeal in just one day.

Morning: Historic Center

The compact historic center of San Gimignano is considered one of the most enchanting in Tuscany, with medieval streetscapes virtually frozen in time since the town’s 14th-century heyday and more than a dozen of its original 72 towers still standing. Join a small-group or private walking tour to appreciate gems such as the Large Tower (Torre Grossa) and the Collegiate Church of Santa Maria Assunta. Stroll through Cathedral Square (Piazza Duomo) and Cistern Square (Piazza della Cisterna), take in the medieval city walls, and explore the ruins of the 16th-century fortress while learning about the rise and fall of this town along the ancient Via Francigena.

Afternoon: The Wine Country

One of the biggest draws of San Gimignano is its captivating setting deep in the Tuscan hills, surrounded by some of the region’s most prestigious wine country. Set off in the afternoon to explore the countryside and sample wine at nearby wineries. For a lighthearted twist, you can tour the vineyard-covered hills by Italy’s iconic Fiat 500 car or Vespa scooter. Dedicated gourmands can also opt for a cooking class or truffle hunt followed by a cooking lesson to learn how to prepare Tuscan classics and enjoy the results during a celebratory dinner. Alternatively, head farther afield in the afternoon to visit the historic town of Siena, home to the famed Palio, or Volterra, with its fascinating Etruscan history.

Night: The Flavors of Tuscany

Cap off your day in San Gimignano by sampling local specialties during a romantic candlelight dinner in the historic center or in a scenic winery outside of town. Enjoy artisan cheeses and charcuterie from the region, traditional Tuscan dishes such as ribollita (Tuscan bread soup) and truffle pasta, and local wines paired with each course. Whether you choose to dine in town or in the countryside, be sure to catch the sunset over the rolling landscape at dusk, when the golden light creates a postcard-perfect view.

More than just the quintessential Tuscan village, San Gimignano is also the ideal base for exploring the pastoral countrysides and gem-like towns of Chianti, the Val d’Orcia, and the Crete Senesi. Here’s how to take in San Gimignano and the surrounding vineyards, olive groves, and villages in three days.

Day 1: San Gimignano

Savor the time-capsule atmosphere of San Gimignano today, and explore the town’s delights inside and outside the medieval city walls. On a morning walking tour, explore the historic center, a UNESCO World Heritage Site, taking in its 14 soaring towers, Collegiate Church of Santa Maria Assunta, Piazza Duomo, Piazza della Cisterna, and the remains of the town’s 16th-century fortress. In the afternoon, set off to explore the surrounding Chianti hills by Fiat 500 car or Vespa scooter, or join a wine tour to taste local labels at scenic hillside wineries. Hands-on foodies can learn how to re-create classic Tuscan dishes during a cooking class or truffle hunt followed by a cooking lesson.

Day 2: Siena, the Crete Senesi, and the Val d’Orcia

On your second day, head to Siena’s historic center to take in its architectural masterpieces and views across the undulating Crete Senesi and Val d’Orcia. Avoid the tour-bus crowds by beginning with a skip-the-line tour of the city’s exquisite Gothic cathedral, home to works by Donatello, Michelangelo, and Bernini, as well as the cathedral’s crypt, baptistry, museum, and Piccolomini Library. Afterwards, get to know the medieval center with a tour of the Piazza del Campo, Palazzo Pubblico, Torre del Mangia, and Basilica di San Domenico. Learn about the Palio festival, one of the most historic celebrations in Italy, and take a stroll through the contrade districts.

Day 3: The History and Workshops of Volterra

Though less famous than Siena, the Tuscan hill town of Volterra is no less storied. If anything, the history of this delightful center not far from San Gimignano stretches even further back than its medieval neighbor, with origins that can be traced to the Etruscans eight centuries before Christ. Ancient-history enthusiasts will enjoy touring the captivating archaeological ruins and museum dedicated to this enigmatic culture, which was later assimilated into the Roman empire. Walking tours also take in the historic center, with its 13th-century Palazzo dei Priori city hall, cathedral decorated with works by Andrea della Robbia and Benozzo Gozzoli, and Roman theater from the first century BC. A highlight is Via Porta all’Arco, lined with artisan workshops turning out paper, leather, bronze, and gold.