How to Spend 3 Days in San Gimignano

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.