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How to Spend 3 Days in San Gimignano

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.

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6 Tours and Activities

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San Gimignano Vineyard Dinner and Wine tasting

San Gimignano Vineyard Dinner and Wine tasting

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Enjoy a celebratory evening in Tuscany with a four-course dinner and wine tasting at the atmospheric Torciano Wines Private Reserve. Stroll around the property while admiring the vineyard-draped hills and olive groves, then snack on an appetizer of Tuscan cheeses, salami and Bruschetta. Eat a delicious dinner of truffle lasagna, Tuscan ribollita, roasted meat, and roasted potatoes. Then, enjoy dessert and a tasting of select current and vintage reserve wines.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$187.67
From
$187.67

Fiat 500 Tour of the Chianti Roads from San Gimignano

Fiat 500 Tour of the Chianti Roads from San Gimignano

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Bus tours can make many stops in a short amount of time, but they can be plodding affairs and leave travelers feeling out of touch with the landscapes they drive through. This tour—which takes to the roads of the Chianti region on vintage Fiat 500s—allows visitors more fun and the chance to drive themselves while they follow a guide. Pass medieval villages, rolling countryside, and wineries, and stop for a Tuscan lunch and wine tasting.
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  • 7 hours 30 minutes
  • Free Cancellation
From
$177.05
From
$177.05

Wine, Extra Virgin Olive Oils & Cheese Tasting

Wine, Extra Virgin Olive Oils & Cheese Tasting

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San Gimignano, with its rural, hillside atmosphere, is a great place to sample Tuscan food and wine. This tour pairs Tuscan wine tasting with an elaborate Truffle-based meal at a family-run olive farm and vineyard. The meal is led by one of the farmers, who explains the characteristics of the wines and their organic production. The farm is within walking distance from the center of San Gimignano, so you can walk right over.
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  • 45 minutes
  • Free Cancellation
From
$30.04
From
$30.04

Wine & Evo Oils Tasting with Vegetarian Meal-Private Experience

Wine & Evo Oils Tasting with Vegetarian Meal-Private Experience

Explore Tuscany beyond the center of San Gimignano with this vineyard visit. Travel to a family-run organic farm where grapes and olives are grown. Sample the vineyard’s wines and extra virgin olive oil alongside a vegetarian meal including bruschetta, pasta with vegetables, and a selection of pecorino cheeses. A traditional dessert and dessert wine are included.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$56.66
From
$56.66

Private Wine and Extra Virgin Olive Oil Tasting

Private Wine and Extra Virgin Olive Oil Tasting

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Tuscany is one of Italy’s most famous wine regions, but you don’t need a full day exploring the vineyards to enjoy a taste of Tuscan wine. The family-run Podere la Marronaia winery is just minutes from San Gimignano and this private 45-minute tour includes a tasting of organic wines and extra virgin olive oils.
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  • 45 minutes
  • Free Cancellation
From
$17.70
From
$17.70

Truffle Adventure Cooking Class

Truffle Adventure Cooking Class

Want to have an Elite Experience? Truffle is one of the rarest and delicious products of the world. Italy is one of the main exporters of truffles. Tuscany is one of the most popular Italian regions where to find truffles. Is for all this reason that we decided to give importance to this typical product, entrusting it with a place of honor.
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  • 3 hours
  • Free Cancellation
From
$234.22
From
$234.22