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How to Spend 2 Days in San Gimignano

How to Spend 2 Days in San Gimignano

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.

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7 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
$187.71
From
$187.71

Fiat 500 Tour of the Chianti Roads from San Gimignano

Fiat 500 Tour of the Chianti Roads from San Gimignano

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3
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
$177.08
From
$177.08

Wine & Evo oil tasting with Truffle Meal

Wine & Evo oil tasting with Truffle Meal

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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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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$76.74
From
$76.74

San Gimignano Candlelight Romantic Dinner and Wine in Tuscany

San Gimignano Candlelight Romantic Dinner and Wine in Tuscany

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Enjoy a celebratory evening in Tuscany with a romantic dinner and wine tasting. After a relaxing walk around the historic San Gimignano property, settle into a delicious multi-course meal. Sample an appetizer of Tuscan cheeses, salami, and bruschetta before moving on to truffle lasagna, roasted meat, and vegetables, and a dessert of vanilla ice cream with Balsamic vinegar. Take a winery tour and taste current and vintage reserve wines.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$106.25
From
$106.25

Wine Tasting Montalcino and Fiorentina Dinner

Wine Tasting Montalcino and Fiorentina Dinner

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6
Absorb the Tuscan atmosphere and indulge in a wine tasting class and 4-course Tuscan dinner in San Gimignano. Head to Tenuta Torciano Winery and begin sampling some of the vineyard’s best wines accompanied with appetizers and informative commentary from the sommelier. Then sit down to a delicious Tuscan dinner that has been paired with more local wines.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$106.25
From
$106.25

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
$56.67
From
$56.67

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
$234.27
From
$234.27