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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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14 Tours and Activities | All San Gimignano Tours

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Wine Tasting & Tuscany Countryside including San Gimignano & Volterra

Wine Tasting & Tuscany Countryside including San Gimignano & Volterra

star-5
See a different side of Tuscany on this full-day, small-group tour. Meet your tour guide at a central point to travel via air-conditioned vehicle into the Tuscan countryside. Visit the ancient town of Volterra, renowned for its Etruscan history and Roman–era ruins. Then, stop at a local winery to enjoy a traditional Tuscan lunch and numerous wine samples. Finally, head to the UNESCO-listed city of San Gimignano, which is famed for its soaring towers.
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  • 9 hours
  • Free Cancellation
  • Taking safety measures
From
$171.73
From
$171.73
Taking safety measures

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

star-4.5
Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$36.16
From
$36.16
Taking safety measures

Romantic Vineyard Dinner Experience in Tuscany

Romantic Vineyard Dinner Experience in Tuscany

star-4.5
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
$185.62
From
$185.62

Private Walking Tour: San Gimignano and its Towers

Private Walking Tour: San Gimignano and its Towers

Discover San Gimignano with your own private guide. During a 2-hour walking tour, you’ll explore the famous Tuscan hill town, which is designated as a UNESCO World Heritage Site. Hear the history behind landmarks such as the Torre Grossa and the Collegiate Church of Santa Maria Assunta, and see the city walls and ruins of a 16th-century fortress.
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  • 2 hours
  • Free Cancellation
From
$196.27
per group
From
$196.27
per group

Full-Day Chianti Tour by Vespa Scooter

Full-Day Chianti Tour by Vespa Scooter

star-3.5
Hop on a scooter to explore the rolling landscapes of Chianti on this 7.5-hour Vespa tour from San Gimignano. Settle on a Vespa and ride around vine-coated hills, cypress groves and old villages, soaking in the views of this famous wine producing region. Your tour includes a wine tasting and lunch, plus the option to ride as a passenger with an escort driver or to upgrade to drive your Vespa.
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  • 7 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$155.49
From
$155.49
Taking safety measures

Fiat 500 Tour of the Chianti Roads from San Gimignano

Fiat 500 Tour of the Chianti Roads from San Gimignano

star-5
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
  • Taking safety measures
From
$180.80
From
$180.80
Taking safety measures

Wine & Evo oil tasting with Truffle Meal

Wine & Evo oil tasting with Truffle Meal

star-4
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
$55.45
From
$55.45

Romantic Candlelight Dinner and Wine in Tuscany

Romantic Candlelight Dinner and Wine in Tuscany

star-5
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
$125.36
From
$125.36

Family-Friendly Cooking Class - Food and Drinks included

Family-Friendly Cooking Class - Food and Drinks included

Young chefs-in-the-making can try their hand at cooking delicious Italian foods. Learn the secrets of making an authentic meal, from starters to handmade pasta to dessert, with the assistance of a professional chef. Children teens, and adults alike enjoy this hands-on cooking class in San Gimignano.
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  • 3 hours
  • Free Cancellation
From
$119.73
From
$119.73

Wine Tasting Montalcino and Fiorentina Dinner

Wine Tasting Montalcino and Fiorentina Dinner

star-5
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
$108.48
From
$108.48

Private Pasta and Ice Cream Cooking Class - Food and Drinks included

Private Pasta and Ice Cream Cooking Class - Food and Drinks included

Few dishes are as emblematic of Italian cuisine as pasta and ice cream, so get a hands-on introduction to preparing them with this private, small-group Tuscan cooking class. Your personal chef will walk you through the process, helping you whip up three different pasta dishes and some authentic ice cream. Enjoy with Tuscan wines.
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  • 3 hours
  • Free Cancellation
From
$98.14
From
$98.14

Private Pizza Cooking Class - Food and Drinks included

Private Pizza Cooking Class - Food and Drinks included

Savor the scents and flavors of Tuscany on this pizza-cooking class near San Gimignano. Choose an afternoon or evening class, and learn the art of selecting ingredients according to region and season. Prepare your dough with tips from your instructor, and fling your base like a real Italian ‘pizzaiolo’—or pizza chef. When your tasty pizza comes out of the oven, savor your meal with local Tuscan wine and oils.
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  • 3 hours
  • Free Cancellation
From
$85.87
From
$85.87

Wine & Evo Oils Tasting with Vegetarian Meal

Wine & Evo Oils Tasting with Vegetarian Meal

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
  • Taking safety measures
From
$55.45
From
$55.45
Taking safety measures

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
$235.04
From
$235.04