Private Tour Siena San Gimignano and Chianti from Cortona

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
8 hours
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Number of Guests
2 - 8 guests
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Language
English, Italian
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Other
Private Experience
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Digital Ticket
Mobile or paper ticket accepted

Discover Tuscany's gems on a private tour from Cortona. Explore Siena's historic streets, taste exquisite Chianti wines, and stroll San Gimignano's medieval towers. An unforgettable day.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting.

After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.


What You Get

Private transportation
All Fees and Taxes
On-board WiFi
WiFi on board

Good To Know

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Specialized infant seats are available

What You’ll Experience

1

Piazza del Campo

Piazza del Campo (or simply Il Campo) is the main square of Siena. Famous for its unique shell shape, it is known worldwide for its beauty and well-preserved architecture. It is also the site of the Palio di Siena, a horse race held twice a year. By ancient tradition, the square and the Palazzo Pubblico do not belong to any contrada.
25 minutesAdmission Ticket Included
2

Duomo di Siena

The Siena Cathedral, or Cattedrale di Santa Maria Assunta, is one of the masterpieces of Italian Gothic architecture. Located in the heart of the city, it stands out for its extraordinary façade of white, dark green, and red marble, as well as its interior rich in artworks. It is undoubtedly one of the most beautiful and most visited cathedrals in Italy.
20 minutesAdmission Ticket Included
3

Monteriggioni

Monteriggioni is a small medieval village in Tuscany, in the province of Siena. It is famous for its spectacular walls, making it one of the best-preserved fortified villages in Italy.
20 minutesAdmission Ticket Free
4

San Gimignano

San Gimignano is a charming medieval village located in Tuscany, in the province of Siena. It is famous for its medieval towers, which have earned it the nickname "Manhattan of the Middle Ages". The medieval towers: There were once over 70, today 14 remain, making the village unique in the word. They were symbols of power of the noble families. UNESCO Heritage: The historic center of San Gimignano was declared a World Heritage Site by UNESCO in 1990. San Gimignano is an unmissable destination for those visiting Tuscany, perfect for immersing yourself in the medieval atmosphere and enjoying breathtaking views.
50 minutesAdmission Ticket Free

Meeting & Pickup

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We can pick up guests at any location

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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from  $428.53 
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Please note: The price varies based on group size. The time is in Central European Time.
Free cancellation (24 hours notice)
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INSTANT CONFIRMATION
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Earliest available date: July 12, 2025
from  $428.53  per guest
Book Now
Please note: The price varies based on group size. The time is in Central European Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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