Private Tour Siena San Gimignano and Chianti from Cortona

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Private Tour Siena San Gimignano and Chianti from Cortona

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 US$405.23  per guest
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Adult x1
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Available Today
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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
1 - 8 guests
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Accessibility
Stroller Accessible
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Language
English, Italian
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Other
Family-friendly, 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
On-board WiFi
WiFi on board
Bottled water

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 Not Included

Monteriggioni (Pass By)

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.
3

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

Pickup Point
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Pickup Details
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.

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Reviews
5.0
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based on 5 reviews
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(TripAdvisor)
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One of the best days of my life
June 20, 2026

This was seriously the most amazing experience of my entire life Max was the funnest, funniest and coolest guide. He was so knowledgeable, so attentive so caring and so positive. I will use this co...read more

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(TripAdvisor)
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From Texas to Tuscany
September 03, 2025

Max was great and helped us so much to navigate through with precise directions and enough time to enjoy a few different cities. He was such a great guide for our first time in Italy Would recomme...read more

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(TripAdvisor)
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Wonderful trip and service!
June 12, 2025

Amazing trip with Luca. Made the trip memorable for our family of 4 and still managed to fit in a bit of time a local winery! Loved both San Gimignano and Monteriggioni and really enjoyed Luca’s ...read more

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(TripAdvisor)
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Luca – The Heart and Soul of Italian Travel
June 08, 2025

Luca provided outstanding customer service throughout the entire tour. He was patient professional and explained contextualized historical information so that we understood the importance of what w...read more

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(TripAdvisor)
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Wonderful experience!
June 04, 2025

Luka was wonderful! The time allocation accross each of the three places was exactly right. It was entertaining and also relaxing. We didn’t feel rushed or overwhelmed and had time to explore. I hi...read more

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