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Exclusive Siena and San Gimignano Tour & Chianti Wine Experience

39 Reviews 4.90 out of 5 stars Based on 39 reviews collected by Key West Private Charters and TripAdvisor |
Recommended by 97% of reviewers
97% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Florence, Italy
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from $142.66 per person

Lowest Price Guarantee
San Gimignano
San Gimignano
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience Image 3
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience Image 4
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience Image 5
Don't miss out!
On average, this is booked 24 (0) days in advance.
10 hours 30 minutes (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany.

The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral.

No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany.

End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture.

A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!

What's Included

  • Expert English Only Tour Leader
  • Free time in San Gimignano
  • Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi
  • Pick up and drop off
  • Gratuities
See 4 moreSee 4 more

Meeting Location

Meeting point

Piazzale Montelungo
50129 Firenze FI, Italy

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Siena

The adventure begins in Siena, a city celebrated for its medieval charm and rich cultural heritage. A local guide will take you through its narrow streets, unveiling centuries of history. Admire the iconic Piazza del Campo, one of Europe’s most renowned squares, famous for hosting the thrilling Palio horse race. Marvel at the stunning Siena Cathedral, a Gothic masterpiece adorned with intricate details, marble floors, and priceless works of art by masters like Michelangelo and Donatello. Experience the lively atmosphere of this historic city, a proud rival of Florence throughout history.
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3 hours Admission Ticket Free

Piazza Salimbeni

Stroll through Piazza Salimbeni and admire the stunning architecture of the buildings surrounding the square. The iconic Palazzo Salimbeni stands as a symbol of the town’s financial history, offering a glimpse into Siena’s rich past while providing a peaceful and picturesque setting in the heart of the city.
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30 minutes Admission Ticket Free

Duomo di Siena

Follow your guide and admire from the outside the outstanding Duomo di Siena The Duomo di Siena, or Siena Cathedral, is one of the most remarkable examples of Italian Gothic architecture. Dedicated to the Virgin Mary, it was constructed between the 12th and 14th centuries and stands as a symbol of Siena’s rich history and artistic legacy.
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30 minutes Admission Ticket Free

Strada in Chianti

Continue your amazing journew with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.
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2 hours Admission Ticket Free

San Gimignano

Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Medieval Manhattan" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.
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2 hours Admission Ticket Free

Piazza Della Cisterna

Make your way to Piazza della Cisterna, the heart of San Gimignano’s historic center, and savor the internationally acclaimed, award-winning gelato from Gelateria Dondoli.
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30 minutes Admission Ticket Free

Collegiata di Santa Maria Assunta - Duomo di San Gimignano

Admire the Duomo of San Gimignano from the outside, with its impressive Romanesque facade and beautiful positioning in the heart of the town, offering a glimpse of its medieval charm and historical significance.
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30 minutes Admission Ticket Free

Rocca of Montestaffoli

Explore the Rocca di Montestaffoli, both from the outside and within, where you can appreciate its imposing structure and wander through its historic interior. From the top, enjoy breathtaking panoramic views of San Gimignano and the surrounding countryside, immersing yourself in the rich medieval heritage of the town.
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30 minutes Admission Ticket Free

Piazza del Campo

Visit one of the most significant squares in the city of Siena and let yourself be captivated by the imposing "Torre del Mangia". Built between 1338 and 1348, it was designed to match the height of the Siena Cathedral's bell tower, symbolizing the harmony between religious and civic authority in the city.
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1 hour Admission Ticket Free

Show 8 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Please inform us of any food intolerance or allergy in advance

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-6367P149

Traveler Photos

Reviews

4.90
39 reviews

Average 4.90 out of 5 stars based on 39 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars
37
4 stars
1
3 stars
0
2 stars
1
1 star
0
Don't miss out!
On average, this is booked 24 (0) days in advance.
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Things To Do in Florence

Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Key West Private Charters customers.

Filter by:

Q: What is the cancellation policy for the Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CET).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Expert English Only Tour Leader.
  • Free time in San Gimignano.
  • Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi.
  • Sampling of wines, extra-virgin olive oil and regional products.
  • Visit of a typical Chianti Winery with wine tasting.
  • VIP Small Group Tour up to 25 participants.
  • 1 Hour English Only Guided tour of Siena with an Expert Local Guide.
The following is NOT included:
  • Pick up and drop off.
  • Gratuities.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Exclusive Siena and San Gimignano Tour & Chianti Wine Experience is as follows:

  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Exclusive Siena and San Gimignano Tour & Chianti Wine Experience will be included in your confirmation email from Key West Private Charters. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Expert English Only Tour Leader
  • Free time in San Gimignano
  • Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi
  • Sampling of wines, extra-virgin olive oil and regional products
  • Visit of a typical Chianti Winery with wine tasting
  • VIP Small Group Tour up to 25 participants
  • 1 Hour English Only Guided tour of Siena with an Expert Local Guide
  • Pick up and drop off
  • Gratuities

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Please inform us of any food intolerance or allergy in advance
  • Please note that the given order of the visits may change
  • This tour/activity will have a maximum of 25 travelers

Report Product Issue

Activity name