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San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence

5 (3)

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence

5 (3)
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Experience the best of Tuscany on a private, exclusive, and customizable tour of San Gimignano and Chianti Classico. Step into a luxury Mercedes sedan/minivan with an English speaking driver and embark on an 8-hour adventure through the breathtaking Tuscan countryside. Indulge in traditional Tuscan cuisine, toasting with a glass of Sangiovese or Chianti Classico, and discover the secrets behind the world-renowned wine making process. Sample distinctive wines, exquisite olive oil, Vin Santo, and Grappa as expert guides unravel the history and flavors of this enchanting region. Travel back in time as you stroll along the walls of Monteriggioni and immerse yourself in the medieval charm of San Gimignano, surrounded by its iconic towers. With free Wi-Fi on board, refreshing refreshments, and all gas, tolls, and VAT taken care of, this private tour promises an unforgettable experience.

About this experience

  • Admission Not Included
  • 8 hours
  • Suitable for 2-8 Participants
  • Private Tour
  • Non Refundable There is no return, refund or cancellation possible with this product
  • Hotel pickup and drop-off
  • Free Wi-Fi on board
  • Private tour
  • Gas - Tolls - VAT
  • Refreshments on board
  • Gratuities
  • Alcoholic beverages
  • Lunch

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

Chianti Road

Enjoy typical Tuscan cuisine in a countryside setting, toasting with a glass of Sangiovese or Chianti Classico. Take in the heart-stopping beauty of the Tuscan countryside that leads into the Chianti Classico wine country. Sample distinctive wines, exquisite extra-virgin olive oil, Vin Santo and Grappa, while expert guides reveal the secrets behind this world renowned wine making process. Wine tasting costs not included.

Admission Not Included

San Gimignano

Travel back a thousand years and discover Monteriggioni, where you will take a walk along its walls and gaze out onto its surrounding, stunningly timeless countryside. Make a pilgrimage to postcard perfect San Gimignano, where 13 of its original 72 towers will envelope you and provide a striking and enchanting backdrop to your visit.

More about this experience


Experience the beauty and flavors of Tuscany like never before on the San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence. This exclusive, customizable tour offers a unique opportunity to discover the hidden gems of the region in a luxurious Mercedes sedan or minivan with an expert English speaking driver. From the moment you step into the vehicle, you'll be treated to a comfortable and informative journey through the picturesque landscapes of San Gimignano and Chianti Classico.

What to expect?

Indulge in the rich history and breathtaking scenery of San Gimignano, where you'll be transported back in time as you explore its ancient walls and marvel at the iconic towers that have stood the test of time. Immerse yourself in the charm of this postcard-perfect town and let its enchanting atmosphere captivate your senses. As you venture further into the heart of Tuscany, you'll be treated to the exquisite flavors of Chianti Classico, renowned for its world-class wines and delectable cuisine. Savor the opportunity to taste and learn about the region's finest wines and indulge in a culinary journey that will leave you craving for more.

Who is this for?

This private tour is perfect for anyone seeking an intimate and personalized experience of Tuscany. Whether you're a wine enthusiast, a food lover, or simply someone who appreciates the beauty of the Italian countryside, this tour is designed to cater to your specific interests and preferences. Couples looking for a romantic getaway, families in search of a memorable vacation, or groups of friends seeking a unique adventure will all find something to cherish on this tour.

Why book this?

When it comes to exploring Tuscany, this private tour stands out from the rest. With the freedom to customize your itinerary and the flexibility to spend as much time as you desire at each location, you'll have the opportunity to immerse yourself fully in the beauty and flavors of the region. The luxury Mercedes sedan or minivan ensures a comfortable and stylish journey, while the knowledgeable English speaking driver will provide valuable insights and recommendations throughout the tour. With hotel pickup and drop-off, free Wi-Fi on board, and refreshments included, every aspect of your experience is designed to exceed your expectations.

Good to know

During the tour, you'll have the chance to visit the charming town of Monteriggioni, where you can take a leisurely walk along its ancient walls and soak in the stunning views of the surrounding countryside. Lunch, gratuities, and alcoholic beverages are not included in the tour, allowing you the freedom to choose your own dining experience. With gas, tolls, and VAT covered, you can relax and enjoy the journey without any additional costs or worries. Prepare to be swept away by the beauty, history, and flavors of Tuscany on this unforgettable private tour.


Travelers who have experienced the San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence have been enchanted by its charm and authenticity. They rave about the knowledgeable and friendly drivers who go above and beyond to make the experience truly memorable. The flexibility to customize the itinerary and the opportunity to taste and learn about the region's renowned wines have left a lasting impression on visitors. Overall, the tour has received glowing reviews, with travelers praising the stunning landscapes, the delicious food and wine, and the exceptional service. Don't miss out on the chance to embark on this extraordinary journey through Tuscany's hidden gems.



5 (3)


Maurizio was a fantastic guide and driver. He had a wealth of knowledge for Tuscany and the stops on the tour. The lunch at the boutique winery, Azienda Agricola Rocca, in Chianti was like a dream or a movie. Eating lunch amongst the olive trees and eating the homemade food was a highlight of our trip. The second winery, I Fabbri di Susanna Grassi had some of the best Tucson wines we have ever had. We even ordered some for our son’s wedding this summer! We would highly recommend We Drive You Tuscany!


Can’t say enough great things about We Drive You tour we went on. Roberdo was amazing. Picked us up on time in a very clean van. He was very friendly and provided so much information about Tuscany. Would definitely use this company again!!


We were with 11 people and Tomas arranged a great tour. He took a nice road to the vineyards with breathtaking views. He knows a lot about the region and he makes sure you’re comfortable. The wineries were very different from eachother, and both very nice to visit. Good price/quality ratio
Collected by Evendo, Tripadvisor & Viator
2024-03-01 13:48
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