Private Mercedes Tours of San Gimignano and the Wine Country

This fantastic day Gimignano Wine Tour excursion is designed for food and wine lovers staying in Siena and looking for a short taste of the Tuscan countryside. On this private chauffeured tour you will head north from Siena and visit a beautiful winery in the Chianti wine lands such as San Fabiano Calcinaia or Felsina, you’ll enjoy an excellent traditional al fresco lunch in Castellina and a wonderful excursion to medieval San Gimignano, one of the most picturesque villages in Italy.

The Chianti Classico appellation is located between Siena and Florence around the villages of Radda, Castellina and Gaiole. It is the quintessential romantic Tuscan Wine Country you imagine with fairy tale castles crowning hill top villages and lush valleys blanketed in vineyards. After a marvelous VIP winery visit and tasting in a historic cellar and convivial lunch, you’ll head to the darling village of San Gimignano where you’ll enjoy a private guided tour of this lovely town’s most cherished gems such as the medieval towers, the outdoor frescos and much more. On the way back to Siena you’ll stop for a digestivo or coffee in the remarkable walled hamlet of Monteriggioni. Arrive to your hotel in Siena in the early evening. Looking for an excursion from Siena that includes top food, wine, culture and sightseeing and all with the luxury of your own driver? Contact us for more info on this tour.

Tour Highlights:

  • Excursion to San Gimignano & Monteriggioni
  • VIP Wine Tasting in Chianti
  • Private Mercedes Chauffeured Tour
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Sample San Gimignano Wine Tours Itinerary

Medieval San Gimignano

Medieval San Gimignano

10AM Your elegant driver will pick you up from your hotel or villa in or around Siena. Travel out of the city and into the wine country, stopping near Castellina for a visit to a wonderful cellar such as San Fabiano Calcinaia or perhaps Felsina, both stellar estates. You’ll enjoy a walk through the vines and a full tour of the vinification rooms and barrel chambers, followed by a superb tasting of wines. What a way to spend the morning!

Lunch will follow at one of our favorite trattorias in Tuscany, near Castellina. You’ll enjoy classic specialties like Crostini, delicious bruschette drizzled with olive oil and of course fresh pasta and Riserva quality Chianti wine from one of the best cellars. You might finish the meal with homemade Panna Cotta. This is a real treat.

After lunch you will want to stretch your legs and walk off the Vin Santo, and a private guided walking tour of enchanting San Gimignano is in store for you. Enjoy a loop around the village, taking in the lovely Collegiata, the Piazza della Cisterna with its 13th century cistern, and head to the Rocca- the castle fortress- for spectacular views over the ancient towers. You’ll have some free time on your own as well to take in the boutiques, art galleries and charming gourmet shops.

On the way back to Siena you’ll stop at the amazingly preserved hamlet of Monteriggioni, set amid vineyards and enclosed by a medieval wall. This little town is a great place to take photos, go for a walk through picture perfect streets, have a quick coffee or gelato, or perhaps another last vino for the day. You’ll be dropped back at your hotel by about 6PM.

And this concludes your VIP Food and Wine Excursion.

“A VIP Deluxe Wine Tasting Excursion!”

What's Included:

  • Luxury Transportation to and from Siena with English speaking Chauffeur (Mercedes/ Deluxe Minivan) for the full day
  • Private Guide for the day
  • VIP Winery Visit to top name estate
  • Guided walking tour of San Gimignano and Monteriggioni
  • Traditional Lunch at fabulous Trattoria in Wine Country
  • Cellar Tours Wine Gift
  • All Local Taxes

Customer Testimonial:

“The tour was great. As always, Cellar Tours has provided us with a wonderful experience. We especially liked the tour and tasting at Strozzi in San Gimignano. The property was lovely and the people were very warm and inviting. Badia a Passsignano was also a good tour, Maurizio was EXTREMELY knowledgeable about wine. Overall, we enjoyed the tour very much and look forward to our next tour in Piemonte in August ”

Monica Capela, Connecticut.


This is a SAMPLE TOUR ITINERARY. Please note that our private chauffeured luxury tours are totally customized to your needs and price varies according to the number of people in your group (please note tours require minimum 2 guests), specific suppliers included, number of services included,specific dates, transport type etc. Contact us today for more information and we would be delighted to get started on a tailor made detailed itinerary with pricing for you.

  • Our tours are all chauffeured, VIP and with luxury transport- please observe ballpark pricing above.
  • inal price depends on selection of specific suppliers, and if an accompanying guide joins you with the driver or if tour is with driver only.
  • Feel free to contact us with your group size (minimum 2 guests, no maximum group size), travel dates and preferences and we will send you custom pricing.
  • Discounts available for larger groups
  • Please note that our tours are available upon demand for PRIVATE GROUPS and are not scheduled tours for mixed groups.

More Information:

All of our tours are available year round upon request for your private group of minimum 2 people. We organize unforgettable packages in Italy that include wine and adventure touring. If you would like us to customize a private high-end tour of Italy for you

For Your Personalized Quote!

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