From Florence: PRIVATE Siena and San Gimignano with wine tasting

Embark on a private exploration of Siena, San Gimignano, and Monteriggioni, and immerse yourself in the medieval charm of Tuscany. Secure bookings, guaranteed departures, and small group sizes make us the top choice for an authentic Tuscan experience.

Duration: 9 hours, 30 minutes
Cancellation: 1 day learn more
Highlights
  • Florence - The tour begins in a premium minivan equipped with an English-speaking driver, air conditioning, and complimentary water.
  • Siena - The first stop is Siena, where a local guide will take you on a one-hour tour of iconic spots like Piazza del Campo and Piazza del Duomo, allowing you to soak in the town’s unique medieval charm.

Afterwards, you’ll have an hour of free time to explore the Duomo, shop, or savor local delicacies.

  • Castello Monteriggioni - Returning to the minivan, we’ll head to the charming town of Monteriggioni. Built in 1213, its renown was so great that even the famous poet Dante Alighieri mentioned its circular walls in the Divine Comedy.

Here, you’ll have the opportunity to enjoy a fantastic lunch and sample local wine in a picturesque setting.

  • San Gimignano 1300 - On the way to San Gimignano, you’ll be treated to the stunning Chianti landscape, filled with vineyards and olive groves.

Upon arrival, you’ll have free time to explore “The City of Beautiful Towers,” a UNESCO World Heritage site known for its medieval architecture.

  • San Gimignano - Enjoy a wine tasting at a local winery, where you’ll learn about vineyard techniques, the winemaking process, aging, and, of course, how to appreciate different wines! Plus, sample some local olive oil.
  • Florence - The tour concludes with a comfortable return to Florence, just in time to catch the sunset!
What's Included
  • Private tour
  • Luxury car or premium van at disposal
  • Professional guide in Siena
  • Guided Wine tasting
  • Lunch
  • In-vehicle air conditioning
  • Free time in all the cities
What's Not Included
  • Hotel pickup and drop-off
  • Gratuities
Additional Information

Discover 3 of the most authentic towns nestled in the heart of the Tuscany countryside.

Siena, the famous Palio city, San Gimignano, UNESCO heritage and Monteriggioni, one of the most enchanting Italian walled town.

Taste local wine, including the DOC Tuscanian white wine!

“Explore the essence of Tuscany: Siena, San Gimignano and Monteriggioni are waiting to be discovered!!!”

WHY CHOOSE US?

Secure bookings, Guaranteed Departures!

  • A maximum of 8 people per booking
  • A minimum of 2 people per booking is required
  • No minimum age required
  • Children must be accompanied by an adult
Location
Cantinetta Antinori
Piazza degli Antinori
Please, get the meeting point at 8:00am
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(6 Ratings)
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1 star
184mattiar
Jan 22, 2024
Perfect day in Tuscany! - Perfect day! Our driver was always on time and very gently and relaxing. The guide was super informative and kept our attention at the best! Time into the city was just perfect and or wine tasting was just amazing! Perfect day!
Review provided by Tripadvisor
Sue_g
Aug 7, 2023
Great tour a family with 3 boys - Karim our guide and driver was amazing. This tour was tailored to us and our family, with 3 boys obsessed with the Assasins Creed game. We spent a lot of time in Monteriggioni and my kids loved it. Siena was very interested and beautiful as was San Gianmgno. Great tour and the way to go with kids.
Review provided by Viator
Roseworldtravelers
Sep 23, 2019
Private Tour of Siena, San Gimignano and Monteriggioni - This was our second private tour with CiaoFlorence. We were so excited to have Elvis as our personal guide again!! Elvis was very flexible, professional and entertaining. The tour was scheduled for eight hours but we were getting back to early so Elvis planned a few surprise stops to make sure we got the most of our trip. We couldn’t have had a better day or guide!! Will book again with CiaoFlorence and request Elvis in a heartbeat. You know your guide is great, when you end up taking selfies together!
Review provided by Tripadvisor
Ursula_z
Jun 27, 2019
Lovely way to discover the real tuscany - I really want to recommend this tour because for us has been perfect.. The driver Luca was helpful and friendly with us explaining everything while he was driving. We have had a local guide in Siena called Maria whom was very knowledgeble and careful with our needs. At lunch time we went to a local restaurant in Monteriggioni where the chef showned us different kinds of flours and also the way to make "pici", typical pasta from tuscany. At San Gimignano don't miss the gelato which is the best I've ever had!!!
Review provided by Viator
Explorer67344890479
Jun 27, 2019
A perfect day trip... - I was in this tour with my partner and on the minivan we were travelling there was just another family of 4 people. The guide Anna in Siena was very knowledgeble and ,with her, has been easy walking through the city center. The lunch in the typical "trattoria" was really good and the homemade pasta simply amazing!!! In San Gimignano we have had 2 hours of free time where we have been advised to try the awarded "best ice cream in the world"...delicious!! UZ
Review provided by Viator
Richard_l
Jul 30, 2018
Loved it! - It was just 4 of us, which was comfortable in the van. The driver was not a tour guide, we had tour guides at the stops. The wine and lunch was good.
Review provided by Viator
Gaye
Nov 3, 2017
We were the only two to take this... - <p>We were the only two to take this trip in the late season and it was very gratifying that the company was willing to do it for just us two. The tour guide in Siena was a delightful young woman whose grasp of the events and sites was communicated expertly. Our visit to the Palagetto vineyard/winery/olive oil press was educational and delicious. The food pairing provided with the wine tasting was a very ample and excellent lunch. The young woman who was our guide there Julia was absolutely engaging and knowledgeable. We thought this was a tremendous bargain for the price and recommend it most enthusiastically.</p>
Review provided by Viator
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1 Adult
October 2024
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