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Florence: Siena & San Gimignano with Dinner in a Boutique Winery

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Overview

Available languages

English

Mobile ticket

Discover the best of Tuscany in one magical afternoon!

Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location.

Looking for the full Tuscan experience?

Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.

Additional Info

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Specialized infant seats are available

Suitable for all physical fitness levels

The tour operates regardless of weather conditions

Semiprivate Tuscany Grand Tour Option: Choose the Grand Tour upgrade for a full-day experience starting at 8:00 AM. Discover the highlights of Tuscany in one unforgettable journey: visit Siena with a guided walking tour and a surprise tasting, enjoy free time in the medieval town of San Gimignano, savor a traditional Tuscan lunch, then continue to Pisa to admire the stunning Piazza dei Miracoli and the iconic Leaning Tower (tower tickets not included). The experience includes round-trip transportation from Florence in a luxury Mercedes minivan with free Wi-Fi, an English-speaking driver/tour leader, and all the charm, history, and flavor of Tuscany in one complete itinerary.

Cancellation Policy

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

What‘s Included

Free WiFi on board

Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option

Surprise tasting in Siena

Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan

San Gimignano visit with free time

Guided walking tour of Siena

Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included)

English speaking driver/tour leader

Visit of a winery with wine tasting

Free Time in San Gimignano

Gratuities

Hotel pickup and drop-off

We are sorry to inform you that pets are not permitted on our tours

Tuscany Grand Tour Option: Entrance ticket to the Tower of Pisa (purchase on-site if time allows)

What To Expect

1

Florence

Towns of Italy indicated meeting point

Admission Not Applicable
2

Siena

Arrival in Siena for a guided tour

2 hours • Admission Not Applicable

Options

Essential Coach: Siena &Dinner

Afternoon with Dinner : Siena & San Gimignano by coach - top Tuscan sights and a typical dinner at a winery—great experience, budget-friendly price!

Semiprivate Tuscany Grand Tour

Upgrade to the Grand Tour:: Full-day (12h) with 8 AM departure: Siena, San Gimignano, Chianti, Pisa & Tuscan lunch—semiprivate journey (max 8) in style!

Small Group: Siena & Dinner

Afternoon with dinner: Siena & San Gimignano in a premium small group (max 20) by Mercedes minivan—top-tier tour with winery dinner included!

Reviews

4.53

193 reviews

Total reviews and rating from Viator & Tripadvisor

143
26
12
8
4

  • Terrific tour

    Maryann S,

    Nov 12, 2025

    - Review from Tripadvisor

    5.00

    Grace was informative and very personable. She spoke of the history of the region as we dove through each region. She elicited questions in a friendly manner wanting to know more about our group to enrich her presentation

  • Amazing!!!

    757kemberlys,

    Nov 7, 2025

    - Review from Tripadvisor

    5.00

    Excellent tour! Winery was awesome! Winery owner is the sweetest! This was such a great experience! I learned so much about the making of the wine and what to pair each wine with. AND… the dinner was AMAZING!

    757kemberlys's photo 1

  • Tour with Dinner

    494karthika,

    Nov 7, 2025

    - Review from Tripadvisor

    5.00

    Excellent guided tour matched with eccellente dinner and Wine testing at winery. This was in Seina and San Giammamo. Personable and detail oriented

  • Afternoon experience

    Roam58802392996,

    Oct 29, 2025

    - Review from Tripadvisor

    5.00

    Was great! Thanks claudia! Afternoon tour end of october was a bit late but it was still great!! Especially the wine farm at the end!!

  • You deserve this!

    X6758KSjimmyb,

    Oct 25, 2025

    - Review from Tripadvisor

    5.00

    Such a great tour and experience, winery part and family vineyard was fabulous! The small towns were a nice place to visit away from Florence. Smaller and less people.

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  • Beautiful tour!

    718randir,

    Oct 22, 2025

    - Review from Tripadvisor

    5.00

    Lorenzo was an amazing tour guide! So patient, on time, and knowledgeable. Answered all our questions we had on the way! All of the stops on the tour were beautiful and amazing! I would love to some back and do it again some day.

  • Great experience!

    cindyhall04,

    Oct 19, 2025

    - Review from Tripadvisor

    5.00

    Guides were incredible and the locations chosen were breathtaking. Small note for feedback was the van was quite small and felt squishy but overall really glad we went and would do it again!

  • Charming little towns and winery tour

    Bryan T,

    Oct 18, 2025

    - Review from Tripadvisor

    4.00

    Guides were friendly and knowledgeable. Sienna and San Gimignamo are just like the old Italian towns you see on TV. Little stone streets with shops and restaurants all around with all the activity surrounding the squares. Dinner at the winery was really nice with food and reasonably priced wines if you choose to purchase. The son of the owner was there to tell us about each wine. No high pressure sales either. Only issue was the bus we were on was really cramped with little to no leg room, and I am average height. Also, A/C on bus was a little lacking.

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  • Great

    Alejandra P,

    Oct 18, 2025

    - Review from Tripadvisor

    5.00

    Peter was an amazing guide tour! Provided lots of information and historical facts about the sites we visit. The only thing to improve will be to have free time in Siena for a coffee or shopping.

  • City escape

    Michael W,

    Oct 17, 2025

    - Review from Viator

    5.00

    It was a nice ride through the part of Florence that you don’t see when downtown. Very beautiful. Guide was good energy and sense of humor.

From €179.00

4.53
193 reviews
Check availability

Want a private experience? Upgrade to a private tour

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