Tours/Florence/Florence: Siena & San Gimignano with Dinner in a Boutique Winery
Viator · group up to 20 pax

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

4.7(311)Florence1 hour
VIATOR4.5(82)TRIPADVISOR4.8(229)

Description

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.

Tour Options

Private Siena and San Gimignano tour with dinner
  • Private Group: Siena & Dinner: Private Afternoon in Siena & San Gimignano with Traditional Winery Dinner
Essential Coach Tour & Dinner
  • Afternoon with Dinner : Siena & San Gimignano by coach - top Tuscan sights and a typical dinner at a winery—great experience, budget-friendly price!
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!
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!

Itinerary

Pass by

Towns of Italy indicated meeting point

120 min

Arrival in Siena for a guided tour

60 min

Free time in San Gimignano, UNESCO Heritage Site

Admission included60 min

Gourmet Dinner in a Boutique Winery in Chianti

Pass by

Return to Florence and end of the tour at the initial meeting point

Highlights

Free WiFi on board
English speaking driver/tour leader
Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option
Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan
Guided walking tour of Siena
Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included)
Visit of a winery with wine tasting
Surprise tasting in Siena
San Gimignano visit with free time
Free Time in San Gimignano

What's included

Included
Free WiFi on board
English speaking driver/tour leader
Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option
Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan
Guided walking tour of Siena
Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included)
Visit of a winery with wine tasting
Surprise tasting in Siena
San Gimignano visit with free time
Free Time in San Gimignano
Not included
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)

Traveller Ratings

4.7
311 reviews
5
256
4
31
3
12
2
8
1
4

Important Information

  • 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.

Reviews(311)

P
P9806MLjulier
August 21, 2026
Fun evening in Siena, San Gimignano, and at a boutique winery.

Wonderful day trip away from the hustle and bustle of Florence. Our driver, Christina, was friendly, efficient, and knowledgeable. We had a wonderful time!

8
844marl_new
August 13, 2026
Great and interesting tour

The driver Francesco was a super tour guide who made the trip very lively and interesting. We would recommend this tour to anyone. Siena is beautiful and is a must-visit. San Gimignano is also definitely worth a visit.

L
lauraaX2789KZ
August 13, 2026
Tuscany Wine Tour

Francesco was amazing! He was entertaining, kind, and an all around blast to have as a driver! He enlightened us with history and showed us beautiful sights along our way to Siena and a wine tour in Chantai! Highly recommend!

V
V3642AWnatashad
August 11, 2026
A wonderful introduction to Tuscany

This was an excellent change from the usual tours in Florence, and a great introduction to the other must-see towns of Tuscany. The group was sized perfectly and felt intimate. Our guide at Siena was excellent and managed to cram in a lot of sights in a short time. We had plenty of time to get a taste of San Gimigiano, and the dinner at the winery felt homely - like having a meal at a friend’s home. Most of all, our driver/guide was very accommodating and helpful to my family, who genuinely appreciated her hospitality. I highly recommend this tour if you’re looking for a wider taste of Tuscany!

J
jameskD8990LE
August 10, 2026
Fun times on Tuscany Tour with Family

Tour guides on the school leg were very nice and helpful. Cities were both fascinating places - distinctly ancient but very different. Winery was excellent and authentic experience, and the owner and staff were very knowledgeable and hospitable. Some minor feedback: In Siena, it would be great to allow for time to visit the Duomo. But overall an excellent experience.

M
mldm23
August 9, 2026
Siena and San Gimignano Tour with Federico

Our tour with Federico was wonderful and authentic. We will have memories forever of the excellent service and thorough explanations of amazing locations including San Gimignano, Siena, Fattoria Di Bagnolo. Federico was incredible and so informative. I highly recommend!

P
P1377BJkatel
August 9, 2026
Such a special memory for our family!

This was such a special family experience! Our tour guide, Federico, was incredibly friendly and knowledgeable, making our tour very personal and memorable. San Gimignano was lovely, and Siena was fabulous with a great guide. The winery was exceptional for wine as well as food and the hospitality of our hosts. Incredible all around! Can’t recommend it enough.

S
sylviaaR7981FC
August 9, 2026
Medieval & Delicious

Outstanding experience. San Gimignano was unforgettable. Our guides were knowledgeable and FUN! Ate the best gelato in all of Italia. The medieval aura was palpable and unparalleled. And to finish off, a delicious meal paired with stellar regional wines presented and elaborated by very friendly and personable locals. Thank you!!! S&N

9
96pranavt
August 9, 2026
Amazing experience

The whole tour was great. Romana was great. She was very informative and friendly. She took special requests and made my family's experience amazing.

D
DEL772
August 6, 2026
Daria was awesome

Daria was a fantastic guide and driver. She shared so many tidbits that really accentuated the tour. This was my daughter's favourite part of her visit to Italia. Grazie!

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