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(291)Florence1 hour
VIATOR4.5(82)TRIPADVISOR4.8(209)

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

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!
Private Siena and San Gimignano tour with dinner
  • Private Group: Siena & Dinner: Private Afternoon in Siena & San Gimignano with Traditional Winery Dinner
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!
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!

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
291 reviews
5
236
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(291)

9
959madisonk
July 16, 2026
Great tour!

Francesca was very knowledgeable and well spoken. She gave us a easily understood description of the places we were seeing and had great recommendations for places to eat

M
madia748
July 16, 2026
Most perfect traditional tuscan experience

Francesca was wonderful and very accommodating because of the extreme heat

E
ermelfamb
July 13, 2026
Wonderful visit to a Chianti vineyard

This tour was absolutely fantastic and a highlight of our trip to Florence! Francesca was a wonderful tour guide, who shared lots of interesting information about Tuscany. Siena and San Gimignano were awesome to see but the highlight of the whole tour was the vineyard and dinner in the Chianti countryside. The food was amazing and it was absolutely beautiful. Best tour we've done in Italy!

P
paulaaT4718JM
July 11, 2026
Fantastic tour

The trip is well organized with a fantastic guide Peter who was amazing. Very knowledgeable, attentive and helpful. The boutique wine was worth it.

F
fadi235
July 11, 2026
Peter a great tour guide

Very organized trip. Peter was very friendly, helpful, and made our trip comfortable and remarkable with great tips about every stop. Very informative person. Had a wonderful experience in the winery that Peter accompanied us to.

C
chrisbX4704PV
July 9, 2026
Great afternoon/evening in Chianti

Christina was great guide and driver. We loved the guided tour of Siena and San G. The vineyard tour and dinner was everything we hoped for and more. Delicious food and wine pairings

M
marksI9668JV
July 6, 2026
Taste of Tucsny

Nice taste if Tuscany. More time in Siena would be good. The winery was enjoyable.

T
T5831VAjessicad
July 6, 2026
Definitely do it!

Such a great experience with great sights and great food.

D
djcee
July 6, 2026
Beautiful Afternoon with Sunset in the country

Wonderful day out in Tuscany and great value for money with a delicious dinner and wine tasting

Y
Y8997DOrossc
July 5, 2026
Best tour of Italy we’ve had

Amazing experience! Recommend highly!!

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