Florence: Siena & San Gimignano with Dinner in a Boutique Winery
Overview
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.
What's 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
- 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
- Guided walking tour of Siena
- 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)
Meeting Location
Via dei Vagellai
22, 50122 Firenze FI, Italy
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Historic Centre of San Gimignano
1 hour Admission Ticket Free
Diadema Wine & Evo
1 hour Admission Ticket Included
Additional Info
- Confirmation is instant and will be received at time of booking
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- 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.
- Please read carefully If your tour is scheduled to take place on or after March 1, 2027, the new meeting point will be: Towns of Italy - Tourist Hub & Cooking School - Florence - Largo Pietro Annigoni, 9A - 50122 Florence
- This tour/activity will have a maximum of 20 travelers
Frequently Asked Questions (7)
Q: What is the cancellation policy for the Florence: Siena & San Gimignano with Dinner in a Boutique Winery?
Cancellation Policy
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Activity code: C-5049CHIANTI007
Traveler Photos
Reviews
Average 4.77 out of 5 stars based on 367 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from Cool Shore Excursions customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CET).
- 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.
- 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.
- Guided walking tour of Siena.
- 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).
There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Florence: Siena & San Gimignano with Dinner in a Boutique Winery is as follows:
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Florence: Siena & San Gimignano with Dinner in a Boutique Winery will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's 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
- 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
- Guided walking tour of Siena
- 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)
Additional Info
- Confirmation is instant and will be received at time of booking
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- 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.
- Please read carefully If your tour is scheduled to take place on or after March 1, 2027, the new meeting point will be: Towns of Italy - Tourist Hub & Cooking School - Florence - Largo Pietro Annigoni, 9A - 50122 Florence
- This tour/activity will have a maximum of 20 travelers
