Experience

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

4.71(339)Chianti· Vineyards · slow roadsEnglish4 options

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.

Languages
English

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
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

Meeting point & pickup

Meet at the designated start point

Cancellation

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

Choose a tour option · 4

4 versions of this tour. Pick a date to see prices, start times and what's still open.

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!
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!
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!

Where you'll be

from€107.00/person
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Around Chianti

Places worth planning around while you're in the area.