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
• ✓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

• ✕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 you'll do

1. 1

   Towns of Italy indicated meeting point

2. 2

   Arrival in Siena for a guided tour

   ⏱ 2 hours
3. 3

   Free time in San Gimignano, UNESCO Heritage Site

   ⏱ 1 hour
4. 4

   Gourmet Dinner in a Boutique Winery in Chianti

   ⏱ 1 hour
5. 5

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

Availability & pricing

4 tour options available. Pick your exact date & check live availability on the booking page.

Good to know

• 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.