Overview

Escape the city and immerse yourself in the heart of Tuscany. Enjoy a private, full-day journey through medieval hilltop towns and rolling vineyards with a personal driver and luxury hotel pickup.

Experience the quintessential Tuscan lifestyle on this private day trip from Florence. Designed for those who value comfort and exclusivity, this tour takes you beyond the tourist crowds of Florence to the UNESCO World Heritage sites of Siena and San Gimignano. Complete with a traditional Tuscan lunch and wine tasting, this is the ultimate sensory journey through Italy’s most beautiful countryside.

Highlights

• Door-to-Door Luxury: Enjoy the convenience of private hotel pickup and drop-off in Florence in a premium, climate-controlled Mercedes vehicle.

• Siena’s Medieval Majesty: Explore the home of the famous Palio horse race, the stunning Piazza del Campo, and the magnificent Siena Cathedral.

• The "Manhattan of the Middle Ages": Wander through the iconic towers of San Gimignano and taste world-champion gelato.

• Exclusive Chianti Lunch: Stop at a hand-picked, family-run estate for a traditional multi-course lunch paired with world-class Chianti Classico wines.

• Panoramic Views: Drive through the scenic "Chiantigiana" road for breathtaking photo opportunities of olive groves and vineyards.

Detailed Itinerary

1. Florence Hotel Pickup: Your professional English-speaking driver meets you at your hotel lobby at 8:30 AM to begin your relaxing journey southward.

2. Siena Exploration: Step back in time in Siena. Walk through its narrow brick streets and learn about the historic "Contrade" (districts) that define the city's unique culture.

3. Vineyard Lunch & Wine Tasting: Head into the heart of the Chianti hills. Relax at a private estate where you will enjoy farm-to-table Tuscan specialties, including local cheeses, cured meats, and homemade pasta, perfectly paired with the estate's own wines.

4. San Gimignano Highlights: In the afternoon, visit the skyline of San Gimignano. Enjoy free time to climb the Great Tower or shop for local saffron and handmade leather.

5. Return to Florence: Enjoy a scenic drive back to your hotel, arriving in time for your evening dinner plans.

Why Book a Private Tour from Florence?

Unlike crowded bus tours, our private Siena and San Gimignano trip allows you to move at your own pace. Want to spend an extra 30 minutes for a second gelato in the square? No problem. Our drivers are local experts dedicated to providing a personalized, stress-free experience that prioritizes your comfort and interests.

"A perfect day! The lunch at the winery was the highlight of our entire trip to Italy. Highly recommended for couples and families." – 2025 Traveler Review

Tour Essentials & Inclusions

• Duration: Approximately 8–9 hours.

• Pickup/Drop-off: Your Hotel or Airbnb in Florence City Center.

• Vehicle: Luxury Mercedes Sedan or Van (WiFi and Water included).

• Lunch: Full Tuscan lunch and wine tasting (included or optional based on selection).

• Language: Professional English-speaking Driver-Guide.