Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape

Highlights

• Private San Gimignano Tour
• Private Transportation
• Optional Wine Tasting

What's included

Itinerary

1. 1

   Florence

   1h 10min

   Scenic Drive from Florence to San Gimignano The tour begins with a relaxing and comfortable ride from Florence in a private air-conditioned VAN. You’ll be accompanied by an English-speaking local guide who will share stories, fun facts, and insights about Tuscany along the way. As you drive through the stunning Tuscan countryside, you’ll follow part of the historic Chianti wine road, passing olive groves, vineyards, cypress trees, and stone villages. Enjoy the landscape, take pictures, and if you'd like, listen to some classic Italian music to set the mood for your day. This journey is more than just a transfer — it’s your first taste of authentic Tuscany. Pick-up can also be arranged from the port of Livorno upon request.

2. 2

   San Gimignano

   1h 15min

   Arriving in the iconic hilltop town of San Gimignano, you'll take a guided walking tour through its historic streets, famous for their medieval towers and unforgettable views. Your guide will lead you through the town’s highlights: • Piazza della Cisterna • Piazza del Duomo • Palazzo Comunale & Torre Grossa (inside and outside) • Collegiata di Santa Maria Assunta After the tour, enjoy some free time to wander the charming streets and try a world-famous gelato at Gelateria Dondoli, multiple-time winner of the Gelato World Cup.

3. 3

   San Gimignano

   2h 30min

   Wine Tasting & Tuscan Lunch at a Local Winery To complete your Tuscan experience, you’ll visit a traditional, family-run winery nestled in the countryside. Here, you'll enjoy a guided wine tasting of several locally produced labels, accompanied by a typical Tuscan lunch with seasonal dishes, local olive oil, and freshly baked bread. It’s the perfect way to relax, taste the essence of the region, and immerse yourself in its food and wine culture — all in a warm, authentic setting.

4. 4

   Siena

   50min

   After lunch and the wine tasting at the winery, you'll continue on to Siena, one of the most enchanting cities in Tuscany. The scenic drive takes about one hour and brings you deep into the heart of the Sienese countryside. Upon arrival, your driver will show you a convenient meeting point and then give you free time to explore the city at your own pace. Stroll through the medieval streets, visit the famous Piazza del Campo, home of the Palio horse race, admire the stunning Siena Cathedral from the outside, or treat yourself to a traditional sweet like ricciarelli or panforte. Siena offers breathtaking views, timeless charm, and the chance to discover its historic districts on your own.

5. 5

   Florence

   1h 10min

   After a memorable day immersed in the beauty, flavors, and history of Tuscany, sit back and relax on the comfortable drive back to Florence. Enjoy the scenic countryside one last time as your guide wraps up the day with a few final insights or lets you unwind in peace.

Before you go

Location