From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape

Overview

Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San Gimignano, led by a local expert. Discover medieval towers, artisan shops, and breathtaking views in this UNESCO-listed town. Enhance your day with an optional wine tasting and Tuscan lunch at a renowned Super Tuscan winery, where you’ll sample Vernaccia di San Gimignano and other local labels in an authentic countryside setting. After lunch, continue to Siena, one of Tuscany’s most enchanting cities. Enjoy free time to explore Piazza del Campo, admire the Siena Cathedral from outside, and stroll the historic streets at your own pace. This flexible experience can be tailored to your cruise schedule, with guaranteed on-time return. Perfect for travelers seeking a mix of history, beauty, and flavor in a single day.

What's included

• ✓Private transportation
• ✓Guida privata

• ✕Wine tasting and Lunch
• ✕Museum Tickets

What you'll do

1. 1

   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.

   ⏱ 1h 10m
2. 2

   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.

   ⏱ 1h 15m
3. 3

   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.

   ⏱ 2h 30m
4. 4

   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.

Availability & pricing

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
• Service animals allowed
• Public transportation options are available nearby
• Specialized infant seats are available
• Travelers should have at least a moderate level of physical fitness

Cancellation policy

All sales are final. No refund is available for cancellations.