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

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

By Untracked Italy

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Features

8h
Mobile voucher
Instant confirmation
Selective hotel pickup
Multiple languages

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 travellers seeking a mix of history, beauty, and flavour in a single day.

Activity location

Florence
- Florence, Italy

Meeting/Redemption Point

Florence
- Florence, Tuscany, Italy

Check availability

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

8h
Opening hours: Thu 10:00-18:00
English

Pickup included

Travellers

Languages available

Price details

£389.68 x 1 Adult£389.68

Total

What's included, what's not

Private transport
Guida privata
Wine tasting and Lunch
Museum Tickets

Know before you book

Infants and small children can ride in a pram or stroller
Service animals allowed
Public transport options are available nearby
Specialised infant seats are available
Travellers should have at least a moderate level of physical fitness
In accordance with UK consumer law, activities services are not subject to the right of withdrawal. Supplier cancellation policy will apply.
This activity is provided by a professional trader (a party acting within their trade, business or profession).

Activity itinerary

Florence

1h 10m

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.

San Gimignano

1h 15m

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.

San Gimignano

2h 30m

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.

Siena

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.

Florence

1h 10m

After a memorable day immersed in the beauty, flavours, 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.

Location

Activity location

Florence
- Florence, Italy

Meeting/Redemption Point

Florence
- Florence, Tuscany, Italy

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