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

New To The Site! Florence, Italy

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7 to 8 hours (approx.)
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Instant confirmation

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
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Meeting and Pickup

Pickup point
Pickup details

We will coordinate the meeting point directly with the traveler. Pick-up is available from the hotel, Livorno port, or the airports of Pisa or Florence. Please note that the final rate may vary slightly depending on the chosen pick-up location.

OR
Meeting point

Florence
Metropolitan City of Florence, Italy

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

What To Expect

Florence

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.
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1 hour 10 minutes • Admission Ticket Free

San Gimignano

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 AssuntaAfter 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.
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1 hour 15 minutes • Admission Ticket Free

San Gimignano

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.
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2 hours 30 minutes • Admission Ticket Free

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.
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50 minutes • Admission Ticket Free

Florence

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.
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1 hour 10 minutes • Admission Ticket Free

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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available

Frequently Asked Questions

(6)

Q: What is the cancellation policy for the From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape?

A: This tour is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded. Read more Apr 2025

Cancellation Policy

This tour is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded.

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Activity code: C-381819P14


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What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Private transportation
  • Guida privata
  • Wine tasting and Lunch
  • Museum Tickets

Additional Info

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available

Report Product Issue

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Non-refundable

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

This tour is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded.

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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