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Guided tour of Siena, San Gimignano and Monteriggioni with Wine Tasting at Chiatni

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11 hrs

Journey into the heart of the culturally rich region of Tuscany in Italy. Get an opportunity to taste four excellent wines in a beautiful winery across the rolling Chianti Hills. Explore magnificent locations in Siena like the Palazzo Pubblico, the Cathedral of Siena, Monteriggioni and the Palio Museum and Oratory.


  • Visit the picturesque hilltop village of San Gimignano on the road to Siena.
  • Walk through the city of Siena with an experienced local guide who will tell you compelling facts about the city and its various attractions.
  • Learn about the defining cultural aspects of the city like the ‘Contrade’ and the Palio Horse-Race
  • Sample up to four different wines and balsamic vinegar in a winery.
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Why You Shouldn’t Miss This

As Italy’s most-frequented province, there is little doubt that Siena is amongst the country’s most beautiful locations. Located in the Tuscany region, Siena is known primarily for its diverse range of historical monuments from the medieval period. Romanesque and Gothic monuments dot the landscape.

San Gimignano, famously known as the Town of Fine Towers, is one of the first attractions on the itenary. With numerous churches like the Collegiate Church and the Church of Sant'agostino, this gorgeous walled town embodies the true essence of medieval Europe.

The Piazza del Campo is one of the most amazing medieval squares in the country. The Palio di Siena horse race is organised in this square twice a year annually. Monteriggioni is another medieval village that is no less beautiful than San Gimignano. The Chianti area, widely acclaimed for its fine wineries and delightful green hills, is the final stop on this tour.

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Your Experience

Your tour will begin at the town of San Gimignano. You can take a few pictures of the charming sights here and the skyline. You will have some free time to look around and have lunch in the afternoon. Your local guide will then take you to the Palazzo Pubblico in the Piazza del Campo square. You can enjoy a relaxing walk through the narrow medieval streets of Siena and marvel at the buildings all around you that seem to be frozen in a different era. The guide will also take you to the Museum and Oratory of Contrada where you will learn more about the history of the city. The museum contains various important historical documents and relics of Palio along with incredible paintings, frescoes and other works of art. You will then proceed to admire the magnificent Cathedral of Siena that was built all the way back in the 12th Century.

The village of Monteriggioni is next on the itinerary. Bask in the rustic atmosphere of the small hamlet. End your tour with an exquisite Tuscan wine tasting session in a cosy winery close to the rolling hills of the Chianti region. You can sample four unique wines, balsamic vinegar and ‘zero food miles’ products, all of which are authentic Tuscan delicacies.

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  • Luxury coach transport
  • Professional local guide in Siena
  • Multilingual tour escort
  • Samples of wines and ‘zero food miles’ products
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  • Lunch
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Know Before You Go


  • Siena, San Gimignano and Greve in Chianti with Wine Tasting in a typical Winery - Normal Cost Option
  • Siena, San Gimignano and Greve in Chianti Semi-independent Tour with Wine Tasting in a typical Winery - Low-cost option


  • The tour begins at 8:30 AM and is available all year round on all days of the week.
  • Please arrive 15 minutes before the scheduled departure.
  • The tour lasts for 11 hours.

Guide Languages

  • English, Spanish, Italian, Dutch and French
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Strict Cancellation Policy

This experience cannot be cancelled, amended or rescheduled.

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Ratings & Reviews
Out of 5
Very Good
Betty Lambert
Reviewed in September, 2018

What a day it was, tasting four excellent wines in a beautiful winery across various cities. Highy recommend it to all

Homer Wells
Reviewed in September, 2018

A unique and authentic experience of the various cities and its traditions. Must do this

Bobby Wilkerson
Reviewed in August, 2018

Headout has become an indisputable part of our travel experiences now. Just love them

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My Tickets

You will receive an email confirmation along with your mobile voucher shortly. You can show your mobile or printed voucher along with some valid photo ID before the tour commences.

Meeting Point

Piazzale Montelungo - Caf Tour and Travel - Gray Line Yellow Street Sign.


This tour is valid for the date selected at the time of booking.

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Piazzale Montelungo, Yellow Street Sign, Florence

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