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Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

icon 8 hours Mobile ticket Free Cancellation
Tickets from € 1,408.00

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Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! If you love to visit the cathedral there will be to pay at the guide directly euro 5 per person or euro 7pp with priority -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano.
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  • Bottled water
  • Private Guide in the city of Siena
  • Onboard Wi-Fi (on request at reservation)
  • Hotel pickup and drop-off in Florence
  • Private Guide in the wine cellar
  • Lunch
  • Gratuities
  • Museum/churches fee
Departure Point

Traveler pickup is offered

Pick up from all hotels or apartments in Florence downtown

  • Siena, Siena, Italy
    Followed by an authorized guide you will visit Siena! Siena is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste local food or buy some gifts!
    120 minutes
  • Chianti Road, Italy
    enchanting country road surronded by greenery of vineyards and olive trees - stop for pictures/shooting
    60 minutes
  • Tenuta Casanova, Castellina In Chianti, Italy
    *As an OPTION* We can organize a Lunch in a Farm where you can taste wines and organic local products. (to be paid on the spot) This option will reduce the time in the cities of Siena and San Gimignano and exclude Monteriggioni.
    120 minutes
  • San Gimignano, San Gimignano, Italy
    A pearl of medieval architecture famous for its tower houses! Free time for the last stop in the incredible San Gimignano, a dive into the Middle Ages.
    60 minutes
  • Chianti Road, Italy
    We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!
  • Specialized infant seats are available
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • A maximum of 7 people per booking
  • Drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs.
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
GeneAndDeanWeen
12 May 2025
I have lived in Italy for nearly 20 years and whenever I have friends or family visiting, I book Massimo as our driver. Some of my most memorable experiences in Italy have been out on an excursion with Chianti Drivers! This April, Massimo picked us up in Florence and took us to San Gimignano and Monteriggioni for time to explore on our own. Next, we headed to an exquisite winery for lunch and a cellar tour, before heading to Siena. Massimo is always exceedingly professional, punctual and polite. I cannot recommend this company enough!
Anne_M
20 Mar 2025
Simone was wonderful. He was prompt, flexible and had a lot of interesting information to share. Our guide in Siena was very knowledgeable.
Richard_H
25 May 2024
Great info provided by Massimo along the way. Viviana gave a tour of Siena. Wine tasting at Emma’s winery was superb!
This tour in Florence is organized by Chianti Drivers private tours

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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