Daily excursion of Chianti and Castles, departing from San Gimignano or Siena

Day Trip in Chianti Region, departing from Siena and San Gimignano

7 h
Day Trips & Excursions
difficulty Easy
Wheelchair Not Accessible
Best reviews
( 4.9 )2 reviews

I would highly recommend this to anyone of all ages, families and couples.

Jessica W
Pick up includedImmediate confirmation

Tuscany Day Trip of Chianti and Monteriggioni, from Siena and San Gimignano

Discover the unique countryside of the Chianti region of Italy with our amazing Chianti and Castles tour from Siena and San Gimignano. You will have the chance to admire the best attractions of this beautiful area and to taste the famous Chianti wine and olive oil with our experience!

Daily excursion of Chianti and Castles, departing from San Gimignano or Siena highlights: 

  • Discover the countryside of the Chianti regions with a unique tour
  • Taste the unique flavor of the Chianti wine with two tasting sessions and taste some delicious olive oil
  • Admire the charming landscapes of Tuscany and immerse yourself in the picturesque scenery you have always imagined
  • Pass along some of the best attractions of Chianti, churches, castles and villages and visit Monteriggioni
  • Half a day experience from Siena or San Gimignano, perfect for food and culture lovers

Let yourself immerse into the intimate and romantic atmosphere of the Chianti region in Tuscany. Our amazing and unique tour departing from San Gimignano or Siena offers you the opportunity to discover one of the most authentic and fascinating parts of Italy and maybe the world. Chianti is the place where one of the most famous wines in the world is made and also a very attractive place, with a wide range of attractions and beautiful landscapes.

Explore the Chianti region and taste its famous wine

Explore the Chianti region and learn more about its wines and its charm. Our exclusive Chianti and Castles Tour include transfer and transportation with a comfortable minivan with maximum 8 places, a bilingual guide, visits and wine tasting sessions. You will have the chance to see the most touching places of Chianti, including ancient churches, medieval castles and small traditional villages, with a timeless charm and a unique atmosphere.

Visit the traditional wineries of the Chianti

Beyond all these, Chianti is the land of wine and there are various types that come out of Chianti and reach the farthest places in the world. The unique Chianti and Castles Tour includes visits to two famous wineries of the region, with wine tasting sessions that will teach you the different properties of the Chianti wine. The wine will be served with other typical Tuscan specialties, for a full Tuscan experience. Passing through some exceptional landscapes and past the fascinating attractions of Chianti, our unique tour is the perfect activity out of the city.

Explore the incredible fortress of Monteriggioni

This incredible one day tour will allow you to discover with a self-guided tour the famous and incredible fortress of Monteriggioni, as well as other typical villages in Chianti. There, you will have some free time to spend among the beautiful shops and cafès.
Finally, you will enjoy a second tasting of olive oil in another typical winery!

More Things To Do in Tuscany

If you are staying in San Gimignano, and you want to explore the wonderful landscape of Chianti, you might be interested in the Chianti Tour with Brunello Wine tasting or in the Tuscany Day Trip to San Gimignano and Chianti!
Also, if you want to discover two charming villages that overlook the Ligurian sea, we recommend the Tour of Portofino and San Fruttuoso from Tuscany!

  • Pick-up 
  • Chianti 
  • Drop-off
  • Pick-up and drop off service on request
  • Travel by minivan with air conditioning for a maximum of 8 people
  • Expert multilingual escorts (English-Italian)
  • Wine, oil and balsamic vinegar tasting
  • Snack with sliced cured meats and typical salami
  • Small group tour
  • Self guided tour of the Monteriggioni fortess 
  • Tour of two wine cellars 
  • Tips (optional)


Meeting point: 

The tour departs from 16th November 2017 to 14th March 2018:

  • San Gimignano, 12:00 PM
  • Siena, 1:00 PM

From 15th March 2018, the tour departs:

  • San Gimignano, 1:00 PM
  • Siena, 2:00 PM

During the booking process remember to choose the appropriate meeting time for your starting point. Please, let us know the name and the hotel address for the pick up.
Meeting point information and local telephone numbers at your destination are included on your Confirmation Voucher.


We reccomend wearing comfortable clothing and shoes.
The duration of this tour depends on the location from which it departs. It will have a duration of 7 hours departing from San Gimignano and a duration of 5 hours departing from Siena.
Pick-up and drop off services are available for this tour on request.
This is a small group tour. The maximum capability of the mini van will be 8 passengers. English and Italian tours are available with a minimum of 2 participants.
This tour is not suitable for people with impaired mobility. Customers must be able to climb and descend stairs.
Infants from 0 to 2 years of age will be free of charge. Children between 3 and 12 years old will pay a reduced price.

Confirmation will be received at time of booking. You will receive a voucher. This is your ticket and proof of purchase.

Reviews of Day Trip in Chianti Region, departing fr...

Reviewed by Jessica W from Australia


My mother and I did 'the best places in Tuscany' tour. I would highly recommend this to anyone of all ages, families and couples. The tour was very enjoyable and if you want to see another part of Italy, it's fantastic. Our tour guide Chiara was very informative with the history on each place we visited. We also had time to visit the places and walk at our own pace and see the famous cities and small villages. The only bit of feedback I would suggest is longer time at Pisa, so you can go inside the Cathedral and Leaning tower if you wish. Lunch in the wine bar with wine tasting was a lot of fun and you had a chance to interact with the other members on the tour. Overall I thoroughly enjoyed the day and we meet some lovely travellers.
Reviewed by WildTT from Italia

Chianti Tour

Un'esperienza unica. Immersi nelle bellezze del chianti, tra vitigni e fortezze medievali abbiamo trascorso una giornata indimenticabile. L'accompagnatore e la guida hanno contribuito con la loro cortesia a rendere ancora più piacevole l'esperienza. Non vedo l'ora di poter ritornare e provare altri tour.