Tuscan Day Trip: San Gimignano, Chianti & Montalcino

From€155
11 hours
Siena, Italy

About this activity

Discover the medieval charm of San Gimignano, savor Chianti's renowned wines, and explore Montalcino's historic sites on this immersive Tuscan day trip from Siena.

Highlights

  • Explore medieval San Gimignano's towers
  • Savor Chianti's renowned wines
  • Visit Montalcino's historic sites
  • Enjoy scenic Tuscan countryside views
  • Experience authentic Italian culture

Full description

Immerse yourself in the heart of Tuscany with a guided day trip from Siena to San Gimignano, Chianti, and Montalcino. Wander through San Gimignano's medieval streets, famous for its towering architecture. In Chianti, indulge in a wine tasting at a renowned winery, savoring the region's celebrated reds. Conclude your journey in Montalcino, exploring its historic sites and enjoying panoramic views of the Tuscan countryside. This excursion offers a perfect blend of history, culture, and gastronomy, providing an unforgettable experience of Italy's iconic landscapes.

Included / Excluded

  • Guided tour of San Gimignano, Chianti, and Montalcino
  • Transportation in a comfortable air-conditioned vehicle
  • Wine tasting at a renowned Chianti winery
  • Lunch and personal expenses

Meeting point

Start Location

Unknown location

Important information

Know before you book

  • Tour operates in English; check availability for other languages.
  • Wine tasting is included; inform the guide of any dietary restrictions.
  • Tour may involve walking on uneven terrain; consider your mobility.

Know before you go

  • Wear comfortable walking shoes for cobblestone streets.
  • Bring a camera to capture scenic views and historic sites.
  • Carry a bottle of water to stay hydrated during the tour.

Cancellation policy

Free cancellation up to 1 days before the activity starts

For a full refund, cancel at least 24 hours before the scheduled departure time.

Accessibility

  • Stroller Accessible
  • Easy Public Transport
  • Infant Seats Available

Good to know

  • Customers must be able to climb and descend stairs.
  • Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking
  • Travel in air-conditioned minivan for up to 8 people or minibus for up to 30 people
  • Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.

Traveler reviews

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Wonderful , exceptional...

Wonderful , exceptional experience in Tuscany’s world renowned wine towns. Immersive and comprehensive.

Zenaida_CSep 11, 2026VIATOR

Absolutely surreal

The experience was great. We had the chance to visit multiple towns out in the countryside of Italy near Sienna/Tuscany. Offered exquisite glasses of wine, a lunch, and visited iconic landmarks along the way. Huge shout-out to our tour guide Bianca for making the journey fantastic and an unforgettable experience.

Navigate52558492644Sep 4, 2026TRIPADVISOR

Nicely organized tour,...

Nicely organized tour, great food and wine. San Gimignano is beautiful but packed with tourists (including myself too) during mid day. Would love to visit it during some quieter time if any.

Mei_XMay 31, 2026VIATOR

Great guided experience with Luca

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Christina111196Nov 9, 2025TRIPADVISOR

Buyer beware. Over booked and not what was advertised at all. Big waste of money

Buyer Beware. This tour was a 3rd party vendor My tour 366, who rescheduled the tour and overbooked what was supposed to be an 8-12 semi-private tour to 28 people. The two wineries were not able to accommodate. we ended up in the production area at the last minute, not the tasting room. The bus driver initially pulled into a lovely winery only to back out and take us to another venue twice. The 1st venue clearly was not expecting us and was trying to set up last minute. we could not use the main restroom because there was another tour and we were ushered into some dirty back room bathroom. We were served bread which was moldy. The second tour same thing we pulled into a beautiful estate, only to back out and end up on a small production farm, they were actually working the harvest and it appeared we were fit in last moment. The wine maker came out and poured wine and asked people to come help him. The area we were sent to looked to be where the staff had their breaks. There was supposed to be a tasting for olive oil/balsamic vinegar, that did not happen. our guide when asked said, these things happen it is the busy season, well it is October and not peak season. Not for $668 for 4 people. Such a disappointment. you hear how wonderful Tuscany is, it was our 40th wedding anniversary, and a once-in-a-lifetime trip. I am not by any means a wine snob, but have been to some pretty nice wineries in Napa and Sonoma so I know what to expect. This was not even close. We booked with Viator because of their reputation. Our guide lied to the tour company and said everyone was happy. I have so many photos that I will be sharing on Social media so noone else wastes their money and time. Keep looking if you want that fabulous once in a lifetime Tuscany experience you dreamed of, this is not it

Tamara_LOct 20, 2025VIATOR

Additional information

Customers must be able to climb and descend stairs. Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking