Tuscany Day Tour: Explore Medieval Siena, San Gimignano, Monteriggioni with Chianti Wine Tasting

Embark on a full day tour of Tuscany, exploring the medieval towns of Siena, San Gimignano, and Monteriggioni. Indulge in a Chianti wine tasting and soak in the breathtaking views. A perfect day-out to relax and replenish your spirits.

Duration: 10 hours, 30 minutes
Cancellation: 24 hours
Highlights

The tour starts from Florence and leads you to the atmospheric Medieval gem of Monteriggioni. It was built in 1203 and became a strategic garrison town with its 14 towers, Dante called it the “ring-shaped citadel”. Here you can steep yourself in the past and prepare yourself for the wonders of Siena
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Here your local guide will reveal to you its main…

What's Included
  • Professional guided tour of Siena (headsets not included in semi-independent option)
  • Free time to explore San Gimignano and Monteriggioni
  • Wine tasting experience at a Chianti estate (2-3 wines)
  • Sample regional products and extra-virgin olive oil
  • Travel in comfort with a fully-equipped GT Coach, including free Wifi
  • Assistance from an expert, multilingual Tour Leader
What's Not Included
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets (approx. 7€ pp)
  • Lunch
Additional Information

Experience a full day exploration of the prime attractions in Central Tuscany, complete with a delightful Chianti wine tasting. Traverse through the stunning rural scenery to your first stop, the radiant city of Siena, known for its unique square and Gothic-style town hall. Next, navigate towards San Gimignano, often referred to as the Medieval New…

Location
Piazzale Montelungo
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Cancellation Policy

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

Customer Ratings
4.5
(1749 Ratings)
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Raed_t
May 14, 2025
Amazing trip with lots of towns to see - One amazing trip. I can’t highly recommend this enough if you’re in Florence. The various towns are breathtaking and the history and sites are one of a kind.
Review provided by Viator
Yis489
May 14, 2025
Great value, good experience - Very helpful guides and good energy positive energy experience with Claudia and her male guide. Both were great and made the trip and cost very worthwhile
Review provided by Tripadvisor
Andreamarcelarr
May 13, 2025
Excellent trip through Chianti - The experience with the guides, the times in which we toured the cities of the tour were the best. All our expectations were met.
Review provided by Tripadvisor
Jan
May 13, 2025
The trip was excellent - a great way to see some of the beautiful countryside and historic cities in the area. - The trip was excellent - a great way to see some of the beautiful countryside and historic cities in the area. Monteriggioni, Siena and San Gimignano were all amazing. It was well organised and our guides, Anastasia and Marina were very good - so was our driver Raoul. The one downside for me personally, as a senior, was that there is a 10 - 20 minute walk uphill with the group from the coach park to the historic places and I struggled to keep up. Before I booked had a feeling that this might be an issue but the struggle was worth it. It did spoil the experience a bit for me. To finish the day off with the wine tasting was great and the wine was “medicine” for my aches and pains caused by all the day’s walking.
Review provided by Tripadvisor
Michelgoffard
May 13, 2025
Excellent 👌 - Very good tour, excellent organization, Raul and Anastasia excellent in their work, highly recommended, beautiful views from the bus to Tuscany and the tasting were very entertaining wines...
Review provided by Tripadvisor
F5695cdangelesg
May 11, 2025
Great trip - The trip has been fantastic, everything we have seen very nice. Very professional and friendly driver and guides provided us with a lot of information
Review provided by Tripadvisor
Carlafe686ki
May 11, 2025
An AMAZING tour - The tour was AMAZING, the scenery, the stops we made and the free time. All very well planned, our guide Giacoppo super friendly and attentive. I recommend it and would do it again.
Review provided by Tripadvisor
Maryann_l
May 10, 2025
A lovely day and well... - A lovely day and well worth the time. Around every corner a photo awaits! Siena is a very interesting city with a horse of a story waiting to be told! Our guide there was very proud of her city and the traditions it holds
Review provided by Viator
Richardgg4146qc
May 10, 2025
Brilliant Tour - Brilliant tour. Every stop was amazing. The wine tasting was especially good. The guides (Gabrielle & Gaia) were great, very knowledgable and funny.
Review provided by Tripadvisor
F9480feluciaf
May 11, 2025
A horror guide - Guide Roberto, it was really unbearable. He didn't stop talking for a minute. The tour was beautiful, but it is impossible to enjoy it with such a guide.
Review provided by Tripadvisor
From $73
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).