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
(1587 Ratings)
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Cynthia_b
Oct 14, 2024
The best tour guide. - Enjoyed all of the tour especially San Gimignano and Sienna for the architecture and landscape. Our tour guide was amazing in both Spanish and English. She made the trip amazing for all of us!
Review provided by Viator
L8981tomichaelf
Oct 14, 2024
5 Start for Cecile and Giancarlo - Absolutely amazing! This was our first time ever doing one of these tours and we have no regrets. The stress of transportation, timing, where to go or what to do and see all disappears once you walk onboard. Cecile and Giancarlo were amazing! Professional, easy to deal with, funny and ensured we all ran on time. 5 starts for them both.
Review provided by Tripadvisor
Pintea
Oct 13, 2024
Gems of Tuscany - The staff was taken care of our needs and give interesting explanation about the places that we visited. Amazing team and organisation
Review provided by Tripadvisor
S6739ozclaudiaf
Oct 10, 2024
Excellent experience - It was a nice experience accompanied by Roberto as Guide We met Tuscan villages, I would recommend the company to make any tours
Review provided by Tripadvisor
Marioemidioo
Oct 10, 2024
TOUR TOSCANIA - The stay in San Gimignano should be longer. The tour team (Jimi and Roberto) were very friendly
Review provided by Tripadvisor
U6455ueivanm
Oct 10, 2024
It's worth the practical. - Very practical because they take you to several places that are very worth going, especially San Gimignano, without having to worry about car rental or loose transport. I have done less historical explanations and less explaining rules, menu and reminders. I think you can shorten this and focus on explaining even more curiosities. The tasting i San Gimignano the best.
Review provided by Tripadvisor
Tracied29
Oct 15, 2024
Good Experience - Despite the rainy weather we still enjoyed this tour. The stop in Monteriggioni was only 30 minutes. By the time you climb the hill and take a much needed bathroom break (with several other tour buses) there wasn’t much time to see the town. This was a disappointment. I would suggest extending the length of the tour to give people time to enjoy all of the stops. The stop in Siena was plenty long (2 hours) and we’re glad we opted for the half hour guided tour. The wine tasting was good. I don’t usually like wine and there was a red that I really enjoyed. My favorite part of the tour was the stop in San Gimignano. (1 hour) It’s a steep climb into town but totally worth it! Stunning views, even in overcast weather, and the town is just charming. It was a very long day but we’re glad we did it. Roberto our tour guide was very informative and kept us on schedule and Luca our driver did an excellent job.
Review provided by Tripadvisor
Karen_g
Oct 15, 2024
Very wet day - Yummy Gelato in San Gimignano. Unfortunately it absolutely poured with rain on the day of tour. We didnt realise eas forecast and were drenched. Best part of day was eating gelato.
Review provided by Viator
Marylou_t
Oct 14, 2024
Would recommend smaller tour group than bus tour due to problems with transportation to and from Viator meeting point. - Loved Sienna, wish more time could have been spent in San Gimignano. Guide was not as helpful as guide on the other bus traveling at the same time. Learned from friends on the other bus that their guide was more helpful with information. ALSO - while I understand that the tour employees at the meeting site were very busy, they could have been more courteous, and the meeting site was not conducive to getting taxi transportation back to hotels in Florence. Groups of people had to walk from bus station drop off to Train Station Taxi stand without direction or assistance from Viator.
Review provided by Viator
Lindsey_r
Oct 12, 2024
Good value, itinerary needs tweaked - Overall good value for a full day tour of Tuscany highlights with transportation! The only big change to the itinerary I would make is to axe the first stop Monteriggioni and devote more time to Siena & San Gimignano instead. Monteriggioni is super small to the point where it gets overwhelmed by such big bus tours dumping everyone off for an hour. The poor employees at the only two cafes in this town were visibly annoyed by the rush of bus people, and the stop didn’t have much to look at compared to the other stops. It was a glorified bathroom break. Meanwhile, at the end of the day in San Gimignano, we really wanted more time to linger in this super cute quintessentially Tuscan town, but we felt rushed by the 1.5hour time limit. Having 2.5-3 hours in SG would’ve been great.
Review provided by Viator
From $68
up to 15 guests
1 Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).