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
(1621 Ratings)
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Marileen_s
Mar 4, 2025
Good as far as bus tours go - Good experience. It is nothing more or less it advertises itself to be. You'll see some wonderful places and I could tell they really worked on some of the things other reviews complained about. For instance they gave us more free time in Siena and San Gimignano and they also helped people navigate to the taxis afterwards. If you're in the same position that I was, wanting to see more but not being able to rent a car, I would definitely suggest this tour. San Gimignano is worth it on its own.
Review provided by Viator
Hgrivel
Mar 3, 2025
Don't miss this trip if you are Florence - If you are in Florence. You should not miss this trip. Sienna stole the show! Didn't expect such a beautiful city, Wine testing was great and very entertaining.
Review provided by Tripadvisor
Safari28795772978
Feb 21, 2025
An unforgettable experience! - Had a brilliant time. Fantastic well run tour. Tour guide Constantino and driver Aldo were very good. Constantino was clear with instructions about meeting points and had great recommendations on what to see from everywhere we visited. We also loved the wine tasting opportunity at the vineyard, it was very special. Such good value for the full day of opportunities and new places to see. A great end to our Florence trip.
Review provided by Tripadvisor
417billyb
Feb 20, 2025
Great day in Tuscany - Everything that they said it would be. Great day with, with great towns, and very good wine. Would highly recommended it.
Review provided by Tripadvisor
Paulinev972
Feb 20, 2025
Excellent day - On this day of February 20th accompanied by Aldo the driver and Roberto our guide we were able to discover a small part of Tuscany. We highly recommend this nice course full of discoveries.
Review provided by Tripadvisor
Emily
Jan 19, 2025
Surprise Highlight - Tabitha (guide) and Luca (driver) were fantastic! This was the unexpected highlight of our visit. Definitely recommend doing the longer trip so you have more time to check out each of the towns. Our local guide in Siena was also fantastic.
Review provided by Tripadvisor
X3121wwwilliamc
Feb 19, 2025
Wine tasting is really a forced sales pitch for a crappy, non-traditional vineyard. - This was a good way to see a few of the hill towns in one day from Florence. I would not recommend the guided tour or lunch option. Italy has too much good food to waste a meal here eating tourist food. You will walk by much better places to eat in Siena. The wine tasting was a waste of time, and it made the trip too long, as well as taking away from time that could have been better spent in San Gimignano. The “wine tasting” was more of a forced sales pitch, and the wine was not even good. The traditional wine in Italy is top tier, but this particular winery is trying to make new versions of wine that are an insult to good Italian wine. They decided to invent a version of balsamic vinegar without grapes, so they used onions instead. It was some of the most offensive garbage I ever tasted, and the wines followed a similar mentality.
Review provided by Tripadvisor
A2zstyle
Jan 28, 2025
Correct and recommended - Comfortable trip by modern minibus, just enough time to take a look at Monteriggioni and San Gimignano. Guide in Siena professional and enjoyable, with enough free time if you do not reserve food. The wine tasting very correct although there is time for the rest of the visits. Recommended.
Review provided by Tripadvisor
Christine_s
Feb 18, 2025
Not for the infirm as lots of fast walking - Crams a lot into one day, so good value. The guide gave a lot of information but gave the impression of being bored. It was a large group and she walked very fast so 4 of us couldn’t keep up and nearly got lost several times. Her attitude was ‘tough’ when we asked her to slow down. This would have been even worse in high season in Siena with more crowds.
Review provided by Viator
Dorcas_f
Feb 27, 2025
Bus tour guide was unhelpful, uninterested and a poor communicator. - I have some difficulty walking and walk with a cane, so I did not plan to visit Montereggiano. I spoke to the tour guide about this and she indicated that Siena was flat, implying that I would not have a problem. However, she did not mention how far I would be expected to walk in Siena to get from the bus parking lot to the restaurant. My friend and II walked as fast as we could but got further and further behind. The tour guide said she sent someone to look for us but could not find us. Essentially, she abandoned us. Luckily, I had my iPhone with GPS navigation, so we were able to walk to the restaurant, arriving way to late to explore Siena. If I had not had the I-phone with navigation, we would have been totally lost and abandoned in Siena and had a major problem. The tour guide had no way of knowing that we had this technical help. After lunch, we asked the tour guide to speak to a taxi driver and give instructions to get us back to the bus parking lot. This worked well and we think the tour guide should have been more proactive and suggested and called for a taxi from the bus parking lot to the restaurant. She also should have suggested the taxi back to the bus. Bottom line, we did not see any of Sienna. After we returned to Florence, the guide indicated that we could walk from the bus drop-off area to SMN station. We told the guide that the distance is too far for me to walk, and the guide should have known this based on the experience in Siena. When asked, she refused to call a taxi for us. Bottom line, the guide was a major disappointment, and the result was that we did not see the cathedral in Siena, our main goal for this tour. Bottom line: this major disappointment could have been prevented if the guide had suggested and arranged for taxis from the bus parking area to the restaurant and back. As a general principal, we think that if the bus cannot let us off at the the venue, this should be detailed in the trip description with the length and level of difficulty of the walk so that potential clients can judge whether or not the tour is suitable for them.
Review provided by Viator
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up to 15 guests
1 Adult
March 2025
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