Tuscany Day Tour: Explore Medieval Siena, San Gimignano, Monteriggioni with Chianti Wine Tasting
4.4
1,211 Ratings
Firenze
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: 1 day learn more
Highlights
  • Florence - There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
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 York, and Monteriggioni, a castle perched atop a hill offering panoramic views. No trip would be complete without a stop at a Chianti winery where the finest Italian wines are waiting to tantalize your taste buds. It’s an ideal day out to unwind and rejuvenate your senses.

  • A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
  • May be operated by a multi-lingual guide
  • Please note that the given order of the visits may change
  • Please inform us of any food intolerance or allergy in advance
  • Kindly note that the Semi independent option does not include the professional guide in Siena
  • LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
  • HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
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
4.4
(1211 Ratings)
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U9837vlrachelb
Jun 6, 2024
10/10! - What a wonderful way to spend your day! It’s a long day but if you want to learn the history of the Tuscan people and their culture it’s worth every minute. I couldn’t be happier with how the day went! Sara our tour guide was amazing. She was extremely thoughtful and considerate of everyone on the trip and gave great information on our drives to and from places. You also get a reasonable amount of time at each stop to do some shopping or sightseeing which i really appreciated. All in all it was a 10/10!
Review provided by Tripadvisor
H7486fmmichelep
Jun 6, 2024
Would recommend - Sara was a very friendly, kind, and helpful guide. This tour was a great and easy way to see more of Tuscany in a day without having to worry about getting around. My friend and I had a lot of fun.
Review provided by Tripadvisor
Hunter
Jun 6, 2024
Hidden Tuscan Gems - Great way to see more of Tuscany away from the noise and bustle of Florence. Beautiful stops with time to shop and a lovely wine tasting at a true Tuscan vineyard!
Review provided by Tripadvisor
Vicki
Jun 6, 2024
Great value for money - I was impressed with the slick organisation of this day trip. Our guide Roberto did an excellent job of keeping 50+ people informed, ensuring everything was clear and went smoothly and he did this in two languages. Impressive. It was a fun day with entertaining tour guide in sienna and an hilarious wine tasting in chianti. Also a big thank you to Luigi for his safe and careful driving. Overall a great day out and excellent value for money.
Review provided by Tripadvisor
Terri_f
Jun 2, 2024
Fantastic day out - Fantastic day! Great way to see Tuscany if having a short stay. Good value for money. Roberta was excellent as a host. Luigi a great driver.
Review provided by Viator
Samgrey288
Jun 2, 2024
An excellent day trip from Florence - Roberto was an excellent guide. He was very informative and made the day really fun. The tour ran very smoothly and we felt like we had the perfect amount of time in each town. The wine tasting was also great! Would highly recommend this day tour from Florence
Review provided by Tripadvisor
Terry
Jun 1, 2024
10 out of 10 - The Tuscany medievil gems tour was spectacular. The tour guide Roberto was amazing , very friendly and informative. Highly recommend taking this tour.
Review provided by Tripadvisor
Dawnpt1277bx
Jun 1, 2024
A Great Day Exploring Cities Beyond Florence - We had a wonderful day exploring Monteriggioni, Siena, Chianti Wine Region, and San Gimigano. Our tour director was Roberto and our driver, Luigi. Both made the day extremely enjoyable for us. It was the highlight of our vacation thus far. Roberto did a great job describing each of our stops and gave us a good deal of background information prior to each stop. We felt completely transported back in time to these medieval cities. Each seemed more beautiful than the next. The tour provided the appropriate amount of time at each location. Luigi did a great job transporting us safely via coach bus to each location. We would highly recommend this trip to anyone who would like to expand their visit to Florence. Thanks for a great day!
Review provided by Tripadvisor
Mary_b
May 31, 2024
Good way to see Tuscany in a day. - This was a good way to see a lot of Tuscany in a day. There was just enough time at each stop. Our guide Gabriele was great and the group was on time, which other people said could be a problem. We did not do the tour with the group in Sienna. We did a Rick Steves audio guide walking tour and the timing was great. I had bought (in advance) a timed entrance to the duomo for the walk around the top of the church to get a good view of the mosaics on the floor. The time was for 1 and it worked out well. An entrance for anytime between 12 and 1 would have worked. All in all a nice day. The stop at the winery was a nice little event. It was nice for my mom who is 75. There is a lot of walking but it is nice the bus gets you pretty close to each point of interest.
Review provided by Viator
Travelka7
May 30, 2024
A wonderful introduction to Tuscany - Our tour with Ciao Florence was a win! Gabrielle (our guide) and Michaele (driver) made us feel welcome, well taken care of and entertained :). We really enjoyed visiting Siena and San Gimighano: Siena cathedral was a true gem (try to go inside - it’s really beautiful, more so than outside, reserving the ticket in advance would help) and the scenic views in San Gimignano were classic picturesque Tuscany at its best. Don’t underestimate a few shopping opportunities in that last stop - lots of local high quality fare with more reasonable prices. The wine tasting was fun thanks to the great host; the 20 year old balsamic vinegar was surprisingly flavorful. Monteriggioni (first stop) was forgettable, could have skipped it easily in favor of more time at the other places. Thank you Gabrielle for taking special care of our family when we were a bit late for lunch! We really enjoyed this tour, you made it special!
Review provided by Tripadvisor
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June 2024
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