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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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Overview

Available languages

Portuguese
English
Italian
French
Spanish

10 hours 30 minutes

Mobile ticket

A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

Additional Info

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Infants are required to sit on an adult’s lap

Specialized infant seats are available

Not recommended for travelers with poor cardiovascular health

Travelers should have at least a moderate level of physical fitness

May be operated by a multi-lingual guide

Please note that the given order of the visits may change

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

Cancellation Policy

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

What To Expect

1

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.

45 minutes • Admission Not Applicable
2

Monteriggioni

After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).

1 hour • Admission Not Applicable

What‘s Included

Free time in San Gimignano and Monteriggioni Medieval towns

Gran Turismo Luxury bus travel with WiFi on board

Expert multilingual Tour Leader

Visit to a charming Chianti wine estate with tastings of up to 2-3 Chianti wines and regional snacks

Siena tour with professional guide with Headsets (not included in the "+ Free Time" option)

Gratuities

Hotel pickup and drop-off

Siena Cathedral tickets (approx. 7€ pp)

Lunch

Options

Spanish With Free Time

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Spanish With Guided Siena

All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Portuguese With Free Time

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Italian With Free Time

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Italian With Guided Siena

All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

English With Guided Siena

All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

French With Guided Siena

All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

English with Free Time

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

French With Free Time

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Portuguese With Guided Siena

All inclusive tour -Portuguese: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Reviews

4.60

2,572 reviews

Total reviews and rating from Viator & Tripadvisor

1909
433
141
43
46
  • What views! What wine! :)

    duncanc762,Mar 5, 2026

    - Review from Tripadvisor

    5.00

    A fantastic trip, highly recommended. Great views, great wine, fine food and i would certainly come again. Especially if not travelling alone. Did i say great wine? Jon was friendly and very helpful, open to questions and giving advice at all times. Laura was also very clear and full of interesting information throughout the guided tour of Sienna, before i had a very pleasant sociable lunch on the English speaker table from the group meal that was offered on the trip. Thank you Ciao Florence and thank you to Journee for booking my entire trip to include this :) Duncan

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  • Perfect experience in Siena tour

    R2711TT,Mar 5, 2026

    - Review from Tripadvisor

    5.00

    We had the best time in the Siena tour. John the guide was very nice and gave us great experience! The tour was built perfectly and we had the perfect time to every activity. Highly recommended.

  • Amazing day trip experience of Tuscany

    nataliekR6745ZA,Mar 5, 2026

    - Review from Tripadvisor

    5.00

    This day trip was amazing! Our guide Sara was very helpful and had a lot of humour, so it made our trip that much more enjoyable. We started by a visit of Monteriggioni which is a cute little (2 street) town with a lot of charm. We then arrived in Siena and as we had taken the guided tour we got a full and fun history lesson about the city. We then had free time to discover the city and one of the highlights was for sure the Cathedral of Santa Maria Assunta, which inside and out is absolutely breathtaking. There was also an option too eat lunch all together if we wanted too. We then continued our journey to Poggio al Laghi, a wine farm in the Chianti region know for their famous Chianti wine. The tasting was a very nice experience and the wines had such an amazing taste. We finished the day by having some free time in San Gimignano, which is a beautiful medieval town known for it's towers and has the gelato shop which is famous for being the best in the world. This was a must do experience if you come to Tuscany.

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  • Every stop was more...

    Kristin S,Mar 1, 2026

    - Review from Viator

    5.00

    Every stop was more magical than the last. Highly recommend this tour annd love all 3 stops. Our tour guide Constantino did an amazing job giving us the highlights of each location and keeping us on schedule. He had great tips on where to shop. Would definitely take another tour with him.

  • A must excursión around Florence

    Guzmanniembro,Feb 22, 2026

    - Review from Tripadvisor

    5.00

    Wonderful trip that everyone should do. Very comfortable and unforgettable thanks to Roberto (the driver) and Gabriele, who gave us tips and useful information to enjoy everything the most

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  • Great visit to the villages of Tuscany

    P8806QOmiguelf,Feb 22, 2026

    - Review from Tripadvisor

    5.00

    We really enjoyed the experience, the guides all very professional, both in Siena, Laura, and Roberto and Gabriele in general. A 10. Highly recommended.

  • 10/10 tour trip

    nadiadP7105XI,Feb 22, 2026

    - Review from Tripadvisor

    5.00

    We had an absolutely wonderful day tour from Florence to Siena, San Gimignano, Monteriggioni, and Chianti with Ciao Florence. Everything was perfectly organized from start to finish, and the entire experience exceeded our expectations. A special thank you to Gabriele, who was an incredible guide — knowledgeable, engaging, and genuinely passionate about the history and culture of Tuscany. He explained everything in such an interesting and easy-to-follow way, and she made sure everyone felt included and comfortable throughout the day. Also, a big shoutout to Roberto, our driver, who was fantastic. He navigated the Tuscan roads smoothly and safely, allowing us to relax and enjoy the stunning countryside views. His professionalism and calm driving made the trip even more enjoyable. The towns were breathtaking, the wine tasting in Chianti was a highlight, and the overall pace of the tour was just right — enough time to explore while still seeing so much in one day. I highly recommend this tour and especially hope you’re lucky enough to have Gabriele and Roberto as your team. Truly a memorable experience in Tuscany!

  • Excellent

    130giorgosm,Feb 22, 2026

    - Review from Tripadvisor

    5.00

    Very cool good driver Roberto

  • Good day in Tuscany

    Veronique M,Feb 22, 2026

    - Review from Tripadvisor

    4.00

    Great tour. Enough time at every place. Generous with tasting wine. Tour was bilingual English and Spanish. Roberto the driver was good and Gabriele the guide was also nice. Good value for Money. Book thru Booking and even got a last minute discount. Recommended.

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  • Amena excursion through Tuscany

    364pilim,Feb 22, 2026

    - Review from Tripadvisor

    5.00

    It has been a very good and beautiful experience, the guide Gabriele has been very good, pleasant and with a lot of humor has accompanied us all day. Driver Roberto drove smoothly.

-25% off

From €48.75

Was €65.00

4.60
(2,572 reviews)
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