Italy · SAN GIMIGNANO TOURS

The 15 San Gimignano Tours from Florence We Would Book First

24 tours  ·  from $46

Every trip has one free day too few. These 15 san gimignano tours justify the slot, priced and timed so the decision takes minutes and the rest of the day is yours.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - The Chianti winery lunch earns its place
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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Join Walkabout Florence Tours for an 11 to 12-hour coach trip through Tuscany. Guides such as Alex, Sara, Davide, and Manolo lead you through Siena, a Chianti winery, San Gimignano, and Pisa. Expect Siena Cathedral, free time, farmhouse food, four wines, and a fast-paced day with plenty of walking.

“Great experience all around and beautifully coordinated. Very unique. Manolo was the best tour guide ever!”

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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch - Starting from Florence and settling into the coach
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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch

2.Pisa, Siena and San Gimignano Day Trip with Lunch

★★★★★★★★★★4.6 · 9,771 reviews · 12 - 12.5 hours · from $58

Spend 12 to 12.5 hours exploring Tuscany by coach, with free time in Pisa and San Gimignano, an English guided walk in Siena, and a Chianti winery lunch. Guides such as Val, Luca, and Leonardo are praised for clear, friendly commentary, while the clean coach and careful timing keep this busy day manageable.

“Excellent day trip guided tour! Well planned, organized, explained, and executed. I highly recommend this tour!!!”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting the coach at Santa Maria Novella
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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

3.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52

Travel from Florence to Pisa, San Gimignano, Siena, and the Chianti Hills by Wi-Fi-equipped coach. Choose guided Siena, Leaning Tower access, and a winery lunch with tasting. Guides such as Barbara, Anna, and Lila add useful local context, while free time lets you explore on your own.

“Barbara was an amazing guide! She made an already amazing tour even better. Sienna was very nice. Poggio Al Laghi, the winery was very nice! Great cuts and cheese plate & a great pasta dish! The host was cool & funny. San Gimignano... what can I say.... ot was absolutely stunning & the highlight of the tour for us. It was quite, gorgeous, had midevil vibes and AMAZING views. It's one of those places that you want to move to for a few months after visiting. Pisa was overall forgettable. I highly recommend this tour!!!”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena begins with Piazza del Campo
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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

4.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Set out from Florence at 7:30 a.m. for Siena, San Gimignano, and Pisa. Choose the guided Siena visit and winery lunch with wine pairing, then enjoy free time in the hill towns. Guides such as Constantino, Sara, Jacopo, and Roberto have earned praise for clear timing and friendly help.

“Awesome, Enjoyed a lot , beautiful places, food is good , Tour guide is awesome, bus tour very nice, On time”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Meeting the coach near Santa Maria Novella
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

5.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Join Walkabout Tours from Florence for a 12-hour coach trip through Tuscany. Explore Siena with a local guide, taste four regional wines over a farmhouse lunch in Chianti, wander San Gimignano, and see Pisa’s Leaning Tower. Guides such as Alessandro, Sara, and Giancarlo are known for lively storytelling.

“What a day! Thank you Manolo for a wonderful day full of laughs and learning about the history of the Tuscany region. This was a great way to see so much of the beautiful Tuscan landscape and hospitality, topped off with a climb up the Leaning Tower of Pisa at sunset. Such great value for money, a must do!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Monteriggioni, a brief fortress stop
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

6.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Spend about 11 hours exploring three medieval Tuscan towns, a Chianti winery, and Siena Cathedral. You get round-trip coach transport, three wines, vin santo, and a three-course lunch. Guides such as Sandro, Ricardo, and Martha have earned warm praise, though the pace and group size can feel demanding.

“This was a great way to experience Tuscany if you only have a day. Comfortable bus, great locations and the included lunch/wine tasting was fantastic. Tour guide Sandro was very informative. My only recommendation would be to shorten the time in Siena - it seemed over long and made the day very long.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: brick streets and the Piazza del Campo
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

7.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Travel from Florence by air-conditioned minibus to Siena, a Chianti winery, and San Gimignano. You get guided context, free time, five wine tastings, olive oils, and a Tuscan meal. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and well timed.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.”

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Florence: Siena, San Gimignano & Monteriggioni with Tasting - Meeting at Piazza Montelungo
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Florence: Siena, San Gimignano & Monteriggioni with Tasting

8.Siena, San Gimignano & Monteriggioni with Tasting

★★★★★★★★★★4.6 · 3,218 reviews · 11 hours · from $46Best value

Spend 11 hours exploring three medieval Tuscan towns and a Chianti estate from Florence. Ride a Wi-Fi-equipped coach, hear live commentary in several languages, join a Siena walking tour if selected, and taste three local wines with homemade snacks.

“This was an amazing day trip. So much to see in just one day. Our tour guide John was very professional and knowledgeable. Would highly recommend as a day trip from Florence.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Siena, the main event
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

9.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Travel from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate in about 10.5 hours. Choose a guided or semi-independent Siena visit, taste two or three wines with snacks, and expect hills, a large coach, and a tightly timed day.

“I booked this tour with viator, but the tour was made with CIAO FLORENCE. It was the worst experiencie! We where in 13 people and when i bought It, It was informing that the vehicle hás 15 seats, but It was fone with a 60 seats bus, Full of people! I told to the representativos, but tbey Just ignored It!”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Pisa and the Field of Miracles
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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

10.Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78

Travel by air-conditioned coach from Florence to Pisa, San Gimignano, Siena, and the Chianti countryside. Expect a guided Siena walk, optional cathedral access, free time in each town, and a family-run winery lunch with four Tuscan wines when that option is selected. Guides may include Hilary, Sandro, Fabiana, or Alexandra.

“I signed up for English speaking but the tour was combined with Spanish speakers. I find people on the bus are rude (talking)while the tour guide speaks the other language. I think because the guide needs to speak in two languages, they cut short the information given. Also 50 people is too many for a tour that contains a lot of walking. Speaking of that, we spent about 20 minutes each way in each stop walking from to/from parking to tour beginning. That’s 2 hrs wasted! Tour guides need to speak slower while speaking in other languages.”

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Siena and San Gimignano: Small-Group Tour with Lunch from Florence - Meeting near Florence’s train station
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Siena and San Gimignano: Small-Group Tour with Lunch from Florence

11.Siena and San Gimignano: Small-Group Tour with Lunch from Florence

★★★★★★★★★★5.0 · 1,675 reviews · 10 hours (approx.) · from $180

Travel from Florence with an English-speaking guide and driver to Siena, Monteriggioni, a family-run winery, and San Gimignano. Expect a guided Siena walk, seasonal Tuscan lunch with wine, and free time for gelato, churches, and shopping.

“Lorenzo was a fantastic guide, perfect balance of information and leaving you to have free time to explore. Alex was a great driver. All round a lovely day that is highly recommended.”

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Florence: Day Trip with Free Time in San Gimignano and Siena - The ride through Chianti
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Florence: Day Trip with Free Time in San Gimignano and Siena

12.Day Trip with Free Time in San Gimignano and Siena

★★★★★★★★★★4.7 · 1,624 reviews · 9 hours · from $71

Travel from Florence to San Gimignano and Siena with a multilingual tour leader such as Sara, Sarah, or Alessandra, plus driver Giovanni on some departures. Enjoy roughly two and a half hours in each town, scenic Chianti views, Wi-Fi, charging ports, and a GPS audio guide.

“Sarah was great and we had plenty of time to explore both towns.”

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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch - Pisa and the Leaning Tower: a quick taste of the famous square
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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

13.Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

★★★★★★★★★★4.5 · 1,108 reviews · 12 hours 15 minutes (approx.) · from $59

Leave Florence at 7:45 a.m. for Pisa, San Gimignano, Siena, and a Chianti winery. You’ll have free time in Pisa and San Gimignano, a guided Siena walk, wine tasting, and an optional Tuscan lunch. Guides such as Niccolò, Marco, Alessia, and Luca are praised for clear stories and thoughtful help.

“It’s great experience . I have traveled with my mom . We saved time and nerves and enjoy this tour . Eduard was very kind.”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence - The Chianti Road and the first hour outside Florence
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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

14.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229

Travel from Florence by air-conditioned minibus along the Chianti Road, visit two wineries, taste at least eight Tuscan wines with local foods, and enjoy 1.5 hours in San Gimignano. Guides such as Emanuele, Valentina, Giovanni, and Ned bring regional stories to the drive.

“We had the best time on this tour. Our guide Giovanni was very knowledgeable about the wine and provided us with great history of Tuscany and the wines made here. All the wines we tasted were great.”

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Chianti Wineries Tour with Tuscan Lunch and San Gimignano - The first winery: personal contact and small-production character
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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

15.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Travel from Florence with a guide such as Lorenzo, Daniel, Christian, or Cecilia to two Chianti wineries, tasting several local wines and enjoying a Tuscan lunch. You’ll also have time in medieval San Gimignano and a photo stop above Florence. The group is limited to 16 people.

“Our guide Daniel was amazing. It was a lovely day at the wineries and touring San Gimignano. The wine was amazing and so were the snacks and lunch we were provided.”

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New in San Gimignano Tours

★ 4.5Siena & San Gimignano with Dinner in a Boutique WineryFrom $126199 reviews
★ 5.0Semi Private Deep Wine Chianti and San Gimignano from FlorenceFrom $252191 reviews
★ 4.6San Gimignano, Chianti & Montalcino Small-Group TourFrom $158195 reviews

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