Florence · SAN GIMIGNANO DAY TRIPS FROM FLORENCE

San Gimignano from Florence: The 15 Best Days Among the Towers

34 tours  ·  from $46 a head

The towers are the photograph; the Vernaccia vineyards below are the lunch. The 15 below are compared on how long you get inside the walls and what else each day squeezes in.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - A Chianti farmhouse lunch worth lingering over
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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

Leave Florence by air-conditioned coach for Siena, where a local guide leads you through the medieval center and into its cathedral. Then visit a Chianti farmhouse for lunch and four wine tastings, followed by free time in San Gimignano and Pisa. The day runs about 11 to 12 hours; climbing the Leaning Tower requires a separate ticket upgrade.

“We had an absolutely incredible day with David as our guide! From the moment we met him, he made us feel so welcomed and at home, creating such a warm and fun atmosphere throughout the entire experience. Even with the rain, we truly enjoyed every stop! Siena, San Gimignano, the incredibly winery, and Pisa. Each place was breathtaking and made for an unforgettable day. The food and the wine were an absolute cherry on top! Chefs kiss Our small group was amazing, and we loved meeting people from all over the world who now feel like new friends. I would 100% recommend this tour to anyone, and I would happily…”

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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch - San Gimignano’s towers reward a slow walk
1-Day Tours, Day Trips from Florence, Florence Tours, Lunch Experiences, Pisa Day Trips from Florence, San Gimignano Day Trips from Florence, Siena Day Trips from Florence, Tour Reviews

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 seeing Tuscany’s best-known sights by coach: Siena’s medieval center, Pisa’s Piazza dei Miracoli, and San Gimignano’s towers. Depending on your option, lunch and Chianti wine tasting, an English guided walk in Siena, and cathedral entry are included. Guides on recent departures have included Val, Luca, Leonardo, and Fiama.

“Wonderful day. So much to see. Val our guide was excellent as was lunch and the wine..”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa: a short visit for the famous tower
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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 by Wi-Fi-equipped bus to Pisa, a Chianti winery, San Gimignano and Siena. Choose a light lunch and wine tasting, a guided walk in Siena, and Leaning Tower tickets. Guides such as Barbara, Anna and Layla share local context and practical tips, while the long drive between stops offers time to rest.

“Emma our your guide went above and beyond. Our experience was great and so worth it! We took my grandpa who is 80 years old and he loved it! We saw so much stuff in just one day!”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena: Piazza del Campo and the cathedral square
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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

Leave Florence at 7:30 am by air-conditioned coach for Siena, San Gimignano and Pisa. Depending on your selected option, you’ll have a local guide in Siena and a three-course winery lunch with wine pairing. Expect a full 12-hour day, free time in each town and plenty of walking.

“You get a great overview of many places in a single day. There is not a lot of time for in depth sightseeing but you get to many places. They pull it off flawlessly.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Lunch among the Chianti vines
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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

Travel by air-conditioned coach from Florence to Siena, a Chianti winery, San Gimignano and Pisa. A local guide leads the Siena walk, while you have free time at the other stops. Choose the farmhouse lunch and four-wine tasting, and check your option carefully if you want a Leaning Tower ticket. Guides vary, with Sara, Alessandro and Manolo among those who lead departures.

“It was great and perfect. Tour guide was super good, fun and friendly. Making everyone feel welcome and the tour enjoyable! 1000% to join this tour!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: towers, lanes, and a short window
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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

Leave Florence by coach for San Gimignano, Monteriggioni (April to October), a Chianti winery lunch and tasting, and Siena. Expect free time in the towns, with a Siena walking tour and cathedral entry available only on selected options. Guide teams vary; past departures have included Sandro, Ricardo, Marta and Ilaria.

“Other reviews are correct- this is not a guided tour. However, I liked how we are on our own in each city rather than having to keep up with a guide and large group. Hilary was very sweet and gave us information about each city before exiting the bus. The winery was just a tasting experience (4 wines) with lunch. I thought they gave us a lot of food: bruschetta, meats, cheese, a full portion of pasta with ragu, and biscotti. Personally I was full after it. The employees there were very energetic and fun. Be prepared for a lot of walking. Uneven streets and hills. This tour is not…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa: the Field of Miracles in 80 minutes
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

7.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

Travel by air-conditioned coach from Florence to Pisa, San Gimignano and Siena, with a scenic drive through Chianti. You get free time in each town, plus an optional lunch with three wines and Vin Santo. A Siena guide and cathedral entry are included only with selected options.

“Love our guide, Santo! And Paul at Siena! Very professional and informative.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: a quick look at a remarkable city
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

8.San Gimignano, Siena, and Chianti Wine Tour

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

Leave Florence by air-conditioned bus or minivan for Siena, a Chianti estate, and San Gimignano. You get free time in both towns, a guided winery visit, five wine tastings, and a Tuscan meal featuring truffle lasagna, cheeses, cured meats, and more. Guides have included Marco, Lyla, and Marta, though assignments vary.

“Great experience, Lyla was a great guide. Very well coordinated and overall very fun!”

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Florence: Siena, San Gimignano & Monteriggioni with Tasting - Monteriggioni: a small village behind old walls
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Florence: Siena, San Gimignano & Monteriggioni with Tasting

9.Siena, San Gimignano & Monteriggioni with Tasting

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

Ride an air-conditioned coach from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate for three local wines and regional snacks. You get free time in the medieval towns, with an optional guided Siena tour. Guides vary, with Alex, Constantino, and John among those who have led recent trips.

“Leo was a very knowledgeable tour guide. He set high expectations for our tour and as a result it was successful. The trip was nicely paced out. The tour ended with a wonderful Chianti wine tasting.Mario was an expert driver. We felt very safe. Thank you!”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni: a compact first taste of medieval Tuscany
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

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

Ride from Florence through central Tuscany to hilltop Monteriggioni, Siena and San Gimignano. The Classic option adds a guided Siena walk; the Semi-Independent option gives you more time to explore alone. Finish with a tasting of up to three Chianti wines and regional snacks. Expect a long day, shared coach and plenty of walking.

“Nice Tuscany day tour. Alex was great in explaining about the various areas we visited, and the driver Cozimo did a good job getting us back safe.”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Lunch and wine in the Chianti hills
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

11.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel by air-conditioned bus from Florence to San Gimignano, Siena and the Chianti hills, with a multilingual escort and free time in the towns. A winery stop pairs a Tuscan-style lunch with a guided tasting of three wines. Add a local Siena guide and Cathedral entry if you want a closer look at the city’s landmarks.

“Hilary led us through a well organised and informative tour of Tuscany. The towns were beautiful and the lunch experience excellent.”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - A winery lunch that breaks up the bus-and-monument rhythm
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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

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

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

Leave Florence at 7:30 am by air-conditioned coach for a full day among Tuscany’s best-known towns. Expect a guided walk in Siena, free time in San Gimignano and Pisa, and, on qualifying options, a winery lunch with four wine tastings. The Leaning Tower is a photo stop, not an included climb.

“I definitely recommend this trip! Sienna and Gimignano were amazing. Pisa was more of just a picture opportunity, but happy we got to see it as well.”

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Siena and San Gimignano: Small-Group Tour with Lunch from Florence - Siena: a guided walk through the medieval center
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Siena and San Gimignano: Small-Group Tour with Lunch from Florence

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

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

Leave Florence at 8 a.m. for Siena, a family-run winery, and San Gimignano, returning around 6 p.m. You’ll get a guided walk in Siena, a cellar visit and seasonal lunch with wine, then free time among San Gimignano’s medieval towers. Guides such as Lorenzo and Susie have led the route; the group can include up to 25 people.

“Wonderful experience! The tour ran very punctually. There was the right balance of speaking and quiet time. Lorenzo was friendly and a pleasure to have as a tour guide.”

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Florence: Day Trip with Free Time in San Gimignano and Siena - First stop: San Gimignano’s medieval skyline
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Florence: Day Trip with Free Time in San Gimignano and Siena

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

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

Ride from Florence to medieval San Gimignano and Gothic Siena, with about two and a half hours to explore each on your own. A multilingual tour leader such as Sara or Alessandra shares pointers, and a GPS audio guide helps you plan your visit. The bus has Wi-Fi; entrance tickets and meals are extra.

“Sarah was a great guide. We had a good amount if time in both cities to explore”

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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch - San Gimignano: towers, lanes and a slower mood
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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

15.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 am by coach for Pisa, San Gimignano, a Chianti winery and Siena. Expect a full 12-hour day, plenty of walking, free time in the towns and an English-speaking guide in Siena. Lunch and Siena Cathedral admission depend on the option you book.

“This tour was definitely by far one of the best tours we have ever done! Every single part of it went better than I could have imagined. Our tour guide Niccolo was amazing! He was so informative, yet personable and funny. He did such a great job as our guide, telling us of different legend and stories that exist around Italy. The tour was also great! My favorite part was definitely the wine tasting. My husband and I will always remember this as a core part of our trip to Florence.”

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