Category Siena & San Gimignano Trips from Florence

Florence · SIENA & SAN GIMIGNANO TRIPS FROM FLORENCE

The 15 Best Siena & San Gimignano Trips from Florence

22 experiences compared

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

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Coach time to Siena: useful context before the first cobblestones

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 $114Editor's first choice

Florence day trip to Siena, San Gimignano and Pisa, with Siena Cathedral and a Chianti winery lunch plus wine tasting.

“Prob our least favorite excursion we have done this trip. Trip should be condensed to one stop (like Pisa) and maybe lunch/winery. However, our Tour guide was EXCELLENT. It’s just not the best trip we’ve ever done by far.”

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

Florence: Pisa, Siena and San Gimignano Day Trip with Lunch - Getting to Villa Costanza: The Tram Tip That Saves Time

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

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

A 12-hour Tuscany day trip from Florence to Siena, San Gimignano, Pisa, plus a Chianti winery lunch and wine tasting.

“I would recommend visiting San Gimignano first..we were too tired to enjoy and walk through the beautiful city. Our guide Alesseo was sweet and informative and our driver Michel was excellent!”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa and the Leaning Tower Tickets: What You See and What You Might Skip

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

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

One full day covering Pisa, San Gimignano, Siena, and Chianti wine tastings, with guided Siena and optional Leaning Tower tickets.

“The guide Anna was super nice and very resourceful, she gave very interesting insights and explained everything clearly. Sights were amazing and then wine tasting experience was exceptional.”

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

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Florence meeting point and why being early really matters

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

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

A 12-hour Florence day trip covering Siena, San Gimignano, and Pisa, with optional Tuscan lunch and wine pairing in the Chianti hills.

“Fabulous tour with guide Simone and Roberto. This was the best part of our trip. Thankful to see Pisa, Siena and San Gemignano was spectacular and the wine tasting with luncheon was very memorable.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena walking tour: Piazza del Campo, the Duomo, and the medieval details

5.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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

From Florence, tour Siena, San Gimignano, Pisa and a Chianti winery lunch with wine tasting, plus optional Leaning Tower entry.

“The tour was amazing! We had Alex as our tour guide and he did an incredible job. From the minute we drove out of Florence he spoke to the history of every city we visited and everything we saw on the way there. This was perfect as it gives context to what you’re seeing. Everything on the tour was very well thought out, we couldn’t be any more pleased with how everything went. I would strongly recommend 100%. Thank you Alex!”

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

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Stop 1: San Gimignano, the town of towers

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

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

Chianti day trip from Florence with San Gimignano, Monteriggioni, Siena, and a winery lunch plus wine tasting on an air-conditioned coach.

“This tour is a great way to see unesco towns with lots of history and charm in one day. It also included a light lunch which was only 2 courses not 3 as described and wine tasting which you can buy, if you don’t drink wine you get water.The guides Frederico Lillie and Fabbie were friendly and helpful. Overall an enjoyable day.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Meeting Piazzale Montelungo: The Part That Can Throw You Off

Florence: Siena, San Gimignano & Monteriggioni with Tasting

Florence: Siena, San Gimignano & Monteriggioni with Tasting - Monteriggioni’s Walled Hilltop: Short Stroll, Big Photo Value

8.Siena, San Gimignano & Monteriggioni with Tasting

★★★★★★★★★★4.6 · 3,218 reviews · 11 hours · from $46Strongest price

Florence to Siena day trip with Monteriggioni, San Gimignano, and a Chianti tasting. One coach, big views, 11 hours.

“We spent the day in good company... We're very lucky to have very nice people at the tour. The tour leader was fantastic and professional... A day well spent. I definitely recommend”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence

Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni Fortress: A Quick Stop With Great Photo Energy

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

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

Full-day Tuscany loop from Florence, with hilltop Monteriggioni, UNESCO Siena and San Gimignano, and a Chianti tasting with snacks.

“It was a good tour bit of a big tour but a very good tour.. You can miss the optional lunch which wasn't good at all and there are far better places to eat in Sienna. Also do take the optional Sienna tour which was very good.”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Meeting point in Florence: Piazzale Montelungo and the on-time rule

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Pisa, Field of Miracles: what you see in short windows

11.Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

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

A fast-paced Tuscany day trip from Florence to Pisa, Siena, San Gimignano and Chianti vineyards, with a winery lunch and 4-wine tasting.

“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

Siena and San Gimignano: Small-Group Tour with Lunch from Florence - Florence pickup and the ride to Tuscany: where the day starts smooth

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

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

Small-group day trip from Florence to Siena and San Gimignano with a guided walk, Tuscan winery lunch, and free time for tower views.

“We felt taken care of from the very start to being dropped off in Florence. Amazing way to see Siena , San Gimignano and the surrounding Tuscan countryside. Beautiful and fun day with incredible food and wine. We both loved it and would highly recommend to anyone. Lorenzo is a good host and very knowledgeable about the region all adding to the experience. Grazie Mille to Lorenzo and Tony for making it so memorable.”

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Florence: Day Trip with Free Time in San Gimignano and Siena

Florence: Day Trip with Free Time in San Gimignano and Siena - Meeting at Piazzale Montelungo, and getting the day started

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

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

Florence day trip to Chianti towns San Gimignano and Siena, with free time, expert leader, and scenic rides for $71 per person.

“This is a fabulous option if you want to visit these locations and want to have free time to explore. You will absolutely love San Gimignano ! Tour guides are very helpful and friendly ! If you leave from Florence bus station give yourself extra time to locate it.”

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

Florence Day Trip: Pisa, San Gimignano and Siena with Lunch - San Gimignano’s 14 Towers: Medieval Streets and Chianti Views

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

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

Pisa, San Gimignano, and Siena in one guided Tuscany day, with Chianti wine tasting and optional Siena Cathedral entry.

“My Tour of Italy was a beautiful 12 hour day that was a dream that came true as we went from place to place. It included a variety of touring, eating, sightseeing and enjoying free time in Tuscany!”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence - Stop 2 in Ulignano: Chianti and Super Tuscans meet a welcoming estate

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

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

Full-day Chianti wine tastings and San Gimignano from Florence, with two wineries, guided pours, and 1.5 hours to explore medieval towers.

“Valentina was fantastic!! Tour was amazing ! First winery was the BEST wine tasting I have ever been to !! Second one was very laid back . Town was adorable and gelato was delicious! Highly recommend this tour !!”

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