San Gimignano Day Trips

TUSCANY · DESTINATION

10 Best San Gimignano Day Trips From Siena

Most booked first.

The 10 most popular day trips to San Gimignano from Siena. The medieval towers, the Vernaccia tasting, the walk through Tuscany’s most photographed skyline — what works as a guided half-day and what you save for an overnight.

10 Best San Gimignano Day Trips From Siena

From Florence: San Gimignano, Siena, and Chianti Wine Tour

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Starting point in Florence: meet near the Baptistery

1.From Florence: San Gimignano, Siena, and Chianti Wine Tour

Most Popular★ 4.5

Florence to Siena, San Gimignano, and Chianti in one full day with guided history, five wine tastings, and a Tuscan lunch.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

3,762 reviewsFrom $164.26by My Tour in Italy

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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - A small-group van with a bilingual escort (and why that helps)

Small-Group San Gimignano and Volterra Day Trip from Siena

Small-Group San Gimignano and Volterra Day Trip from Siena - Monteriggioni’s walls: why this hill town is a smart warm-up

4.Small-Group San Gimignano and Volterra Day Trip from Siena

★ 5.0

A small-group day trip from Siena to San Gimignano and Volterra, with Via Francigena walks, saffron farm lunch, and alabaster craft.

“Excellent tour. The highlight was a visit to a workshop to meet Orme and watch him work alabaster by hand. We then had the opportunity to purchase his beautiful pieces. Our guide was first rate.”

180 reviews8 hours (approx.)From $217.77by Tuscan Escapes by Papilio SRL

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San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting - Florence to the First Stop: A Day That Starts Early

5.San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

★ 4.5

A full-day escorted tour from Florence featuring San Gimignano, Monteriggioni, Siena, and a Chianti winery lunch with wine tasting.

“Martha was the host, she was great! She always had lots of info for each place we visited. Such nice towns we visited. Love the area! Would recommend the tour.”

171 reviews11 hours (approx.)From $95.58by CAF Tour and Travel

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena - Price and time: 11 hours, and why the early start matters

6.San Gimignano, Chianti, and Montalcino Day Trip from Siena

★ 4.5

An 11-hour Siena day trip hitting San Gimignano, Chianti wine country, and Montalcino for Brunello tastings plus classic Tuscan stops.

“Buyer Beware. This tour was a 3rd party vendor My tour 366, who rescheduled the tour and overbooked what was supposed to be an 8-12 semi-private tour to 28 people. The two wineries were not able to accommodate. we ended up in the production area at the last minute, not the tasting room. The bus…”

150 reviews11 hours (approx.)From $168.96by myTour in Italy

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San Gimignano and Volterra: Day Tour from Siena

San Gimignano and Volterra: Day Tour from Siena - Getting going: meeting at San Domenico Basilica (and no hotel pickup)

7.San Gimignano and Volterra: Day Tour from Siena

★ 4.8

Small-group day trip from Siena to San Gimignano and Volterra. Monteriggioni stop, alabaster workshop, saffron lunch, Vernaccia wine.

“Loved the locations. The van had eight plus the driver. It felt crowded. The vineyard provided an excellent lunch. Loved the scenery everywhere. Cool old cities.”

89 reviewsFrom $203.91by Tuscan Escapes by Papilio

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Chianti and San Gimignano – 2 Wineries with Pairing Lunch

Chianti and San Gimignano - 2 Wineries with Pairing Lunch - San Gimignano’s medieval center in one hour: towers, gelato, and quick orientation

8.Chianti and San Gimignano – 2 Wineries with Pairing Lunch

★ 5.0

Two Chianti tastings and a wine-paired lunch, plus medieval San Gimignano, with round-trip pickup from Siena or Florence.

“What a wonderful and unforgettable day in Tuscany. Stefan picked us up near our hotel in Siena in his spacious, comfortable van and with two other couples set out on a day we will not soon, if ever forget.”

70 reviewsFrom $423.77by Forzoni Tours

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From Siena: Chianti and San Gimignano Sunset Tour

From Siena: Chianti and San Gimignano Sunset Tour - Monteriggioni’s fortress walls: short time, big wow factor

9.From Siena: Chianti and San Gimignano Sunset Tour

★ 4.8

Small-group Chianti winery tasting, Monteriggioni fortress, and San Gimignano sunset, finished with Vernaccia or Chianti at a farm dinner.

“Guillermo was an absolutely fantastic guide! His knowledge of the history was impressive, and he brought each story to life in a way that made the experience truly unforgettable. He was also incredibly attentive to all of us, ensuring everyone felt comfortable and engaged throughout the tour. I can't recommend Guillermo highly enough—if you're looking…”

67 reviewsFrom $203.91by Tuscan Escapes by Papilio

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Small-Group Chianti and San Gimignano Sunset Trip from Siena

Small-Group Chianti and San Gimignano Sunset Trip from Siena - Monteriggioni stop: the fortress-town walls you can still walk around

10.Small-Group Chianti and San Gimignano Sunset Trip from Siena

★ 5.0

Small-group Chianti and San Gimignano sunset trip from Siena with wine tastings, Monteriggioni walls, and a farm dinner with sunset views.

“This was an amazing excursion! It was worth every penny! The tour itself was so informative and fun. The food and wine were great and it’s just the right size group. Highly recommend!”

63 reviews8 to 9 hours (approx.)From $217.23by Tuscan Escapes by Papilio SRL

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