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.

“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…”

3,762 reviewsFrom $164.26by My Tour in Italy

Check Availability →Read the review →

Florence: Siena, San Gimignano and Chianti Small Group Tour

Florence: Siena, San Gimignano and Chianti Small Group Tour - Siena’s Guided Walk, Cathedral Option, and the Palio Piazza

2.Florence: Siena, San Gimignano and Chianti Small Group Tour

★ 4.9

Small-group Tuscany day trip from Florence to Siena and San Gimignano with guided walk, Chianti wine tasting, lunch, and free time.

“We had a wonderful day trip to Siena and San Gimignano! Our guide Lorenzo was fantastic — knowledgeable, friendly, and passionate about the history and culture of Tuscany. He brought the medieval towns to life with fascinating stories and made sure everyone in the group was comfortable and engaged throughout the day. Our driver Sergio…”

433 reviews9 hoursFrom $175by Prestige Rent - Tours in Italy

Check Availability →Read the review →

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)

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

★ 4.6

One day from Siena to San Gimignano, Chianti and Montalcino with two winery tastings, Val d’Orcia views, and optional lunch.

“Amazing experience !! I loved every moment. High recommend this wine tasting tour. It was more than I expected and very memorable. From beginning to end, everything was just wow. We explored wonderful cities, got to taste some exquisite wines from the Chianti and Montalcino lands - both Chianti and Brunello wines were such a…”

195 reviewsFrom $158.60by My Luxury Drive

Check Availability →Read the review →

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

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.

“Great experience and easy way to get out of Florence for the day to see other areas of Tuscany. It was well organized even for a large group. Lunch was great with the wine tasting and seeing medieval villages was just amazing.”

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

Check Availability →Read the review →

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.

“Giovanni was great as a guide and driver. Air-conditioning in the van was brilliant. Beautiful places to see. The highlight was Poggio al Laghi winery with lunch. Brilliant! Very long day but worth it. Loved it”

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

Check Availability →Read the review →

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.

“Our guide Kiko was amazing ! Friendly polite and well versed in the history of the cities. Our tour which was a small group providing us with the opportunity of visiting small locations and meet people and experience things that we never would have been able to in a larger tour. Definitely worth the time!”

89 reviewsFrom $203.91by Tuscan Escapes by Papilio

Check Availability →Read the review →

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

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

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 a wonderful tour - the best we went on in Italy! Our guide was very knowledgeable and friendly, the wine tasting was wonderful, and the dinner was perfect. Highly recommend!”

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

Check Availability →Read the review →

Most recent

Explore Siena & Tuscany

Siena

Day Trips

Wine & Food

Experiences