15 Best Siena & San Gimignano Day Trips In Florence

1-Day Tours, Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Tuscany Day Trips, Wine Tours

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

/ June 4, 2026

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

A full-day coach tour from Florence covering Siena, San Gimignano, Pisa, and Chianti winery lunch with wine tasting options.

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

/ June 4, 2026

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

A long-but-smart Tuscany day trip from Florence covering Pisa, Siena, San Gimignano, plus a Chianti winery lunch and wine tasting.

★ 4.6

“Highly recommend it! Best experience in Italy, totally worth the time and money. Siena is beautiful, the wine experience is unique, San Gimognano and Pisa are a must see!”

9,771 reviews12 - 12.5 hoursFrom $58by My Tour in Italy

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Chianti Wine Tours, Florence, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews

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

/ June 4, 2026

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

One day Tuscany hit list: Pisa’s tower, San Gimignano medieval streets, Chianti wine lunch, and guided Siena from Florence.

★ 4.5

“We had a great time with Sisilia and Guiseppe. Sisilia was super nice and gave us great suggestions for each of the stops. They were also very well timed. We had a great time and would strongly recommend it to all.”

8,393 reviews12 hoursFrom $52by Sightseeing Experience

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1-Day Tours, Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Florence day trip to Siena, San Gimignano, and Pisa with a Tuscan winery lunch and optional wine pairing, plus guided city highlights.

★ 4.5

“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.”

6,006 reviews12 hours (approx.)From $78.60by Ciao Florence Tours Srl

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Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

A full-day Tuscany trip from Florence with guided Siena, free time in San Gimignano, Pisa highlights, and optional Chianti lunch and wine tasting.

★ 4.8

“Sara was great! She was entertaining and knowledgeable. Our guide in Sienna was also incredible. She grew up there and lives there and knew all about local history and culture. 10/10!!!!”

4,538 reviews12 hoursFrom $112by Walkabout Tours

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1-Day Tours, Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Florence day trip to San Gimignano, Monteriggioni, Siena and Chianti, with lunch and a guided wine tasting.

★ 4.5

“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…”

4,432 reviews11 hours (approx.)From $83.27by CAF Tour and Travel

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Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Guided day trip from Florence to Pisa, San Gimignano, Chianti, and Siena, with optional lunch and wine pairing on an organized coach.

★ 4.6

“Very well organised from start to finish! Guides were brilliant, transport very comfortable, lunch was lovely and got to see some beautiful parts of Italy! A great day thank you!”

4,354 reviews12 hoursFrom $77by CAF Tour & Travel

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Florence, Food & Drink, Siena & San Gimignano Day Trips, Tour Reviews

Florence: Siena, San Gimignano & Monteriggioni with Tasting

/ June 4, 2026

8.Florence: Siena, San Gimignano & Monteriggioni with Tasting

A full-day Tuscany tour from Florence covering Siena, San Gimignano, and Monteriggioni, plus a Chianti tasting with regional snacks.

★ 4.6

“Our guide, Constantino, was very informative and made sure everyone in the group was well looked after. He also had a great sense of humour, which kept the tour enjoyable. The places we visited were all amazing. We had plenty of time in Siena, although a bit less in San Gimignano. It was quite a…”

3,218 reviews11 hoursFrom $46by Ciaoflorence Tours & Travel

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Chianti Wine Tours, Florence, Siena & San Gimignano Day Trips, Tour Reviews, Tours, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ June 4, 2026

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

Full-day Tuscany trip from Florence: UNESCO Siena and San Gimignano, medieval Monteriggioni, plus Chianti tastings and snacks. From $78.60.

★ 4.5

“Lovely full day of activities. Fun for families as you are driven by bus. However the private bus cannot stop at locations close to the old city gates so there is a large amount of walking up steep hills to get to town entrances. A public bus takes you right to the city entrances but…”

2,542 reviews10 hours 30 minutes (approx.)From $78.60by Ciao Florence Tours Srl

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Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

/ June 4, 2026

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

Florence to San Gimignano and Siena with Chianti lunch plus wine tasting, optional Siena Cathedral tickets, and UNESCO stops by air-conditioned bus.

★ 4.6

“We had the best trip! everything ran so smoothly, the guide was perfect thank you so much!”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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1-Day Tours, Chianti Wine Tours, Florence, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Tuscany Day Trips

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

/ June 4, 2026

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

One day from Florence to Pisa, Siena, San Gimignano and Chianti, with a guided Siena walk and a four-wine winery lunch tasting.

★ 5.0

“He was absolutely AMAZING! During our transport, he shared fascinating historical information and gave us fantastic recommendations for each city we visited. We loved his uplifting, high-energy personality—he was such a sweetheart to be around! And the wine… truly the best part! I would highly recommend this trip!”

2,283 reviews12 hours (approx.)From $78.60by CAF Tour and Travel

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Florence, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Tours

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

/ June 4, 2026

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

A small-group day trip from Florence to Siena and San Gimignano, with guided walking, free time, and a Tuscan winery lunch.

★ 5.0

“This was a great tour. Well timed with streamlined logistics, and plenty of free time in each town in addition to quick, informative tours. Lorenzo and Alex were a top notch team!”

1,675 reviews10 hours (approx.)From $180.19by Prestige Rent

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1-Day Tours, Florence, Siena & San Gimignano Day Trips, Tour Reviews

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

/ June 4, 2026

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

Florence day trip to San Gimignano and Siena via Chianti with a tour leader, big bus comfort, Wi‑Fi, and free time in both towns.

★ 4.7

“The tour was organized well and Sara, our guide and Giovanni, our driver gave a good day trip to San Gimignano and Siena. Sara provided information of each location before arrival and a WhatsApp message containing the audioguide, places to visit and map of the meeting point, which I appreciate since Siena is big and…”

1,624 reviews9 hoursFrom $71by TRAMVIA - Beducci Travel Bus

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1-Day Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews

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

/ June 4, 2026

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

Florence day trip to Pisa, San Gimignano and Siena with Chianti wine tasting and optional Siena Cathedral admission.

★ 4.5

“All of us in a group felt the same way toward this one tour leader. The staff wearing green & white were all accommodating with the exception of this one short long curly hair lady who was inconsiderate, impatient, rude and verbally abusive. She shouldn’t be representing Viator group. She was a big embarrassment to…”

1,108 reviews12 hours 15 minutes (approx.)From $59.13by myTour in Italy

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