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

“This trip is a great value. So much so that I was concerned it couldn’t possible meet the expectation. However, the day was fantastic. Our guide Val was so informative and funny and helpful! The bus was so clean and so comfortable. You can leave your belongings on the bus, so bringing an umbrella or…”

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

“This excursion was incredible. I went with my family and it exceeded our expectations. 12 hours seems long, but it really doesn’t feel like 12 hours because you get a chance to rest in the bus between places. It was one of the best days of our 10-day trip and definitely worth the price!”

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

“Tour has a little too much walking and too long 12 hrs. It would be better if you offered a package without Pisa. Didn't appreciate the cash grab at the end. At Pisa, we were told it was a long walk from bus parking to Pisa tower and not recommended we walk. If we wanted…”

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 informational and warm. Our guide in Sienna was helpful to understanding the local art and history. Enjoyed the friendly rivalry between Florence and Sienna. While we felt hurried, each stop was just the right amount of time. Each site felt like a day unto itself.”

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

“Lovely informative day to see a slice of Tuscany. Our guides were great and the bus very comfortable. Met some lovely people also. Would recommend this tour.”

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

“Best tour we had in Italy. Well planned saw a lot with plenty of rest. Very happy”

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

“Very beautiful countryside and stops. Bus driver Mario did an excellent job and Alex was very informative and did an excellent job as well. Thank you for a great tour!! Will recommend GYG to friends and relatives!”

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

“Constantino, Anastacia were great! We missed the bus in the morning but caught up with the group in Siena they waited for us and welcomed us to the group! We had a great time they are a blast!”

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

“It was a great trip. Sara and Placido made our day go very smooth. The towns beautiful and the wine & lunch just perfect, by the way, you also taste olive oils and balsamic vinegar. I recommend this.”

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

“It was amazing, the people were friendly and funny and the sites were beautiful 😍 it was a bit hot but besides that, great day 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

“Very enjoyable experience with professional tour guides. Really a perfect day with low stress and good pace.”

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

“This was a prefect and comfortable way to explore 2 cities from Florence. Very comfortable bus, lots of free time to explore these beautiful places on our own and the perfect amount of time in each. Before each stop we were sent a lot of information on What’s App with sites to visit if we…”

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

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