15 Best Siena & San Gimignano Tours In Florence

1-Day Tours, Florence, Lunch Experiences, Pisa Day Trips, Siena & San Gimignano Tours, Tour Reviews, Tuscan Countryside Tours, Wine Tours

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

/ June 1, 2026

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

A full Tuscany day trip from Florence with guided Siena, towers of San Gimignano, Pisa highlights, and Chianti winery lunch plus a wine tasting.

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

/ June 1, 2026

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

Guided day trip from Florence to Pisa, Siena, and San Gimignano with Chianti lunch and wine tasting—packed but well paced.

★ 4.6

“Our tour guide, Leonardo, was amazing! He was kind and passionate. He shared interesting facts about the places we visited. It was great value for money since we saw many different places all in one day.”

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

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

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

/ June 1, 2026

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

Florence day trip to Pisa, San Gimignano, Siena, and Chianti with free time, optional Siena guiding, and optional Leaning Tower tickets plus wine.

★ 4.5

“The trip was well organized and the guide was excellent in her duty. The trip was worth the money”

8,393 reviews12 hoursFrom $52by Sightseeing Experience

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

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

/ June 1, 2026

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

Florence day trip: Siena, San Gimignano & Pisa, plus winery lunch with wine pairing. Coach tour, free time, Wi‑Fi.

★ 4.5

“It is a wonderful tour and the price is reasonable.”

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

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

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

/ June 1, 2026

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

From Florence: Siena, San Gimignano, Chianti winery lunch, and Pisa in 12 hours. Guided sights, wine tasting, optional tower entry.

★ 4.8

“Our trip was excellent and my friends and I really enjoyed our day. The guide was brilliant with so much knowledge of the areas we visited and really made our trip special. We loved seeing the Tuscan countryside and towns we visited.”

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 Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

San Gimignano towers, Chianti winery lunch and wine tasting, and Siena’s Duomo and Campo—an 11-hour coach day from Florence.

★ 4.5

“It feels very rushed in last portion of tour. We had a guide that walked entirely too fast and our chronic knee and back pain were exacerbated trying to keeep up. Guided tour wasn’t really necessary… save yourself the expense. Meal was delicious! We thoroughly enjoyed San Giiagmano wish it was longest stay of tour.”

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

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

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

/ June 1, 2026

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

Florence day trip to Pisa, San Gimignano, Chianti and Siena. Leaning Tower views, UNESCO towers, guided Siena, optional lunch+wine.

★ 4.6

“This tour is worth every penny, it’s an entire day of visiting beautiful places and making memories. Our guide Sandro is very knowledgeable and friendly”

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

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Florence, Food & Drink, Siena & San Gimignano Tours, Tour Reviews

Florence: Siena, San Gimignano & Monteriggioni with Tasting

/ June 1, 2026

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

Florence day trip to Siena, San Gimignano, and Monteriggioni plus a Chianti tasting at a local estate with 3 wines and snacks.

★ 4.6

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

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

Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ June 1, 2026

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

See UNESCO Siena and San Gimignano plus Chianti wine tasting on a full-day coach tour from Florence with guided stops and free time.

★ 4.5

“Sara and Lorenza were great tour guides. Mario a safe bus driver. Bus was comfortable. Knowledgeable professional and most pleasant”

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 Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

Florence day trip to San Gimignano, Siena and Chianti: UNESCO towns, optional cathedral visit, and lunch with a three-wine tasting.

★ 4.6

“Sarah was a really knowledgeable guide and answered all of our many questions very patiently. The driver (I cannot remember his name, sorry), was very safe and conscientious. Good value!”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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1-Day Tours, Chianti Wine Tours, Florence, Pisa Day Trips, Siena & San Gimignano Tours, Tour Reviews, Tuscan Countryside Tours

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

/ June 1, 2026

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

One day from Florence to Pisa, Siena, San Gimignano, and Chianti wine. Guided walks, a winery lunch, and iconic sights at a steady pace.

★ 5.0

“What a fun day! We saw so much and learned a great deal. He made sure he got his to Pisa early so that we could beat the crowds, and that was a very good thing. The wine tasting and food were phenomenal. Every step was interesting, informative, and exactly the right amount of time.…”

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

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

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

/ June 1, 2026

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

Guided Siena and free-time San Gimignano from Florence, plus a Tuscan winery lunch with wine, tastings, and views.

★ 5.0

“This tour experience was exceptional! It was well organized with a kind, informative guide, Lorenzo, who truly has a passion for Florence. Our tour bus driver also supported us well and got us to our different destinations with no issues.”

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

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

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

/ June 1, 2026

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

Florence day trip to San Gimignano and Siena with guided orientation, free time in both towns, and Chianti countryside views.

★ 4.7

“An outstanding tour experience. The guide was extremely kind, professional, and highly knowledgeable, providing clear and engaging explanations throughout. The timing at each location was perfectly planned, allowing us to fully enjoy every stop without feeling rushed. The driver was very skilled and made the journey comfortable and safe. Overall, a wonderful experience that I…”

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

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

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

/ June 1, 2026

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

Florence day trip to Pisa, San Gimignano and Siena with a Chianti winery lunch and wine, guided in English from 7:45am.

★ 4.5

“This tour was definitely by far one of the best tours we have ever done! Every single part of it went better than I could have imagined. Our tour guide Niccolo was amazing! He was so informative, yet personable and funny. He did such a great job as our guide, telling us of different legend…”

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

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Florence, Siena & San Gimignano Tours, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Wine Tours

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

/ June 1, 2026

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

Florence Chianti road day trip with tastings at 2 wineries, Vernaccia near San Gimignano, plus 1.5 hours to wander towers and medieval streets.

★ 5.0

“The communication, and experience as a whole was excellent. Emanuele was superb and the two different wine experiences made it even more enjoyable. The views, amazing and finishing off at San Gimignano was a delight being able to have some free time to venture out.”

1,007 reviews7 hours (approx.)From $229.77by Italy on a Budget tours

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