Florence · SIENA AND SAN GIMIGNANO DAY TRIPS

The 15 Best Siena & San Gimignano Day Trips

23 tours  ·  from $46

A shell-shaped square, a striped cathedral and fourteen surviving towers, in one coach day out of Florence. These 15 differ on how long you get in each town, whether Pisa is bolted on and what the winery lunch costs.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Starting at Santa Maria Novella Station
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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

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

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Meet Walkabout Florence Tours at Santa Maria Novella Station for a full day through Tuscany. Guides such as Alex, Sara, Davide, and Manolo lead the group to Siena, San Gimignano, Pisa, and a Chianti winery lunch with four wine tastings. Expect plenty of walking, free time, and a maximum group size of 40.

“We went on this day trip during our honeymoon in October 2025. This excursion was an outstanding experience thanks to our tour guide, Giancarlo. He was engaging, informative, funny, and knowledgeable. Siena, San Gimignano, Pisa, and lunch at the winery were beautiful. It is a long day so be sure to dress comfortably. This day trip was one of the highlights of our trip. We highly recommend going on this tour.”

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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch - Getting out of Florence and onto the road
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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch

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

★★★★★★★★★★4.6 · 9,771 reviews · 12 - 12.5 hours · from $58

Travel from Florence by coach to Siena, San Gimignano, Pisa, and a Chianti winery. Choose a basic or full option, with Tuscan lunch, wine tasting, an English guided tour of Siena, and cathedral entry available. Guides such as Val, Luca, and Leonardo add history and practical help along the way.

“Excellent day trip guided tour! Well planned, organized, explained, and executed. I highly recommend this tour!!!”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting in Florence and settling into the coach
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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

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

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52

Travel from Florence to Pisa, San Gimignano, Siena, and the Chianti Hills in 12 hours. You get free time in each town, with optional Leaning Tower tickets, a Siena walking tour, and a winery lunch with tasting. Guides such as Barbara and Anna add useful local tips along the way.

“Our guide Hillary was very knowledgable and provided excellent explanations of the places that we visited including their history and some curiosities as well as some recommendations of places to visit and traditional food to taste. The tour was very well organised and allow us to have a good insight into the region. Our bus driver Salvatore was also really nice and we appreciate his contribution to the success of the tour. I would recommend this tour to anyone visiting Firenze.”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena Cathedral is worth a ticket if time allows
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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

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

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

From Florence, visit Siena, San Gimignano, and Pisa by air-conditioned coach. Choose guided Siena touring and a three-course winery lunch with wine pairing. Expect a long, well-paced day with plenty of walking, free time, and guides such as Jacopo, Sara, or Constantine depending on departure.

“What a great day! Sienna cathedral is stunning - a must visit. The wine pairing was very entertaining and good fun and the meal was tasty. San Gimignano was beautiful and I would really recommend going up the tower for some stunning views. The leaning tower of Pisa speaks for itself. The organisation of a big group was well managed and the tour guides were exceptional, keeping everyone updated in English and Spanish. All in all a great day.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Meeting the coach at Santa Maria Novella
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

5.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Travel from Florence by comfortable coach to Siena, San Gimignano, Pisa, and the Chianti Hills. Expect a guided Siena walk, Siena Cathedral entry, free time in three towns, and an optional winery lunch with four regional wines. Guides such as Alessandro, Sara, and Alex are known for lively storytelling.

“Wonderful, enriching day trip. Lunch was delightful, more than expected, with a gorgeous view. Our guide, Davido, was enthusiastic, knowledgeable, attentive and fun! It was amazing to be at Pisa for sunset, as the light was perfect. I wouldn’t change a thing. It would be hard, however, for folks with accessibility issues as there is a lot of walking and hills to deal with.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and its forest of towers
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Leave Florence by coach for San Gimignano’s towers, Monteriggioni’s medieval walls, a Chianti winery lunch with three wines, and Siena’s cathedral and Campo. Choose between free exploration and added Siena guiding. Expect hills, uneven streets, and a full 11-hour day.

“We have been to Italy many times and have been on dozens of tours. This tour was - by far - the worst tour ever. There were 75-80 people on our tour. Who would ever sign up for a tour, anywhere, with that many people? We were loaded onto a double decker bus and the tour company paired our English speaking tour with a Spanish speaking tour. Every discussion/announcement was in 2 languages. Moving that many people from one location to the next was an effort and took away from the time that could have been spent in any of the location stops. One of the worst parts of the…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Starting at Piazzale Montelungo
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

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

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

This 12-hour coach tour links Pisa, San Gimignano, Chianti, and Siena from Florence. Expect a busy but well-planned day, English or Spanish guidance, Siena touring options, and a three-course Tuscan lunch with three wines and Vin Santo if selected.

“We had an excellent trip, thanks to our fabulous guides. The bus was easy to access, and the time spent at each location was perfectly spaced.”

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Florence: Siena, San Gimignano & Monteriggioni with Tasting - Monteriggioni: a small village with a big wall
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Florence: Siena, San Gimignano & Monteriggioni with Tasting

8.Siena, San Gimignano & Monteriggioni with Tasting

★★★★★★★★★★4.6 · 3,218 reviews · 11 hours · from $46Best value

Spend 11 hours exploring Tuscany by air-conditioned coach, with stops in Monteriggioni, Siena, and San Gimignano, plus three Chianti wines and local snacks. Choose the guided Siena option for added context, or keep more time to yourself with the semi-independent version.

“Liked that the guide could speak fluent English and was knowledgeable about the tourist areas/history and explained well. He also gave clear instructions on the start /stop times reassembling locations etc. your was very well organized.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - A short hour in San Gimignano
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Spend about 10.5 hours exploring three Tuscan towns from Florence by air-conditioned coach. See Siena’s Piazza del Campo and Duomo, wander San Gimignano, stop at Monteriggioni, and taste two or three Chianti wines with regional snacks. Choose guided Siena sightseeing or more free time.

“Ronaldo and Roberto did a great job of getting us to our destinations and communicating things to do at each stop. This tour is a large group tour on a coach bus. We still kept to our schedule. Siena is beautiful along with the other stops. The only thing i wish were different was the order of the stops. It was close to dark when we arrived to San Gimignano and would have preferred to be in Siena in the evening. Thanks for conducting the tour, so we could see more on our Italy trip!”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano and its famous towers
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

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

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You get free time in the hill towns, a three-course lunch, three-wine tasting, and optional Siena Cathedral access. Guides such as Aaron, Marta, and Ricardo have led recent departures.

“We had ample time in each location, as well as recommendations from the guide on what to do. The wine tasting & lunch were fantastic, would highly highly recommend, both delicious and engaging! Illaria was an excellent guide!”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Siena and the Piazza del Campo
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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

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

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78

Leave Florence at 7:30 am for a full-day bus tour through Tuscany. Walk Siena with a local guide, visit its cathedral if selected, eat at a family-run winery, explore San Gimignano, and see Pisa’s famous square and Leaning Tower. English service, with some departures combining languages.

“Whilst this is a long day, it was worth it to see all the sights we saw! Our favourite stop was Siena, we would have loved to spend more time there. Lunch at Sam Gimignano was really nice. Our guide at Siena was quite difficult to understand and very breathy, she was struggling with the inclines. It was good to understand the history but also lovely to walk around on our own.”

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Siena and San Gimignano: Small-Group Tour with Lunch from Florence - Siena and the open curve of Piazza del Campo
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Siena and San Gimignano: Small-Group Tour with Lunch from Florence

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

★★★★★★★★★★5.0 · 1,675 reviews · 10 hours (approx.) · from $180

Leave Florence at 8 a.m. for Siena, Monteriggioni, a family-run winery, and San Gimignano. Expect guided sightseeing, a seasonal Tuscan lunch with wine, and free time in both hill towns. Guides such as Lorenzo, Susie, and Leonardo are known for lively storytelling, while the group can reach 25 people.

“Very nice experience. Lorenzo and Alex were great. Lunch at winery was very good and very pretty. Very prompt, professional, courteou, informative and friendly.”

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Florence: Day Trip with Free Time in San Gimignano and Siena - The ride through Chianti to San Gimignano
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Florence: Day Trip with Free Time in San Gimignano and Siena

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

★★★★★★★★★★4.7 · 1,624 reviews · 9 hours · from $71

Travel by air-conditioned bus from Florence to San Gimignano and Siena, with about two and a half hours in each town. Your tour leader, such as Sara, Sarah, or Alessandra, provides an orientation, maps, suggestions, and audio-guide help, leaving you free to explore.

“We thoroughly enjoyed our trip. It was very well organised. The guide was friendly and informative with good recommendations and the driver was also friendly and funny. We would recommend.”

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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch - San Gimignano is the prettiest pause
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Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

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

★★★★★★★★★★4.5 · 1,108 reviews · 12 hours 15 minutes (approx.) · from $59

Start in Florence and spend 12 hours visiting Pisa, San Gimignano, a Chianti winery, and Siena. You’ll have free time in Pisa and San Gimignano, a Tuscan lunch with wine, and an English guided walk in Siena. Guides such as Marco, Niccolò, and Luca are noted for clear, friendly storytelling.

“This was a wonderful excursion but be prepared to walk a lot. It was actually more than I anticipated. We did however get to see some beautiful sights.”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence - Meeting at Porta Romana at 9:45am
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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

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

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229

Leave Florence at 10am for two winery visits in the Chianti and Vernaccia regions. Taste eight wines with Tuscan foods, then explore San Gimignano for 90 minutes. Guides such as Emanuele, Valentina, Giovanni, and Ned add local history and practical help.

“Ottavio guided a perfect day in Tuscany as we visited two wineries and the walled town of San Gimignano. On the drive from Florence, Ottavio kept us entertained with both personal stories of growing up in Tuscany and the history of the region. We could NOT have asked for a better experience or guide.”

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