Florence

15 Best Tuscany Day Trips from Florence

Day trips out of Florence, sized up: Siena, San Gimignano, Pisa and the Chianti hills in various combinations. The classic four-stop day runs about twelve hours, which is a lot of van. Lunch inclusions vary wildly, so read the fine print before you pick.

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

Step into the past with a Tuscany day trip from Florence, exploring Siena, San Gimignano, Pisa, and more—unveiling Italy's hidden gems and culinary treasures.

Most Popular★ 5.0

“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…”

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2.From Florence: Day Trip Pisa, Siena & San Gimignano W/Lunch

Discover the wonders of Tuscany in just one day! Explore Pisa, Siena, and San Gimignano with a delicious lunch included. Don't miss out, click now!

★ 4.6

“It was a long day, but worth it. it was very well organised, nice lunch, enough time at each stop. The tour operators gave us a great history background of each destination. I would definitely recommend this tour.”

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3.Florence: Pisa, Siena and San Gimignano Day Trip With Lunch

Get ready to uncover the hidden gems of Tuscany on a day trip from Florence to Pisa, Siena, and San Gimignano, where surprises await.

★ 4.6

“Our guide was excellent. Luca made sure to connect with everyone. I was interested in the art but also the history. Luca, was available to answer questions as we walked to the site. i would request him.”

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6.From Florence: Tuscany Day Trip With Lunch at Chianti Winery

Discover the enchanting beauty of Tuscany in a day trip from Florence. Indulge in a mouthwatering lunch at a Chianti winery. Click now for an unforgettable adventure!

★ 4.8

“Without a doubt, it was a great tour. We loved it so much! Alessandro was enthusiastic, charismatic, and much more. He goes above and beyond to deliver us a good time. And Ali on the steering wheel, wow, if he had a nickname, he should…”

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7.San Gimignano, Siena, Monteriggioni, Chianti Day Trip With Lunch & Wine Tasting

Embark on an unforgettable journey through the enchanting landscapes of San Gimignano, Siena, Monteriggioni, and Chianti. Immerse yourself in authentic Italian culture with a delightful lunch and wine tasting. Click now!

★ 4.5

“We had a day trip to San Gimignano and Siena. The tour was amazing and well-managed. All thanks to Alessandra and Enrico. The lunch and wine tasting experience were good. The guided visit to Siena was merged with another language, thus, making it difficult to…”

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9.From Florence: Small Group Wine Tasting Tour to Tuscany

Experience the exquisite flavors of Tuscany on our small group wine tasting tour from Florence. Uncover hidden gems and indulge in the rich heritage of Italian winemaking.

★ 4.9

“The tour was fantastic. Jason our guide and Alessio our driver made the whole experience so fun. The two vineyards we visited were beautiful, the guides knowledgeable and the wine was fantastic. It was a good sized group, well-organized and perfect for a four hour…”

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10.From Florence: San Gimignano, Siena, and Monteriggioni Tour

Discover the charm of medieval Italy on our San Gimignano, Siena, and Monteriggioni Tour. Immerse yourself in history, culture, and breathtaking landscapes. Book your adventure now!

★ 4.5

“Marco was a fantastic guide with relevant and interesting information, while also leaving a good amount of free time to explore by yourself. When we boarded the bus we were offered an optional lunch at the Winery for an additional fee (€20) which most people…”

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11.From Florence: Siena, San Gimignano & Monteriggioni Tour

Discover the enchanting beauty of Siena, San Gimignano & Monteriggioni on this unforgettable tour from Florence. Experience the magic of Tuscany and book your adventure now!

★ 4.6

“Thank you to Pat & Gabriele for a great tour of Tuscany including Siena and San Gimangiano, was an informative & entertaining ride to each town. Recommend for a great day trip, and the inclusion of the wine tasting was fabulous even for a non…”

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12.Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Discover the enchanting medieval wonders of Tuscany: Siena, San Gimignano, and Monteriggioni. Uncover hidden gems and immerse yourself in history. Click now for an unforgettable journey!

★ 4.5

“The venues are great. The organisation from Gabrielle was spot on he is funny and numerous even when pouring with rain. Felt confident with Ferdi’s driving on narrow roads with a big bus! Great day out.”

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

Discover the enchanting beauty of Florence and indulge in the flavors of Chianti with a wine tasting lunch. Uncover hidden gems in S. Gimignano and Siena.

★ 4.6

“The trip was great! San Gimignano and Siena were both beautiful. Our guide was kind and knowledgeable. The bus ride was SMOOTH and we had plenty of free time the whole day. Plus I had the best gelato I’ve ever tasted in Siena once again!…”

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

Immerse yourself in the enchanting landscapes of Tuscany, where each town holds a secret worth discovering - are you ready to unlock their mysteries?

★ 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…”

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15.From Florence: Tuscany Wine & Food Tour With Guide

Discover the exquisite flavors of Tuscany on our guided wine & food tour. Indulge in the rich history and taste the essence of Italy. Book now!

★ 4.9

“This was an awesome day! Our guide Jonathan was fantastic. He had a lot of knowledge and also kept the day fun! Our driver Antonio was also awesome :) Overall, I recommend this tour. I will say the wine tasting is about 80% red wines…”

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5.0Siena and San Gimignano: Small-Group Tour With Lunch From Florence10 hours (approx.)$180.19 4.7Florence: Day Trip With Free Time in San Gimignano and Siena9 hours$71 5.0Small-Group Tuscany By Vespa6 hours 30 minutes (approx.)$125.28 5.0Tuscany Bike Tours: One Day Bike Tour Through the Hills of Chianti6 hours (approx.)$145.12 4.5Florence Day Trip: Pisa, San Gimignano, and Siena With Lunch12 hours 15 minutes (approx.)$59.13 4.5Tuscany Hills Postcard View:Val Dorcia Scenery With Wine Tasting11 hours 30 minutes (approx.)$94.57 5.0Tuscany Wine Tour7 hours (approx.)$229.77 4.6From Florence: Tuscany Highlights Full-Day Tour11.5 - 12 hours$46 5.0E-Bike Florence Tuscany Ride With Vineyard Visit4 to 7 hours (approx.)$96.74 4.5Full Day: Wine Experience in San Gimignano, Siena & Monteriggioni11 hours 30 minutes (approx.)$167.74 4.5Tuscany Experience From Florence:Pisa,Siena,San Gimignano & Chianti Wine Tasting11 hours 30 minutes (approx.)$53.33 4.5From Florence: Small-Group Tuscany Wine & Oil Tour With Typical Tuscan Meal7 hours (approx.)$96.86 5.0Tuscany Vespa Tour5 hours (approx.)$228.62 5.0Tuscany Vespa Tours: One Day Vespa Tour Through the Hills of Chianti6 hours (approx.)$193.49 4.8From Florence: Tuscany Wine Tour Full-Day Trip$84.96 4.7Tuscany by Vespa Full-Day Tour to Chianti Wine Region$135.04 4.6Florence: Tuscany Day Trip to Siena & San Gimignano$58 4.9Florence: Siena, San Gimignano and Chianti Small Group Tour9 hours$175 4.6Florence: Siena & San Gimignano Day Trip With Lunch & Wine$84.96 5.0Tuscany Vespa Wine Tour From Florence7 to 8 hours (approx.)$241.86 5.0Private Tour in Siena, San Gimignano and Chianti Day Trip From Florence8 hours (approx.)$834.79 4.3From Florence: Tuscany Hills Wine Tour$146.14 4.0Afternoon in Siena and Chianti Wine Tour With Dinner From Florence7 hours 30 minutes (approx.)$106.65 4.9Florence: Balloon Flight Over Tuscany$305.87