Florence

15 Best Tuscany Day Trips from Florence

The Tuscany day trips Florence travelers book most: Siena’s shell-shaped piazza, San Gimignano’s towers and a winery lunch stitched into one loop.

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

Explore Tuscany in a single day with visits to Siena, San Gimignano, Pisa, and a vineyard lunch—guided, scenic, and full of authentic Italian charm.

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

Discover Tuscany’s highlights on a full-day trip from Florence, including Pisa, Siena, San Gimignano, and wine tasting — a perfect mix of history, scenery, and flavor.

★ 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.”

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

Explore Tuscany on a full-day trip from Florence, visiting Siena, San Gimignano, and Pisa, with optional lunch, wine tasting, and free time in charming towns.

★ 4.5

““Such a wonderful experience! Everything was perfectly organized, the guide was very kind and professional. The places we visited were beautiful and truly worth seeing. I highly recommend this excursion!””

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4.Wine Safaris: Off Road Tuscany Wine Tours and Lunch from Florence

Experience Tuscany’s best with off-road wine safaris from Florence, visiting historic vineyards, tasting top wines, and savoring authentic Tuscan cuisine.

★ 5.0

“Genie was such a wonderful tour guide- so sweet and knowledgeable!! My partner and I loved the wine from the first and third wineries the best and the second winery had such beautiful views! Our driver Christoph was also great at getting us to the…”

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

Discover Tuscany in a day with visits to San Gimignano, Siena, Monteriggioni, plus wine tasting and a delicious local lunch. Perfect for history lovers and wine enthusiasts.

★ 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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6.From Florence: Siena, San Gimignano & Monteriggioni Tour

Discover Tuscany’s highlights with this full-day tour from Florence, exploring Siena, San Gimignano, Monteriggioni, plus wine tasting in Chianti.

★ 4.6

“Alex our guide was friendly, knowledgeable and engaging. Massimo the bus driver was friendly and happy too. We had a wonderful day exploring the beautiful enchanting towns in the Tuscany countryside. The winery was very generous with their wine portions, very interesting information about the…”

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

Explore Tuscany's medieval highlights—Siena, San Gimignano, Monteriggioni—with wine tasting, guided tours, and free time, all from Florence for $64.

★ 4.5

“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…”

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

Explore Tuscany’s highlights in one day with visits to Pisa, Siena, San Gimignano, and Chianti. Enjoy guided tours, a traditional lunch, and wine tasting for a memorable experience.

★ 5.0

“A very worthwhile trip. Long day but packed full of things to do and see. Our tour guide Sandro was amazing.”

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

Discover the charm of Tuscany on this small-group guided tour from Florence to Siena and San Gimignano, including a wine lunch and free time to explore.

★ 5.0

“Although I am happy to give this tour an outstanding reading unfortunately this is the fourth time I have tried to provide you with details. On each other occasion, the information I provided has vanished and your system does not maintain what was previously written.…”

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

Discover Tuscany’s charm with this full-day trip from Florence to San Gimignano and Siena, featuring free time, stunning views, and expert guides for an authentic experience.

★ 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…”

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11.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

Discover Tuscany’s scenic Chianti hills on a guided bike tour, featuring wine tasting, olive oil sampling, and a delicious Tuscan lunch—perfect for active lovers of authentic flavors.

★ 5.0

“I highly recommend this tour especially if you want to get out of Florence and explore the countryside without going too far away. I am a solo traveler and I felt comfortable. If you’re like me and need to know all the details before you…”

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

Experience Tuscany's highlights on this full-day Florence tour visiting Pisa, San Gimignano, Siena, with wine tasting and authentic Tuscan lunch.

★ 4.5

“It was an unforgettable experience, where we were able to visit three beautiful towns with a rich history. Both the tour and the guide are highly recommended.”

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13.Tuscany Wine tour & San Gimignano from Florence

Discover the beauty of Tuscany with this full-day wine tour from Florence, featuring visits to authentic wineries, San Gimignano exploration, and tastings of world-famous wines and regional products.

★ 5.0

“Fantastic wine tasting tour! Both locations offered a good selection of wine and food. Visiting San Gimignano was a cool addition. Valentina was a great guide!”

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15.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

Discover Tuscany’s best with this full-day Chianti winery tour from Florence, including guided visits, tastings, a Tuscan lunch, and San Gimignano.

★ 5.0

“My wife and I did the small group tour to Tuscany and San Gimano and had the best time. We would highly recommend this anyone wanted a fun experience with good company.”

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More Tuscany Day Trips from Florence

5.0E-Bike Florence Tuscany Self-Guided Ride with Vineyard Visit4 to 7 hours (approx.)$96.74 4.5San Gimignano, Siena and Chianti Small Group Wine Tour11 hours 30 minutes (approx.)$167.74 4.5Tuscany Experience: Pisa, Siena, San Gimignano & 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 Tour: Lunch & Wine Tasting, Countryside Roads5 hours (approx.)$228.62 5.0Tuscany Vespa Tours Through the Hills of Chianti6 hours (approx.)$193.49 5.0Tuscany Vespa Tour from Florence with Wine Tasting7 to 8 hours (approx.)$241.86 5.0Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence8 hours (approx.)$834.79 4.0Afternoon in Siena and Chianti Wine Tour with Dinner from Florence7 hours 30 minutes (approx.)$106.65 5.0Florence to Tuscany: Chianti, Siena, San Gimignano & Wine + Lunch9 hours (approx.)$235.92 5.0PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence8 to 9 hours (approx.)$399.25 5.0Experience the Magic of Tuscany from a Hot Air Balloon3 hours (approx.)$325.45 4.5Tuscany E-Bike Tour: from Florence to Chianti with lunch and tastings$138.17 5.0Tuscany Half day biking with oil producer, Chianti wine and food4 hours (approx.)$95.58 5.0Hot Air Balloon flight in Tuscany countryside from Chianti3 hours (approx.)$325.45 4.5Florence: Siena & San Gimignano with Dinner in a Boutique Winery9 to 12 hours (approx.)$126.30 5.0Wine Tasting Experience in Ponte Vecchio: Best Tuscany selection!1 hour (approx.)$36.30 5.0Semi Private Deep Wine Chianti and San Gimignano from Florence8 hours 30 minutes (approx.)$252.86 5.0Florence: Tuscany Grand Tour-Siena, San Gimignano, Chianti & Pisa8 to 12 hours (approx.)$169.45 5.0From San Gimignano: Tuscany Vespa Tour with Lunch & Wine Tasting6 hours (approx.)$180.27 4.7From Florence: Siena & San Gimignano Tour with Chianti Views9 hours$57 5.0Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence10 hours (approx.)$701.71 5.0Full-Day Small-Group Truffle Hunting in Tuscany with Lunch7 hours (approx.)$405.30 4.5Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region8 hours (approx.)$520.03