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

“I had a fantastic experience with this tour guide Sara and Milano from start to finish. Everything was well-organized, smooth, and thoughtfully planned, which made the entire tour stress-free and enjoyable. Sara was knowledgeable, engaging, and passionate, sharing interesting facts and stories that really brought…”

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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

“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.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

“Well organised, clear instructions given. Important to keep to scheduled times allocated to each stop. Think reasonable time allocated for each stop, including if want to enter Siena Cathedral, lunch etc. But got to be realistic with use of time, 2 cities and a town…”

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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

“Do wait, sign up and do it! what a fantastic experience!! Going through the country side, and seeing the vineyards, the lunch and knowledge was just great!!”

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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

“Guide Alejandra was knowledgeable and give us the information in English and Spanish. The three medieval towns were charming and worth visiting as well as the family owned winery and olive oil producers. The Tuscan meal was simple (typical) and good. The family vineyard owners…”

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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

“We had a brilliant day with Martina, Constantin and Mario! Everything went smoothy and we experienced Tuscany in a lovely way. Highlight was the wine tasting and San Gimignano! Thanks to Ciao Florence for amazing experience!”

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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

“So we'll planned. No details are left to chance. They do such a good job of informing you of starting points, scheduling meetups etc. Our host Alex was wonderful and very knowledgeable. Seemed as though he was enjoying himself as much as we were. My…”

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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

“I signed up for English speaking but the tour was combined with Spanish speakers. I find people on the bus are rude (talking)while the tour guide speaks the other language. I think because the guide needs to speak in two languages, they cut short the…”

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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

“Tour was fun and informative. The driver and guide were amazing. In my opinion the food at lunch was OK. After many good meals in Florence it was somewhat disappointing.”

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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

“Perfect! I enjoyed both cities! Sara gave us amazing recommendations for everything - places, museums, churches, wines!”

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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

“Super fun - the right mix of physical activity (20k ride), sights, info and culture. Relaxed vibe, bright and friendly guides with excellent English. Beware the final hill at the end, if you aren’t a fit avid cyclist take the vehicle transport option ;) but…”

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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

“Giovanni was an amazing tour guide! He was so knowledgeable and so much fun. He made everyone feel so welcomed. It was truly such a great tour and a great day of experiences. The wine was amazing in both locations. Thank you!!”

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14.From Florence: Tuscany Highlights Full-Day Tour

Discover Tuscany's highlights in one day with visits to Siena, San Gimignano, Pisa, and the Chianti countryside, including lunch and wine tasting for a balanced, authentic experience.

★ 4.6

“All the details of the trip were amazing. Gabrielle and Fede did a fantastic job enjoying we knew what to do and where to be. Would have loved more time in San Gimignano. Enjoyed all the details from the comfort of the transportation to lunch…”

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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