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 had a wonderful day visiting Siena, San Gimignano and Pisa. Excellent meal at the winery with plenty of food and wine. Our guide, Alessandro was excellent! Highly recommend the experience.”

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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

“Fabulous tour with guide Simone and Roberto. This was the best part of our trip. Thankful to see Pisa, Siena and San Gemignano was spectacular and the wine tasting with luncheon was very memorable.”

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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

“Gloria and Roberto were amazing guides. Not only were the wineries diverse, but the knowledge shared was informative and interesting. Gloria also took the time to answer questions and ‘get to know the group’. Roberto was a smooth and careful driver.”

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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

“Lovely informative day to see a slice of Tuscany. Our guides were great and the bus very comfortable. Met some lovely people also. Would recommend this tour.”

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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

“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…”

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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

“Great tour guide (Susie) and comfortable bus. Stopped between visiting the towns at a small farm and got to learn about olive oil production and had a great lunch. We were lucky to have shared the experience with some great people (TOTAL BONUS).”

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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

“even with Rain was a wonderful trip, Sarah was really nice and maybe just a little bit more time in Siena would be 10/10 but we really enjoyed 😉”

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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

“This was the BEST tour by far! The guides, Ben & Angus were friendly, personable, & knowledgeable. The bike ride was awesome and the wine spectacular. This is a must if you want out of the city to explore Tuscany and be active.”

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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

“Great Tuscan Wine tour! Luigi was our guide, he was knowledgeable and entertaining. One of best tours.”

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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

“This tour was excellent. Really enjoyed all the sights. Especially Siena and of course the iconic Pisa. If you’re short on time, highly recommend it!”

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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

“Amazing. Worth every penny!!! a driver was wonderful. The food and wine was amazing. It was absolutely wonderful. It was a great combination of food, wine, and being able to visit the town with the cherry on top.”

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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