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

“Manolo and his team took great care of us and were so knowledgeable about all the places we went to. The sights were fabulous and the winery was absolutely exceptional! We had plenty of free time to explore, buy some souvenirs and make life long…”

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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

“We absolutely loved this trip! It was the best. It was a pretty big day and by the end of it youre definitely tired but its awesome. We were able to see so many places, whilst having an opportunity to rest in between each 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

“Guide was informative and fun. The wines were good as was the food served. The grounds and estate were lovely. Met lovely people from across the world and had great conversations. Only adults on this tour but they were of all ages. Highly recommend”

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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

“Beautiful lunch and towns visited, luxury coach and quality guide Constantino and Alessia / Alexa and driver Claudio was fab”

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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

“Sara and Lorenza were great tour guides. Mario a safe bus driver. Bus was comfortable. Knowledgeable professional and most pleasant”

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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

“It was a great trip, I’m a vegetarian and the food was great. We brought our daughter who was 14 months and the tour was great for her.”

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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

“An outstanding tour experience. The guide was extremely kind, professional, and highly knowledgeable, providing clear and engaging explanations throughout. The timing at each location was perfectly planned, allowing us to fully enjoy every stop without feeling rushed. The driver was very skilled and made 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

“Do not hesitate for one single second to book this tour! We had such a wonderful family experience with the kind assistance of all involved. There were three tour guides (Allesio, Filippo, and Ben), and Lorenzo, the travel assistant who shadowed our ride to provide…”

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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

“This is an extremely interesting, fun, great and well organised tour ❤️ The guides Alessia (Italian) Giulia (Portuguese) and Fabrizio (Spanish) were EXCELLENT, very polite, informative and patient. They explained in detail what we were about to see and do, and took care of everyone…”

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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 experience in both wineries and San Gimignano! Our guide Giovanni was amazing! Thank you Giovanni!”

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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

“There was a horrible couple from Australia/New Zealand who kept changing seats and disturbed passengers altering the seats of everyone else. They were rude to everyone including the guide. The guide was patient and very nice. Just want to write this just in case they…”

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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