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

“Loved seeing the old villages and Tuscany. The wine samples at the farm were delicious and the farm was beautiful. Would have loved even more time there. The views were incredible.”

Check Availability →Read our full review →

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!””

Check Availability →Read our full review →

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”

Check Availability →Read our full review →

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

“Too long too many directions. Too long in Siena. Restaurant was below average Felt like cattle being herded in”

Check Availability →Read our full review →

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

“I think the thing I enjoyed most was the ease of everything. It’s always nice to not have to worry about details and just focus on enjoying the moment.”

Check Availability →Read our full review →

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

“It was a good tour bit of a big tour but a very good tour.. You can miss the optional lunch which wasn't good at all and there are far better places to eat in Sienna. Also do take the optional Sienna tour which was…”

Check Availability →Read our full review →

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…”

Check Availability →Read our full review →

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

“Great day trip. Big comfy bus with a bathroom on board. Spent 3hr in each city which was perfect amount of time. Guide told us a couple facts and sent us a list of recommendations before each city. San Gimi is so picturesque - absolutely…”

Check Availability →Read our full review →

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

“Great day, Angus was very great and interesting. A beautiful day in small group make the day enjoyable.”

Check Availability →Read our full review →

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 tour was a fantastic way to explore the highlights of Tuscany. It was a long day, but absolutely worth it. The guides were excellent—friendly, organized, and very knowledgeable about the region. I highly recommend this experience to anyone wanting to get a well-rounded glimpse…”

Check Availability →Read our full review →

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

“Ema was a fantastic guide! I'd definitely recommend this tour for anyone looking to see the country side while staying in Florence. We saw lots but did not feel rushed, and were back in the city for dinner.”

Check Availability →Read our full review →

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!”

Check Availability →Read our full review →

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.”

Check Availability →Read our full review →

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