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

“What a wonderful Tour! Our tour guide Mirella was great! We were very blessed to have her! She had a lot of knowledge about everything! I definitely recommend this tour!”

Check Availability →Read our full review →

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

“Highly recommend it! Best experience in Italy, totally worth the time and money. Siena is beautiful, the wine experience is unique, San Gimognano and Pisa are a must see!”

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

“What a great day! Sienna cathedral is stunning - a must visit. The wine pairing was very entertaining and good fun and the meal was tasty. San Gimignano was beautiful and I would really recommend going up the tower for some stunning views. The leaning…”

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

“The tour was fantastic and exceed our expectations. Our guide/sommelier Genevra was excellent in every way. Her knowledge of the region and wine is almost as impressive as her warm personality. The vineyards we visited were stunning and the wine was excellent. Cannot recommend enough...you…”

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

“It feels very rushed in last portion of tour. We had a guide that walked entirely too fast and our chronic knee and back pain were exacerbated trying to keeep up. Guided tour wasn’t really necessary… save yourself the expense. Meal was delicious! We thoroughly…”

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

“Very beautiful countryside and stops. Bus driver Mario did an excellent job and Alex was very informative and did an excellent job as well. Thank you for a great tour!! Will recommend GYG to friends and relatives!”

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

“Got an overview from hosts on tour but be prepared to use limited time wisely. So much to see so little time. Group of 70 was managed well”

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

“This is probably my favorite excursion I’ve ever done anywhere in the world. The guides were amazing and the impeccable way it was planned enabled us to see an experience so much in a 12 hour. Period. Breathtaking views, amazing food, and a once in…”

Check Availability →Read our full review →

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

“Excellent tour. The local guide in Siena shared his love with the town. Our stop at a winery for lunch was also very informative. Keep in mind that this tour involves a lot of walking up and down hills with few spots to rest.”

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

“Sarah was a great leader and support person. It was good to have some suggestions for what to see. We loved climbing the arch near the Siena Duomo, and the tower in San G. Great suggestions and expectations. Could have used more time in San…”

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

“Fabulous tour riding through the vineyards and olive groves in the Chianti area. Picturesque and incredible scenery with stops to take photos. Finished with an educational & fun winery tour then lunch. Alessio was a fabulous guide, friendly, good humoured, knowledgeable and enthusiastic. At each…”

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

“The tour was amazing! The tour guides Marco, Raffi and Michelle were friendly, knowledgeable and helpful. They went out of their way to make sure everyone was enjoying themselves. They even went over and able their job to help us after my husband dislocated his…”

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

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

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

“Guide was fantastic. But Viator lied to me about what winery we were going to. Overpriced for the experience we had. Did not like that Viator sales people compete to get commission so they say anything to get the sale”

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