The 15 Best Tuscan Vineyard Tours

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

/ August 8, 2026

1.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Our pick

Full-day Tuscany highlights from Florence: Pisa, San Gimignano, Siena, and Chianti wine tasting, with optional Leaning Tower tickets.

“Good value for money, hassle-free and transportation was comfortable. Didn't feel rushed and timing of destinations were perfect as other tour buses evenfually came after so places weren't too crowded when we arrived.”

Check availability →Read our full review

Florence Tours, Food & Drink, Tour Reviews, Tours, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Florence: Chianti Wineries Tour with Wine Tasting

/ August 8, 2026

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56.37

Half-day Chianti tour from Florence with two cantinas, vineyard walks, and wine tastings plus Tuscan snacks in the hills.

“The tour was fantastic! Our guide Gulia was very knowledgeable about wine, and the region. She made everyone feel welcomed! The wine tastings and vineyards were great! An amazing experience!”

Check availability →Read our full review

1-Day Tours, Food & Drink, Lunch Experiences, Rome Tours, Tour Reviews, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Rome

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

/ August 8, 2026

3.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83.44

12-hour Tuscany day trip from Rome with Montepulciano, Tempio di San Biagio, Pienza, plus farm lunch and wine tasting.

“This was a long day but it was worth the hours on the bus. Montepulciano was a beautiful city and the views were priceless. Our guide was very entertaining.”

Check availability →Read our full review

1-Day Tours, Day Trips from Florence, Florence Tours, Food & Drink, Lunch Experiences, Tour Reviews, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

/ August 8, 2026

4.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83.27

San Gimignano towers, Monteriggioni walls, Chianti lunch and 3-wine tasting, then Siena cathedral and plazas on a Florence day trip.

“This tour was well worth it. We enjoyed discovering the medieval towns inTuscany, lunch was tasty, bus was comfortable. The three staff assigned to our tour were Alexandra, Stella & Nino and they were all lovely & wonderful! Highly recommended tour!”

Check availability →Read our full review

Florence Tours, Lunch Experiences, Tour Reviews, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

/ August 8, 2026

5.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

12-hour Tuscan day trip from Florence with Pisa, Siena, San Gimignano, Chianti countryside, plus optional lunch and wine pairing.

“Our guide, Aaron and Fabi, were excellent guides! Ferdinand was an amazing driver! I highly recommend this tour!”

Check availability →Read our full review

Florence Tours, Tour Reviews, Tours, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Chianti Wine Tour from Florence

/ August 8, 2026

6.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59.13

Chianti wine tour from Florence with two organic wineries, guided tastings and local food, plus a scenic Via Chiantigiana coach ride.

“Both wineries were amazing! Lots of Knowledge about making the wine and very personal wanted you to ask questions and just talked to you during the tour. Tommas from the second location super friendly and did an excellent job! Both shipped to the US and you could buy another glass while you walked around the site. Both had some snacks at the venues, but would eat lunch or dinner before going.”

Check availability →Read our full review

Siena Tours, Tour Reviews, Tours, Tuscan Vineyard Tours, Wine Tours

From Florence: San Gimignano, Siena, and Chianti Wine Tour

/ August 8, 2026

7.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164.26

Florence to Tuscany in one day, with Siena sights, a Chianti estate five-wine tasting, and San Gimignano towers plus a truffle lunch.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.”

Check availability →Read our full review

Florence Tours, Tour Reviews, Tours, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ August 8, 2026

8.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78.60

Hit Siena, San Gimignano, and Chianti from Florence in one long, well-guided day with medieval stops and a fun wine tasting.

“Nice Tuscany day tour. Alex was great in explaining about the various areas we visited, and the driver Cozimo did a good job getting us back safe.”

Check availability →Read our full review

Florence Tours, Food & Drink, Lunch Experiences, Tour Reviews, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

/ August 8, 2026

9.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89.50

A smooth Florence day trip to San Gimignano, Siena, and Chianti with a winery lunch and tasting, plus optional Siena Cathedral entry.

“Absolutely loved San Gimignano… by far the favorite party of this trip. If I was to do it over I would skip the winery and stay here for more time. sienna was lovely as well. The wine tasting and lunch was average but the small towns were definitely the highlight. Aaron and Alexandra were great hosts and very knowledgeable!”

Check availability →Read our full review

Florence Tours, Half-Day, Tour Reviews, Tours, Tuscan Vineyard Tours

From Florence: Chianti Half-Day Afternoon Tour

/ August 8, 2026

10.Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55.80

Half-day Chianti wine tour from Florence with two cellar visits, tastings, olive oil and balsamic sampling, plus free time in Monteriggioni.

“Very well planned and arranged trip! Marta is an amazing fun guide :) you get enough info & time at every location. great experience”

Check availability →Read our full review

1-Day Tours, Day Trips from Florence, Florence Tours, Tour Reviews, Tuscan Vineyard Tours

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

/ August 8, 2026

11.Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78.60Top rated

One day Tuscan highlights from Florence: Pisa, Siena, San Gimignano and Chianti, plus a winery lunch with 4-wine tasting.

“Whilst this is a long day, it was worth it to see all the sights we saw! Our favourite stop was Siena, we would have loved to spend more time there. Lunch at Sam Gimignano was really nice. Our guide at Siena was quite difficult to understand and very breathy, she was struggling with the inclines. It was good to understand the history but also lovely to walk around on our own.”

Check availability →Read our full review

Florence Tours, Half-Day, Tour Reviews, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Half day Chianti Vineyard Escape from Florence with Wine Tastings

/ August 8, 2026

12.Half day Chianti Vineyard Escape from Florence with Wine Tastings

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53.10

Half-day Chianti vineyard escape from Florence with two winery visits, cellar walks, and up to 3 to 4 tastings per stop.

“The wine tour was very fun and informative! A nice bus ride through Tuscany and an experience of two different wineries. Both places were very accommodating and the wine & additional tasty treats were very good. We had a nice sunny cool day in December and the scenery was beautiful!”

Check availability →Read our full review

Florence Tours, Lunch Experiences, Motorbike & Scooter Rentals, Scooter Rentals, Tour Reviews, Tours, Tuscan Vineyard Tours, Vespa Experiences

Chianti Vespa Tour with Lunch from Florence & E-car Option

/ August 8, 2026

13.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125.28

Ride a Vespa or electric Topolino through Chianti hills, stop in small villages, visit wineries for tastings, and enjoy a Tuscan lunch near Florence.

“This was a 10/10 experience! The guides were so informative and personable, which made the trip even better. The only guide we recall is Haider, but there was a female guide as well but we did not catch her name. You take a bus to a parking lot to get you out of the city and familiar with the vespas prior to taking them out on the road. We appreciated the professionalism from the guides as they will make sure anyone who is driving is competent with the vespas to ensure everyone is safe. Then, you hit the road and get to spend a good amount of time to drive…”

Check availability →Read our full review

Cycling Tours, Florence Tours, Food & Drink, Tour Reviews, Tours, Tuscan Vineyard Tours, Wine Tours, Wine Tours in Florence

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

/ August 9, 2026

14.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145.12

Cycle the Chianti hills from Florence, then taste wine and extra virgin olive oil at a medieval castle, with a Tuscan lunch.

“Angus was so friendly and knowledable. My family of 4 had a great time. The views were amazing, very worth the ride. There was a stretch at the end of the ride that was quite challenging so keep that in mind if taking young children.”

Check availability →Read our full review

Florence Tours, Lunch Experiences, Tour Reviews, Tours, Tuscan Vineyard Tours

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

/ August 9, 2026

15.Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

★★★★★★★★★★5.0 · 1,269 reviews · 8 hours (approx.) · from $180.19

Small-group Chianti tour from Florence with 3 wineries, Greve village stop, and a Tuscan lunch with tastings in 8 hours.

“Well, first and foremost, your guide Leonardo was fabulous and very entertaining in such a gentleman with a wealth of knowledge. Not once during the day do you feel rushed as we normally get to enjoy these delicious wines, but learn about not only the wines but the region around them as well. They executed the tour perfectly and professionally.”

Check availability →Read our full review