Florence · CHIANTI VINEYARD TRIPS FROM FLORENCE
31 experiences compared
A strong Chianti day balances the road, the cellars and the table. Compare Florence departures by estate count, tasting format, lunch, group size and return time, with the highest-evidence options first.
One full day covering Pisa, San Gimignano, Siena, and Chianti wine tastings, with guided Siena and optional Leaning Tower tickets.
“The guide Anna was super nice and very resourceful, she gave very interesting insights and explained everything clearly. Sights were amazing and then wine tasting experience was exceptional.”
Half-day Chianti Hills tour from Florence with two cantinas, guided vineyard walks, and tastings of 6 to 7 wines plus local foods.
“Great experience! Our guide Constantino and driver Ricardo were both fantastic. Both wineries were a good experience and had delicious wines”
Chianti day trip from Florence with San Gimignano, Monteriggioni, Siena, and a winery lunch plus wine tasting on an air-conditioned coach.
“This tour is a great way to see unesco towns with lots of history and charm in one day. It also included a light lunch which was only 2 courses not 3 as described and wine tasting which you can buy, if you don’t drink wine you get water.The guides Frederico Lillie and Fabbie were friendly and helpful. Overall an enjoyable day.”
12-hour Florence-to-Tuscany day trip to Pisa, San Gimignano, Siena and Chianti, with Siena guided walk and optional lunch.
“Amazing ! Sandro was so experienced and taught us so much about the culture.”
Chianti wine tasting tour from Florence with two organic wineries, scenic Via Chiantigiana views, and food pairings.
“Very nice wines and a small bit of food. 3 wines in each place, mainly red wine which is what the area is known for. Guides were very nice and knowledgable, would recommend”
Full-day Tuscany loop from Florence, with hilltop Monteriggioni, UNESCO Siena and San Gimignano, and a Chianti tasting with snacks.
“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 very good.”
Florence day trip to San Gimignano and Siena with a Chianti winery lunch and guided tasting. UNESCO sights, Cathedral option.
“We had the best trip! everything ran so smoothly, the guide was perfect thank you so much!”
Half-day Chianti tour from Florence with 2 wineries, 7 wine tastings, olive oil and balsamic, plus Monteriggioni free time.
“We had a great time. It was well organized and our tour guide was excellent. The bus was very comfortable, as well. The only thing I would add to help others in the future is to emphasize to take the local train to the meeting spot = which cost like 6E. We took an Uber costing us $60 😭 But nonetheless we had a great time at both wineries.”
A fast-paced Tuscany day trip from Florence to Pisa, Siena, San Gimignano and Chianti vineyards, with a winery lunch and 4-wine tasting.
“I signed up for English speaking but the tour was combined with Spanish speakers. I find people on the bus are rude (talking)while the tour guide speaks the other language. I think because the guide needs to speak in two languages, they cut short the information given. Also 50 people is too many for a tour that contains a lot of walking. Speaking of that, we spent about 20 minutes each way in each stop walking from to/from parking to tour beginning. That’s 2 hrs wasted! Tour guides need to speak slower while speaking in other languages.”
Half-day Chianti wine tour from Florence: two winery visits, vineyard walks, and tastings plus Tuscan bites on a Wi-Fi coach.
“Two very different wineries and experiences in one trip. Afternoon trip = beautiful sunset! Highly recommended.”
Ride a Vespa or Fiat Topolino from Florence into Chianti, stop for villages and wineries, and enjoy lunch with tastings.
“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…”
A guided Chianti bike ride from Florence with a medieval castle winery stop, wine and olive oil tasting, plus lunch in the countryside.
“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 assistance anytime it was needed. Each individual was exceptionally upbeat and pleasant to be with, so much so that we wanted to invite them to join us for drinks and dinner that evening! Unfortunately, we had another commitment that made that impossible … next time guys!! The tour was super informative, we learned a LOT, thank you Alessio! The winery tour was fascinating, and man…”
Small-group Chianti day trip from Florence: 3 winery visits, Tuscan lunch with tastings, and a Greve village stop for olive oil.
“It was such a good time! Jason and Sergio were amazing hosts. Beautiful countryside, great wine, good people!”
Half-day Chianti wine tour from Florence with two organic wineries, cellar walks, Chianti tastings, pecorino snacks, and scenic hill drive.
“It was lovely! Lots of great wine and informative speakers with breadth of knowledge. Cruisey drive as well!”
Private Chianti tour from Florence with Radda village time and two tastings. Visit wineries and sample olive oil and local foods.
“A wonderful afternoon, our guide Anna gave lots of information about our Tuscany wine tasting tour. Our coach driver did an amazing job driving around the hills and narrow roads.”
