WINE TOURS · CHIANTI WINE TOURS

Chianti from Florence: 15 Wine Tours Compared

43 tours  ·  from $37 a head

Half an hour south of Florence the traffic stops and the sangiovese starts. The 15 below compare the two-estate afternoons against the full days that add Siena and San Gimignano, on price and on hours in the van.

Florence: Chianti Wineries Tour with Wine Tasting - First winery: a close look at small-scale wine making
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tastings in Italy, Wine Tours, Winery Tours, Winery Tours in Florence, Winery Tours in Italy

Florence: Chianti Wineries Tour with Wine Tasting

1.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Our pick

Travel from Florence to two Chianti wineries in about five hours. Meet local producers, walk through vineyards, taste up to seven wines, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Ana, Alex, John, and Martina add regional stories along the way. Morning departures offer the best light for vineyard views.

“The tour was amazing, we had a great time with Ana, she is great and kind. We visited two wineries, but the first one, La Lama, was amazing. You will not regret this experience.”

Check availability →Read our full review

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Chianti wine and the midday meal
1-Day Tours, Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Lunch Experiences, Tour Reviews, Wine Country Day Trips, Wine Country Day Trips in Florence, Wine Country Day Trips in Italy, Wine Tastings, Wine Tastings in Florence, Wine Tastings in Italy, Wine Tours

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

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

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Spend about 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, guided sights in Siena, and a winery lunch with three wines plus vin santo. Choose the Siena walking tour and cathedral option for added art and history. Guides may include Sandro, Marta, Alessandra, or Ilaria.

“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”

Check availability →Read our full review

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa and the Field of Miracles in 80 minutes
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Lunch Experiences, Tour Reviews, Wine Tours

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

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

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

Travel from Florence to Pisa, San Gimignano, Chianti, and Siena on a 12-hour guided day trip. You’ll see Pisa’s cathedral complex, walk San Gimignano’s medieval streets, enjoy an optional Tuscan lunch with three wines and Vin Santo, and explore Siena with a guide. English and Spanish tours are available.

“The day trip was great! It was a great value for the money especially with the included lunch. Frederico was a great tour guide!”

Check availability →Read our full review

Chianti Wine Tour from Florence - The Via Chiantigiana makes the ride worthwhile
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Tours, Wine Tours

Chianti Wine Tour from Florence

4.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach for two Chianti wineries along the Via Chiantigiana. Tour vineyards and cellars, taste six or seven Tuscan wines with local foods, and hear about winemaking from your guide and winery hosts. English and Spanish tours are available, with optional cooking class or lunch upgrades.

“The first winery was just okay but the second was really nice because of the property. The hosts were fun.”

Check availability →Read our full review

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena first: the medieval heart of the day
Chianti Wine Tours, Italy Wine Tours, Siena Wine Tours, Tour Reviews, Tours, Wine Tours

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

5.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Spend nine hours exploring Siena and San Gimignano, with a guided Chianti estate visit between them. You’ll taste five wines, sample olive oils and balsamic vinegar, and enjoy a Tuscan lunch. Guides such as Marco, Lyla, Marta, and Enrieta are praised for clear storytelling and keeping the day on time.

“We had a great day out. Lots if activity. We were kept very busy.”

Check availability →Read our full review

Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch - Lunch, wine, and the Chianti hills
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Lunch Experiences, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tastings in Italy, Wine Tours

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

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

★★★★★★★★★★4.6 · 3,102 reviews · 11 hours · from $82

Spend a full day beyond Florence with guides such as Ricardo, Marta, or Sandro, depending on the departure. Explore San Gimignano and Siena, visit Monteriggioni in season, and stop at a Chianti winery for a cellar visit, three-course Tuscan lunch, and tasting of three wines plus Vin Santo. Choose the Siena walking tour and cathedral visit for more guided context.

“Riccardo, Scirin and colleagues were fantastic hosts. Very knowledgeable and funny and full of interesting facts Also the organisation was superb in terms of pick up , ensuring we knew where to go and when to get picked up Nice meal and wine tasting was a bonus”

Check availability →Read our full review

From Florence: Chianti Half-Day Wine Tour with Tasting - First stop: Poggio ai Laghi and the opening tasting
Chianti Wine Tours, Florence Wine Tours, Half-Day, Italy Wine Tours, Tour Reviews, Tours, Wine Tours

From Florence: Chianti Half-Day Wine Tour with Tasting

7.Chianti Half-Day Wine Tour with Tasting

★★★★★★★★★★4.5 · 3,031 reviews · 6 hours · from $58

Leave Florence by tram and coach for two Chianti wineries, where you taste seven wines with olive oil, balsamic vinegar, salami, cheese, and bruschetta. Guides such as Luca, Luciano, Marco, Tula, Alicia, and Leonardo have led recent departures. You also get 40 minutes in medieval Monteriggioni.

“We loved our trip! Could've done with about 20 mins longer in each winery, but the guides at each one were exceptional, and so knowledgable! Thank you so much :)”

Check availability →Read our full review

Siena, San Gimignano and Chianti Wines Day Tour from Florence - Starting at Piazzale Montelungo in Florence
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Tours, Wine Country Day Trips, Wine Country Day Trips in Florence, Wine Country Day Trips in Italy, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Travel by air-conditioned coach from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate. You’ll get guided time in Siena, free time in the hill towns, and a tasting of two or three wines with local snacks. Guides such as Alex, Jacopo, Gabrielle, and Constantino have earned strong praise for clear organization and good humor.

“Everything was organized perfectly. Jacob and Camilla were great and were very knowledgeable of the sites we saw. The wine tasting was awesome and we enjoyed all of the wine that was served. Would highly recommend to anyone visiting Florence to go on this day trip”

Check availability →Read our full review

Half day Chianti Vineyard Escape from Florence with Wine Tastings - Meeting Piazzale Montelungo beside Santa Maria Novella
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Vineyard Tours, Vineyard Tours in Florence, Vineyard Tours in Italy, Wine Tastings, Wine Tastings in Florence, Wine Tastings in Italy, Wine Tours

Half day Chianti Vineyard Escape from Florence with Wine Tastings

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

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53

Ride from Florence to two Chianti estates in a comfortable Wi-Fi coach. Meet the winemakers, visit vineyards and cellars, taste up to eight wines with olive oil, cheese, and balsamic vinegar, then return to Piazzale Montelungo. Guides may include Alex, Lorenza, Cecilia, or Ezgi, though the guide changes by departure.

“Anna our guide was informative and very sweet. The tour was an excellent way to see the Siena area of Tuscany.”

Check availability →Read our full review

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Riding Through Vineyards and Olive Groves
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tastings in Italy, Wine Tours

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145Top rated

Leave Florence by van for a guided bike ride through Chianti’s vineyards, olive groves, villas, and winding country roads. Guides such as Ben, Filippo, Angus, and Alessio lead the route, stop for photos, and help with the hills. Finish at a medieval castle with wine, olive oil, and a Tuscan lunch. E-bikes cost extra.

“After check in at the meeting point, we started with a short van ride to the castle where we were outfitted with well maintained bikes, helmets and water bottles. Ben was a great guide and Lorenzo was great support. We had a good mix of skill levels and all did well. The winery tour at the castle along with the food and wine were very nice at the end. pro tips: - take the bio break before you leave the meeting place as the next one available is after the ride - if you're not a regular cyclist and want to complete the entire ride, consider the e-bike option to…”

Check availability →Read our full review

From Florence: Chianti Tour with Two Wine and Food Tastings - First winery: a personal introduction to Chianti wine
Chianti Wine Tours, Florence Wine Tours, Food, Italy Wine Tours, Tour Reviews, Tours, Wine & Food Pairings, Wine and Food Pairings in Florence, Wine and Food Pairings in Italy, Wine Tours

From Florence: Chianti Tour with Two Wine and Food Tastings

11.Chianti Tour with Two Wine and Food Tastings

★★★★★★★★★★4.5 · 1,205 reviews · 5 hours · from $58

Travel from Florence by air-conditioned coach along the Via Chiantigiana to two family-run organic wineries. Walk through vineyards, tour cellars, and taste Chianti wines with Tuscan snacks. Guides such as Keiko, Maria Louisa, and Christiana add local context. A cooking class, lunch, and four-wine tasting are available with selected options.

“Loved the Tuscany area and the wineries that were chosen for us! We were the last tour of the season and were glad to be able to get into a tour!”

Check availability →Read our full review

From Florence: Private Chianti Hills Tour with Tasting - Radda in Chianti, a small village with time to wander
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Private Wine Tours, Tour Reviews, Tours, Wine Tours

From Florence: Private Chianti Hills Tour with Tasting

12.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours · from $1,166

Travel by minivan from Florence into Chianti for two tastings of three wines each, local meats, cheeses, and olive oil. Visit Radda in Chianti, tour a countryside winery, and enjoy free time for shopping. Guides may include Anna, Chiara, Emma, or Abbie, depending on the date.

“The tour was very well organized and the tour guide, Alessandro, was very knowledgeable. I’d highly recommend this tour.”

Check availability →Read our full review

Chianti Wineries Tour with Tuscan Lunch and San Gimignano - First winery: a personal introduction to Chianti wine
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Lunch Experiences, Tour Reviews, Tours, Wine Tours, Winery Tours, Winery Tours in Florence, Winery Tours in Italy

Chianti Wineries Tour with Tuscan Lunch and San Gimignano

13.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend about eight hours with a small group of up to 16, visiting two Chianti wineries, tasting local wines, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Lorenzo, Christian, Cecilia, and Leonardo are praised for lively stories and good pacing. Round-trip transport from central Florence is included.

“It was a lot of fun and Cecilia was a wonderful guide with a great personality. She made it fun and the whole group were friends by the end of the trip.”

Check availability →Read our full review

Tuscany Day Trip: Chianti & Cooking Class Small Group - Castellina in Chianti: a quick taste of village life
1-Day Tours, Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Tour Reviews, Wine Country Day Trips, Wine Country Day Trips in Florence, Wine Country Day Trips in Italy, Wine Tours, Workshops

Tuscany Day Trip: Chianti & Cooking Class Small Group

14.Tuscany Day Trip: Chianti & Cooking Class Small Group

★★★★★★★★★★4.5 · 770 reviews · 11 hours 30 minutes (approx.) · from $167

Spend about 11.5 hours exploring Castellina, Monteriggioni, San Gimignano, and Certaldo from Florence. The day includes a hands-on Tuscan cooking class, lunch, dessert wine, two wine tastings, and free time in medieval towns. Guides such as Marco and Marta have earned special praise for their warm, helpful approach.

“This was a small group tour. I would recommend to purchase tickets for Siena sites ahead of time so that you save time and not stand in cues. The wine tasting and lunch at Poggio ai Laghi in Monterioggioni was so much fun and the views at San Gimignano were spectacular.”

Check availability →Read our full review

Florence: Chianti Wine Region Vespa or Fiat Topolino Tour - Choosing between the Vespa and Topolino
Chianti Wine Tours, Florence Wine Tours, Italy Wine Tours, Motorbike & Scooter Rentals, Scooter Rentals, Tour Reviews, Tours, Vineyard Bike Tours, Vineyard Bike Tours in Florence, Vineyard Bike Tours in Italy, Wine Tours

Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

15.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours · from $144

Leave Florence by minivan for a guided 35-kilometer ride through Chianti, Impruneta, and Chiocchio. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. After quiet country roads and a medieval village stop, tour a winery, taste wine and olive oil, and share a typical Tuscan meal with guides such as Niccolò, Julia, or Yo.

“Absolutely incredible experience! Niccolo and Julia were amazing guides. You get a little tutorial to learn how to ride the Vespa and then you get to ride the Vespa around Chianti with beautiful views for about 2 hours! The included lunch and wine were great.”

Check availability →Read our full review

New in Chianti Wine Tours

★ 5.0ROMANTIC WINE TOUR FOR 2 – Wine Tour in Chianti (Tuscany)27 reviews
★ 5.0Chianti Wine Tour with LunchFrom $20334 reviews
★ 4.8Chianti Countryside E-Bike Tour w/ Lunch & WineFrom $20344 reviews
★ 4.6Wine Tasting and Dinner in Chianti VineyardsFrom $141192 reviews
★ 5.0Small Group Chianti Wine Tour with LunchFrom $23741 reviews
★ 4.8Great Chianti Wine and Olive Oil Trail with LunchFrom $104160 reviews
★ 4.7Chianti Villages, San Gimignano and Winery TourFrom $19995 reviews
★ 5.0Chianti Hills Bike Tour with Farm Lunch & WineFrom $15232 reviews
★ 4.7Chianti E-Bike Tour with Lunch & Two Wine TastingsFrom $116231 reviews
★ 5.0Chianti E-Bike Tour with Tuscan Lunch & WineryFrom $17542 reviews
★ 4.8Discover Chianti Classico wines with a visit and tasting at ViticcioFrom $4127 reviews
★ 4.9Chianti: Lunch with Wine Tasting at Poggio ai Laghi WineryFrom $4168 reviews
★ 4.7Chianti Wine Tour with 3 Wineries & Tuscan LunchFrom $23436 reviews
★ 4.9Chianti: Wine and Olive Oil Tasting with Cellar TourFrom $3935 reviews
★ 4.8Chianti: Vineyard to Bottle Winery Visit with TastingsFrom $3771 reviews

Keep browsing

Douro Valley Wine Tours60Bordeaux Wine Tours87Cape Winelands Tours39Etna & Volcanic Wine Tours36Champagne Tours110
Scroll to Top

Pick a region

A country, a grape or an afternoon with nothing planned.

The classics

ChiantiDouro ValleyBordeauxChampagneCape Winelands

Kinds of tasting

Wine TastingsCellar VisitsPort LodgesSommelier-LedWine and Cheese

Days out

Wine Country Day TripsWinery ToursVineyard WalksBike the VinesPrivate Days

With a plate

Food PairingsWine and TapasVineyard LunchesWine and Olive OilSunset Pours