Category Chianti Wine Tours

Italy · CHIANTI WINE TOURS

The 14 Best Chianti Wine Tours from Florence

14 tours

Chianti begins forty minutes south of Florence and most days out take in two or three estates. Below are the 14 best, with how many cellars each visits, whether lunch is included or an afterthought, group sizes, and whether someone else is doing the driving on those roads.

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

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa Cathedral Area, Cemetery Views, and the Leaning Tower Plan

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

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

One day in Tuscany by bus: Pisa, San Gimignano, Siena, and Chianti, with winery lunch, wine tasting, and optional Leaning Tower tickets.

“I enjoyed every moment of this tour. Barbara is an amazing guide and told us everything about the places we visited and where to find the best gelato and coffee (and bathrooms😅). For the Siena tour, Chiara was an amazing tour guide and the lunch at Poggio Ai Laghi was paired with some of the best wines I tasted. The whole tour was an amazing experience and I recommend it to anyone who wants to see the highlights, just so they can visit those places by themselves again and fully enjoy everything about Toscana.”

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

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano Towers: 2 Hours to Wander Without Feeling Trapped

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

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

San Gimignano towers, Monteriggioni walls, and Chianti wine lunch, then Siena’s Duomo and squares in one long, well-paced day trip.

“Great trip. Lots of walking. I had 7 miles logged on the smart watch. It was a long day. Unfortunately we got to San Gimignano by 9 . Most of the top sites didn’t open until 10;30 or 11. We left at 10:45 for the next stop. Most of the shops on the Main Street were open so if you don’t like shopping this might be disappointing for you. The lunch in Siena was great, as was The guided tour and the Cathedral. So I would definitely recommend doing the tour and the cathedral in Siena as part of your options.”

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

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Getting to Piazzale Montelungo without stress

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena first: Piazza del Campo, Santa Maria Assunta, and real time to wander

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni Hilltop Fortress, Fast Photos and Optional Wall Time

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

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Meeting point reality, bus timing, and how to not lose the day

From Florence: Chianti Half-Day Afternoon Tour

From Florence: Chianti Half-Day Afternoon Tour - Getting to Villa Costanza: Tram T1.3 and the Green-Scarf Match

9.From Florence: Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55

Half-day Chianti from Florence with two wineries, seven wine tastings, olive oil and balsamic pairings, plus Monteriggioni free time.

“The exact meeting spot was hard to find. We almost missed the tour. All others have an exact spot to meet, with special instructions. If it would have said "Bus/Train station, in the parking lot, look for guide with a green jacket" would have been helpful.”

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

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Pisa at Piazza dei Miracoli: what you really get in 15 minutes

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Half day Chianti Vineyard Escape from Florence with Wine Tastings - The Chianti Road Viewpoint: Why the Scenery Matters Even When You Only Stop Briefly

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

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

Half-day Chianti escape from Florence: two winery stops, cellar walks, Chianti tastings with olive oil and cheese, plus scenic views.

“The tour is incredibly well organized and timely. I did feel like the wineries we visited were a little stingy with the amount of wine/food that was offered; however, I do think this tour is well worth it for the price.”

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

Chianti Vespa Tour with Lunch from Florence & E-car Option - Safety briefing, practice rides, and what to expect once you start driving

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Bikes, Safety Briefing, and the Real Shape of the Hills

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

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

Cycle Chianti hills from Florence, then sip wine and olive oil at a medieval castle with lunch, small group, English guides.

“This bike tour was amazing! Tour guides were excellent from start to finish. Bikes were well greased and mechanics worked well to shift appropriately riding up and down the hills. Castle tour was cool - we were able to see where they store the barrels of wine (Italian and French oak barrels) and learn about the process of wine making, olive oil, and history behind the castle. The tasting of the wine was delicious paired with a robust pasta lunch!”

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

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence - Stop 1, Tenuta Riseccoli: Organic Hilltop Winery and Olive Oil Tasting

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

★★★★★★★★★★5.0 · 1,269 reviews · 8 hours (approx.) · from $180

A small-group Chianti Classico day trip from Florence with 3 winery visits, tastings, and a Tuscan lunch, plus a Greve village break.

“Excellent. Daniele as tour guide and Alessio as driver are a great team. The wineries visited were beautiful and hospitable, and the wine was good. I learned a lot about Chianti wine.”

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