Tastings · FLORENCE DRINKS TOURS

Florence Wine Tours: 15 Days Out in the Hills

23 tours  ·  from $41 a head

Chianti is forty minutes away and Montalcino is two hours. These 15 compare the estates each visits, the size of the group and whether lunch is a sandwich or a sitting.

Florence: Chianti Wineries Tour with Wine Tasting - Meeting the coach near Santa Maria Novella
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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 by comfortable coach from Florence to two Chianti wineries for guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Anna, Alex, Martina, and John have been praised for bringing Tuscany’s wine, villages, and farming traditions to life. Expect about 5 to 5.5 hours, with no hotel pickup or lunch.

“The tour was great. We had first a visit to a traditional small vineyard from a Italian family, great wine and food, and the Nona was super nice with us. We saw the grapes plantations, drank wine and they were good and had snacks. Second one was way bigger, so more comercial, but it was super cool to see the difference between them, specially cause the second one was more than 100years old. The guide knew a lot about the region, and she even gave us recommendations about Florence. Everything went well”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - The second estate: more wine and a Tuscan table
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Small-Group Wine Tasting Experience in the Tuscan Countryside

2.Small-Group Wine Tasting Experience in the Tuscan Countryside

★★★★★★★★★★5.0 · 7,392 reviews · 4 hours 45 minutes (approx.) · from $107Top rated

From Santa Maria Novella, ride into Chianti with an English-speaking guide such as Leo, Jonathan, or Matteo. Visit two wineries, taste six or more regional wines, sample olive oil and Tuscan specialties, and compare estates, cellars, and winemaking styles. The roughly 4-hour-45-minute trip gives you countryside time without consuming a full day.

“We had the best time with Leo, the 2 wineries we stopped at were unbelievable. Bonus, you get to meet so many amazing people on the journey!”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Wine tasting, explained without the lecture
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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

3.SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

★★★★★★★★★★5.0 · 5,088 reviews · 7 to 9 hours (approx.) · from $157

Ride from central Florence in an air-conditioned 4x4 with an English-speaking sommelier. Choose a 7-hour Chianti outing, a sunset dinner, or longer routes to Brunello and Montepulciano. Expect family wineries, cellar visits, olive oil, salumi, cheese, pasta, and generous countryside views.

“Guide was informative and fun. The wines were good as was the food served. The grounds and estate were lovely. Met lovely people from across the world and had great conversations. Only adults on this tour but they were of all ages. Highly recommend”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Charcuterie in a 12th-century cellar
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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

4.Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

★★★★★★★★★★5.0 · 5,015 reviews · 3 hours 30 minutes (approx.) · from $149

Spend about 3.5 hours eating and drinking around Florence’s Oltrarno district. You’ll sample Prosecco, four Tuscan wines, cheese, charcuterie, gnudi pasta, soup, wild boar stew, a Negroni, and artisan gelato. Guides such as Sara D., Martino, Antonella, and Dimitri add local stories, while the group stays small at 13 people or fewer.

“Wonderful tour, great food and wine, a nice way to explore this interesting neighborhood across the Arno. Antonella was our guide — a funny, lively personality who made everyone laugh and have a really good time. Highly recommend her and the tour. A delightful way to spend an evening!”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena, where the day begins with medieval drama
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

5.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Spend 12 hours touring Tuscany from Florence by air-conditioned coach. Walk Siena with a local guide, visit its Duomo, enjoy a farmhouse lunch and four-wine tasting at a Chianti winery, then explore San Gimignano and Pisa. Guides such as Sara, Alessandro, Alex, and Giancarlo are known for lively commentary and careful timekeeping.

“The tour was amazing! We had Alex as our tour guide and he did an incredible job. From the minute we drove out of Florence he spoke to the history of every city we visited and everything we saw on the way there. This was perfect as it gives context to what you’re seeing. Everything on the tour was very well thought out, we couldn’t be any more pleased with how everything went. I would strongly recommend 100%. Thank you Alex!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and the town of towers
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

Spend 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, a Chianti winery lunch and tasting, and guided Siena options. Guides such as Sandro, Marta, Ricardo, and Ilaria have earned praise for clear, friendly leadership. Choose the cathedral upgrade if Siena art matters to you.

“Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks to AARON and LILY for being our guide and to PLACIDO for driving us to our destinations safely.”

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Chianti Wine Tour from Florence - The second stop in Sienese Chianti Classico
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Chianti Wine Tour from Florence

7.Chianti Wine Tour from Florence

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

Leave Florence by air-conditioned coach and follow the Via Chiantigiana through vineyards, olive groves, and hill towns. Visit two organic wineries, taste six or seven Tuscan wines with local foods, and tour vineyards and cellars with wine makers. English and Spanish tours are available, with optional cooking and lunch upgrades.

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

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From Florence: Small Group Wine Tasting Tour to Tuscany - The first winery: wine, olive oil, and cellar traditions
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From Florence: Small Group Wine Tasting Tour to Tuscany

8.Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Leave Florence by air-conditioned minibus for two Chianti Classico wineries. You will taste six wines, olive oils, cheese, salami, cold cuts, and bruschetta while local hosts explain cellar methods and Tuscan traditions. Guides such as Jason, Jonathan, Leo, and Raffaele are known for lively commentary, music, and practical Florence tips.

“This was a great relaxing evening. This is a nice tour for when you need a break from the museums and running to different spots. Although more insight into the wine making process would have been great, we knew what we signed up for. The wine was delicious, but we took away a new appreciation of really good aged local balsamic. It was terrific with the Pecorino cheeses and paired nicely with the classicos. Highly recommend!”

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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch - A Chianti winery lunch with local wine
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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch

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

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

From Florence, ride through the Tuscan countryside to San Gimignano, a Chianti winery, Siena, and seasonal Monteriggioni. You get free time, local guides, three wines, Vin Santo, and a three-course lunch. Guides such as Marta, Ricardo, Sandro, and Alessandra are praised for clear directions and good humor, though Siena time can feel short.

“The trip was great! A very easy day out without feeling rushed or feeling like travel time was long. Coach was comfortable and ride was smooth. Guide Hilary was professional, yet enthusiastic. Lunch and wine at vineyard was excellent. before the trip i was a little fearful due to long duration. but i thoroughly enjoyed myself and wished did not end :)”

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From Florence: Chianti Half-Day Wine Tour with Tasting - Poggio ai Laghi and the first tasting
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From Florence: Chianti Half-Day Wine Tour with Tasting

10.Chianti Half-Day Wine Tour with Tasting

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

Leave Florence by tram and air-conditioned coach for two Chianti wineries, seven wine tastings, olive oil, balsamic vinegar, salami, cheese, and bruschetta. You will also stop at Monteriggioni. Guides such as Luca, Marco, Tula, and Alicia have led recent departures, while the 75-minute winery visits can feel brisk.

“Excellent service, right on time. Lyla and Claudio were fun and entertaining. The bus was clean. The wineries a little rushed, not much time to enjoy the vineyards. But the wineries personal excellent as well. I highly recommend.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Piazzale Montelungo and the 40-minute ride south
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

11.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 with an English-speaking guide, taste up to six to eight wines with olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have earned praise for clear, friendly explanations, though the group may reach 43 people.

“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!”

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From Florence: Tuscany Wine & Food Tour with Guide - First winery: learn how Chianti becomes wine
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From Florence: Tuscany Wine & Food Tour with Guide

12.Tuscany Wine & Food Tour with Guide

★★★★★★★★★★4.9 · 1,746 reviews · 8 hours · from $175

Travel from Florence into Chianti with an English-speaking guide such as Leo, Jason, or Jonathan, depending on the date. Visit three organic wineries, taste red wines, olive oil, and balsamic vinegar, enjoy a Tuscan lunch, and stop in Greve. Expect winding roads, stairs, and a full day of food and wine.

“We had such a blast on this tour - Nino and Jonathan were the best!! The bus was comfortable and the three winery stops were incredible, each one better than the last. We also loved the free time in Greve, which is an adorable town. Our group bonded and had a fantastic time. We felt like the day flew by and was wonderful value for money. A great way to see Tuscany!”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - The one-mile hill you need to plan for
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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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

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

Leave Florence by van for a roughly 12-mile ride through Chianti’s vineyards, olive groves, villas, and country roads. Guides including Ben, Filippo, Angus, and Alessio lead the route, with photo stops, a castle wine tour, olive oil tasting, and Tuscan lunch. Regular bikes are included. E-bikes cost extra and require advance notice.

“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…”

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From Florence: Chianti Tour with Two Wine and Food Tastings - Following the Via Chiantigiana into the hills
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From Florence: Chianti Tour with Two Wine and Food Tastings

14.Chianti Tour with Two Wine and Food Tastings

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

Travel from Florence along the Via Chiantigiana to two family-run organic wineries in Chianti Classico. Expect cellar visits, vineyard walks, guided tastings, olive oil and Tuscan snacks, and a friendly English or Spanish-speaking guide. The optional morning cooking class adds lunch and four premium wines.

“We really enjoyed the tour. Once on the bus it was a very easy and relaxing trip. Our bus tour guide Keko was very informative. She pointed out a place with the Verrazzano family name on it that's connected to the Verrazzano bridge from my hometown NYC. The two wineries were great altho the second one was my favorite. Our tour guides for the winery I believe one of their names was Fernando (probably wrong but he had black hair) he did our tasting and the other guy's name sheesh can't remember started with an "A" (he had red hair) he started the tour either way they both were fantastic…”

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From Florence: Val D'Orcia Tour with Wine Tasting - Montalcino and the first taste of Brunello
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From Florence: Val D’Orcia Tour with Wine Tasting

15.Val D’Orcia Tour with Wine Tasting

★★★★★★★★★★4.6 · 1,106 reviews · 11.5 hours · from $108

Spend 11.5 hours in Tuscany with a guide such as Alex, Julia, or Constantino, visiting Montalcino, Pienza, and Montepulciano. Ride a comfortable coach, tour two wineries, taste Brunello and Vino Nobile, sample Pienza’s Pecorino, and enjoy free time for lunch, photos, and wandering. Expect hills, stairs, and a full day.

“We loved the whole day trip to the wineries and the Tuscan towns of Montelcino, Pienza and Montepulciano. Pienza was definitely a high light town for us. We hoped there were more wineries to visit but the ones we did see were lovely!”

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Just poured: Florence Drinks Tours

★ 4.0Chianti Delights: A Tale Of Two Wineries With A Vineyard DinnerFrom $106324 reviews
★ 4.5Chianti Vineyards Escape from Florence with Two Wine TastingsFrom $53280 reviews

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