Category Tuscany Wine Country from Florence

Florence · TUSCANY WINE COUNTRY FROM FLORENCE

The 15 Best Tuscany Wine-Country Tours from Florence

39 experiences compared

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Coach time to Siena: useful context before the first cobblestones

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Editor's first choice

Florence day trip to Siena, San Gimignano and Pisa, with Siena Cathedral and a Chianti winery lunch plus wine tasting.

“Prob our least favorite excursion we have done this trip. Trip should be condensed to one stop (like Pisa) and maybe lunch/winery. However, our Tour guide was EXCELLENT. It’s just not the best trip we’ve ever done by far.”

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Florence: Chianti Wineries Tour with Wine Tasting

Florence: Chianti Wineries Tour with Wine Tasting - Two Cantinas, One Connected Day: How the Winery Stops Feel

Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside - The Drive Through Chianti Hills: Wi-Fi, Guide Talk, and Scenic Stops

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

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

Small-group Chianti wine tasting from Florence: visit two estates, tour vineyards, taste 6 wines plus olive oil, and enjoy Tuscan bites.

“Beautiful day out! Both wineries were stunning and we learnt heaps. Got given 4 glasses at each winery. Better to book the tour in second half of the day as you see sunset over the wineries which is incredible!”

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

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Stop one: boutique winery tastings with olive oil and cured meats

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

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

Off-road wine safaris from Florence with family wineries, expert tastings, olive oil and salumi pairings, plus a full Tuscan meal.

“Sara was an amazing and knowledgeable guide with a combination of wine and historical information! Fabio was a great driver through the rainy winding roads and made the journey more comfortable and fun! We looked at a lot of tours and so happy we picked this one!”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Getting Started at Piazza Santo Spirito

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

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

Florence at sunset, all food, wine, and a Negroni tutorial. Walk Oltrarno with tastings at local wine windows and trattoria.

“This was a fabulous evening tour. We learned so much about the food, we’re taken to small and authentic places. I would suggest doing this early in your stay as you would go back to some of the restaurants for a meal. The little bits of food were more than satisfactory so don’t eat a big meal before you go.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena walking tour: Piazza del Campo, the Duomo, and the medieval details

6.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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

From Florence, tour Siena, San Gimignano, Pisa and a Chianti winery lunch with wine tasting, plus optional Leaning Tower entry.

“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, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Stop 1: San Gimignano, the town of towers

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

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

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.”

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Chianti Wine Tour from Florence

Chianti Wine Tour from Florence - Why the Via Chiantigiana Drive Is Half the Point

8.Chianti Wine Tour from Florence

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

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”

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From Florence: Small Group Wine Tasting Tour to Tuscany

From Florence: Small Group Wine Tasting Tour to Tuscany - Piazzale Montelungo meeting point: find it fast, start relaxed

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

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Meeting point in Florence: Piazzale Montelungo and the on-time rule

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Half day Chianti Vineyard Escape from Florence with Wine Tastings - Two Wineries, One Afternoon Formula

From Florence: Tuscany Wine & Food Tour with Guide

From Florence: Tuscany Wine & Food Tour with Guide - The Chianti Drive from Florence: Wi-Fi On Board and Motion Reality

12.From Florence: Tuscany Wine & Food Tour with Guide

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

Small-group Chianti wine and food tour from Florence with 3 winery tastings, Tuscan lunch, and a break in Greve in Chianti.

“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

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - The Chianti countryside ride: olive groves, villas, and photo stops

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

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

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…”

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From Florence: Val D’Orcia Tour with Wine Tasting

From Florence: Val D'Orcia Tour with Wine Tasting - Getting started in Florence: meeting point and coach comfort

From Florence: Chianti Wine Tour with Tastings

From Florence: Chianti Wine Tour with Tastings - Where you meet: Stazione Montelungo or Piazzale Montelungo