15 Best Tuscany Wine Tasting Tours In Florence

Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

Florence: Chianti Wineries Tour with Wine Tasting

/ June 1, 2026

1.Florence: Chianti Wineries Tour with Wine Tasting

Half-day Chianti wine tour from Florence with two winery visits, tastings of Chianti and pairings, plus vineyard views and easy coach transport.

Small-Group Wine Tasting Experience in the Tuscan Countryside

/ June 1, 2026

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

Small-group Chianti Classico tour from Florence with two wineries, 3+3 wine tastings, olive oil, Tuscan bites, and free Wi‑Fi.

★ 5.0

“We visited two gorgeous wineries, enjoyed amazing wine, and had the best tour guide! Really wish I had bought the wine, vinegar, and olive oil to take home.”

7,392 reviews4 hours 45 minutes (approx.)From $107.63by Prestige Rent

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1-Day Tours, Florence, Lunch Experiences, Pisa Day Trips, Siena & San Gimignano Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

/ June 1, 2026

3.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence day trip: Siena, San Gimignano & Pisa, plus winery lunch with wine pairing. Coach tour, free time, Wi‑Fi.

★ 4.5

“It is a wonderful tour and the price is reasonable.”

6,006 reviews12 hours (approx.)From $78.60by Ciao Florence Tours Srl

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Florence, Food & Drink, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

Off-road Tuscan wine safaris from Florence with 4WD vineyard drives, guided tastings, olive oil, and farm-to-table meals.

★ 5.0

“I 100% recommend this tour. The places we visited were beautiful, and the food was excellent. It is definitely worth it, so don’t think twice.”

5,088 reviews7 to 9 hours (approx.)From $157.21by Walkabout Florence Tours

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Evening Experiences, Florence, Food, Food & Drink, Food & Wine Tours, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

/ June 1, 2026

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

Florence Sunset Food and Wine Tour with Prosecco, four Tuscan wines, Negroni making, wine-window stops, and artisan gelato over 3.5 hours.

★ 5.0

“We took the Florence small group food and wine tour and had the most amazing time. Our guide, Antonella, was incredible! Knowledgeable, professional and funny, she provided the perfect blend of historical perspectives, cultural insights and several dashes of humor to make a wonderful experience even more fantastic. What a great tour, highly recommended if…”

5,015 reviews3 hours 30 minutes (approx.)From $149.95by Florence Food Tours by Eating Europe

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1-Day Tours, Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

San Gimignano towers, Chianti winery lunch and wine tasting, and Siena’s Duomo and Campo—an 11-hour coach day from Florence.

★ 4.5

“Too long too many directions. Too long in Siena. Restaurant was below average Felt like cattle being herded in”

4,432 reviews11 hours (approx.)From $83.27by CAF Tour and Travel

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Chianti Wine Tours, Florence, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

Chianti Wine Tour from Florence

/ June 1, 2026

7.Chianti Wine Tour from Florence

Florence to Chianti: two organic winery visits, vineyard walks, cellar tastings with local food, plus scenic Via Chiantigiana views.

★ 4.5

“The half day tour was fun but was a bit chaotic going back and forth between Italian, English and Spanish. The group was divided into groups once we reach the wineries but was so loud at the first stop I couldn’t understand a word our guide was saying. The second stop, each group was a…”

3,979 reviews5 hours (approx.)From $59.13by CAF Tour and Travel

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Florence, Food & Drink, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Wine Tours

From Florence: Small Group Wine Tasting Tour to Tuscany

/ June 1, 2026

8.From Florence: Small Group Wine Tasting Tour to Tuscany

Half-day from Florence to Chianti Classico: two winery cellar tours, 6 wine and olive oil tastings with Tuscan snacks, small group.

★ 4.9

“Jason was a fantastic guide. He made a great tour even more fun. The wineries were beautiful.”

3,902 reviews4.5 hoursFrom $105by Prestige Rent - Tours in Italy

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Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

Florence day trip to San Gimignano, Siena and Chianti: UNESCO towns, optional cathedral visit, and lunch with a three-wine tasting.

★ 4.6

“Martha, our tour guide was excellent. She had great knowledge of the towns we visited and provided us with all information we needed to know. She was very friendly and approachable. A big thanks to our driver Ferdinand, as well.”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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Chianti Wine Tours, Florence, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

Half day Chianti Vineyard Escape from Florence with Wine Tastings

/ June 1, 2026

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

Half-day Chianti wine escape from Florence with two winery stops, vineyard walks, cellar visits, and tastings on the Chianti Road.

★ 4.5

“It is a VERY big tour group - like 40-50 people (fills up a large tour bus), so it is quite hard to feel very engaged / involved. The winery tours were also quite high level, so I didn’t feel like I learnt a lot about the Chianti wine region. We tasted 3 wines at…”

2,196 reviews5 hours (approx.)From $53.10by Ciao Florence Tours Srl

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Chianti Wine Tours, Cycling Tours, Florence, Food & Drink, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Vespa, Bike & Golf Cart Tours, Wine Tours

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

/ June 1, 2026

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

Cycle through Chianti hills from Florence, stop for photos, then taste Chianti wine and olive oil at a medieval castle with lunch.

★ 5.0

“This tour was an amazing experience in the Tuscan country side. Angus did a great job leading us through the country side on bikes. He stopped at several points for photo opportunities and share info about the area. The wine tasting and lunch at the castle was a perfect end to the morning. The biking…”

1,300 reviews6 hours (approx.)From $145.12by Tuscany Bike Tours

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Florence, Food & Drink, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Wine Tours

From Florence: Val D’Orcia Tour with Wine Tasting

/ June 1, 2026

12.From Florence: Val D’Orcia Tour with Wine Tasting

Val d’Orcia day trip from Florence: Brunello + Vino Nobile tastings, pecorino, and Montalcino, Pienza, Montepulciano.

★ 4.6

“We were given extra 2 minute to take photo of the Gladiator iconic place. Alejandro was very considerate and prompt, our driver was amazing too”

1,106 reviews11.5 hoursFrom $108by Ciaoflorence Tours & Travel

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Chianti Wine Tours, Florence, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

From Florence: Chianti Wine Tour with Tastings

/ June 1, 2026

13.From Florence: Chianti Wine Tour with Tastings

Half-day Chianti tour from Florence: visit 2 organic wineries with tastings, scenic hills, and local food like pecorino and olive oil.

★ 4.4

“This tour was awesome, our guide Alessia (Alexa) was perfect and we had a fantastic experience at both wineries where the staff were friendly, funny and educated us about the different wines! Highly recommend!! We also met some great travelers in our group!”

1,025 reviewsFrom $62.63by CAF Tour & Travel

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Florence, Siena & San Gimignano Tours, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Wine Tours

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

/ June 1, 2026

14.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Florence Chianti road day trip with tastings at 2 wineries, Vernaccia near San Gimignano, plus 1.5 hours to wander towers and medieval streets.

★ 5.0

“Emanuele was an excellent guide/driver. Both wineries were fantastic and San Gimignano was lovely. A perfect day in Tuscany. Would definitely recommend this tour.”

1,007 reviews7 hours (approx.)From $229.77by Italy on a Budget tours

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Chianti Wine Tours, Florence, Lunch Experiences, Siena & San Gimignano Tours, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours

Chianti Wineries Tour with Tuscan Lunch and San Gimignano

/ June 1, 2026

15.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

Chianti wineries plus a guided San Gimignano visit, Tuscan lunch, wine tastings, and Florence’s Piazzale Michelangelo viewpoint from one easy day trip.

★ 5.0

“Our guide Daniel was amazing. It was a lovely day at the wineries and touring San Gimignano. The wine was amazing and so were the snacks and lunch we were provided.”

793 reviews8 hours (approx.)From $229.77by Chianti Wine Tour

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