Book Wine Tours & Tastings in Chianti

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Day Trips

From Florence: Chianti Wineries Tour with Wine Tasting

What to bring

Wear comfortable walking shoes as winery visits may include short uphill walks.

What’s not allowed

Guests under 18 years old are not allowed to participate in wine tastings and must be accompanied by at least one adult.

Accessibility

This experience is not accessible by wheelchair or pram/stroller.

Additional information

Wi-Fi may not work properly in certain parts of the Chianti countryside due to limited network coverage.
The tour operates with a regular group of up to 45 guests.

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Free cancellation

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5 hrs

Transfers available

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Guided Tours

From Florence: Chianti Countryside & Olive Grove Semi-Private Tour with Lunch & Gourmet Pairings

Tip: If you're a foodie, ask for pairing recommendations! Mill staff can often suggest specific dishes or recipes that highlight the best qualities of their olive oil.
This experience is not accessible by wheelchair and pram/strollers.
For safety reasons, guests under 18 are not permitted to take part in the tasting experience.
Guests under 18 can join the tour if they are each accompanied by at least one adult.
Please inform in advance if you have any food allergies or intolerances. Vegetarian needs can also be accommodated with prior notice.

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Free cancellation

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4 hrs 30 mins - 9 hrs

Transfers available

Meals included

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Day Trips

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Four sides of Tuscany in one day — art cities, a Chianti winery tasting, Tuscan lunch & medieval hilltop villages.

Full day out to: Pisa, Chianti, San Gimignano, and Siena from Florence on a full-day scenic journey.
You’ll get: Travel in an AC coach with Wi-Fi and a multilingual tour leader, free time in Pisa, Siena, and San Gimignano, plus a Chianti winery visit with 3 wine tastings and a traditional Tuscan lunch.
Pisa: Walk through Piazza dei Miracoli, admire the Cathedral and Baptistery, and see the world-famous Leaning Tower, with time to explore at your own pace.
Chianti: Stop at a local winery nestled in rolling hills for a relaxed Tuscan meal paired with regional wines and vineyard views.
San Gimignano: Wander cobbled streets lined with medieval towers, browse artisan shops, and soak in views of this UNESCO-listed hill town.
Siena: Discover the charm of this historic city, from Piazza del Campo to its Gothic cathedral, with optional guided tours that dive deeper into its traditions.
Upgrades: Add a guided tour of Siena, include Cathedral access, or climb the Leaning Tower of Pisa for panoramic views.

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Free cancellation

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11 hrs 30 mins - 12 hrs

Guided tour

Transfers available

Meals included

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Guided Tours

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Two of Tuscany's finest medieval towns and a Chianti winery, without the whistle-stop rush.

Day out to: Siena, San Gimignano, and Chianti on a scenic day trip from Florence.
You’ll get: Round-trip AC coach transfers with Wi-Fi, a multilingual tour leader, free time in Siena and San Gimignano, plus a Chianti winery visit with 3 wine tastings.
Siena: Wander through a UNESCO-listed old town filled with Gothic architecture, lively squares, and historic charm, or upgrade for a guided walk.
Chianti: Head into Tuscany’s wine country for a relaxed winery stop, where you’ll taste 3 regional wines surrounded by vineyard views.
San Gimignano: Explore the iconic “Town of Towers,” known for its medieval skyline, cobbled streets, and artisan shops.
Upgrades: Add a guided tour of Siena to uncover the stories behind its historic streets, Piazza del Campo, and local traditions.

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Free cancellation

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10 hrs 30 mins - 11 hrs 30 mins

Transfers available

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Guided Tours

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

What to bring

Comfortable walking shoes
Valid photo ID
Clothing that covers shoulders and knees for Siena Cathedral (if visiting)

Accessibility

Not wheelchair accessible
Not suitable for prams/strollers

What’s not allowed

The wine tasting experience is restricted for guests under the age of 18 years.
Guests under 18 can join the tour if they are each accompanied by at least one adult.

Additional information

Please note that the order of visits is subject to change.

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Free cancellation

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9 hrs - 11 hrs

Transfers available

Meals included

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Day Trips

From Florence: Small Group Pisa, Siena, San Gimignano & Chianti Day Trip

Travel Tuscany’s highlights in a small group of just 20 guests for a more relaxed, personal day out.

Day out to: Pisa, Siena, San Gimignano, and the Chianti wine region on a scenic small-group journey from Florence.
You'll get: Travel with a maximum of 20 guests, round-trip AC coach transfers, onboard Wi-Fi, a local tour leader, free time in Pisa, Siena, and San Gimignano, a Chianti winery visit with 3 wine tastings, and a traditional Tuscan lunch.
Pisa: Enjoy free time to admire the Leaning Tower, stroll through the Square of Miracles, and explore the city at your own pace.
Siena: Wander medieval streets, discover Piazza del Campo, and soak up the atmosphere of one of Tuscany's most captivating cities.
San Gimignano: Explore a UNESCO-listed hill town famed for its medieval towers, artisan shops, and sweeping countryside views.
Upgrades: Choose the Siena guided tour option to uncover the stories, traditions, and architecture that shaped this historic city.

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Free cancellation

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11 hrs 30 mins - 12 hrs 15 mins

Guided tour

Transfers available

Meals included

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Day Trips

From Florence: Siena and Chianti Day Trip with Dinner & Regional Pairings

This experience is not accessible by wheelchair and pram/strollers.
Please inform in advance if you have any food intolerances or allergies.
English and Spanish tours are available by default. A minimum of 4 participants is required to book an excursion in Italian, Portuguese, or French.
Comfortable shoes are recommended.
Minors below the age of 18 will not be served drinks.

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Check availability

Free cancellation

Book now, pay later

7 hrs

Guided tour

Transfers available

Meals included

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