10 TOP Things to Do in Chianti Region May 2026

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Most fun & popular experiences in Chianti Region

Tours & day trips

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Gems of Tuscany: Florence & Pisa One Day Excursion from Rome

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Food, drink & nightlife

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The Best of Tuscany in One Day Sightseeing Tour

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Private & custom tours

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Private Wine & Oil Tasting with Lunch

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Classes & workshops

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Florence: Pasta Cooking Class with Unlimited Wine

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Shows & concerts

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Florence: Santa Monaca Church Italian Opera Concert Ticket

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What to do in Chianti Region

Popular places to visit

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.

Night view of the architecture of the small town of Florence, Shanghai

The Mall Luxury Outlet

During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.

Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.

Verrazzano Castle

You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.

Montegufoni Castle

Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the notable monuments and stunning cathedral in this walkable area.

Castello di Albola

You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this romantic area or enjoy its local tours.

Piazza Matteotti

Find out about the history of Greve in Chianti with a stop at Piazza Matteotti. Discover the beautiful countryside in this culturally rich area or enjoy its local tours.

Castle of Brolio

You can find out about the history of Gaiole in Chianti with a visit to Castle of Brolio. Discover the beautiful countryside and cosy cafes in this walkable area.

Croce del Pratomagno

You can learn about the history of Loro Ciuffenna when you stop by Croce del Pratomagno. Discover the countryside in this relaxing area or seek out the campsites.

Explore areas of Chianti Region

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

Il Serraglio

Though Il Serraglio may not have many top sights, you can venture to the surrounding area to see attractions like Antinori nel Chianti Classico and Monastary of Sorelle Clarisse.