Surrounded by the warm colors of nature, every Chianti village lights up: tastings, evenings and conviviality make this area even more magical
With the arrival of fine weather, Chianti awakens amid blossoming vineyards, bustling villages and the scent of wine preparing to tell of a new vintage. Spring and summer 2025 will be full of unmissable events for those who want to experience the area through original experiences, walks through the hills and tastings of local excellence.
May: wines, villages and open wineries
The month of May kicks off the season with events that combine the beauty of Chianti landscapes with wine-making excellence. On May 17 and 18, Montefioralle hosts “The Wines of the Castle,” a weekend of tastings in the courtyards and gardens of the medieval village, amid flower-filled vistas, ancient stones and rows of vines that embrace the village.
The following weekend, May 24 and 25, is the turn of “Radda nel Bicchiere,” a symbolic event in the village of Radda, where wineries open their best labels to onlookers and enthusiasts, with the scent of Chianti Classico mingling with that of roses.
Also returning at the same time is the long-awaited “Cantine Aperte” event organized by the Movimento Turismo del Vino, which on May 24 and 25 offers an opportunity to discover the productive heart of Chianti, meet the winemakers and experience the magic of vineyards in bloom and family stories that have been passed down for generations.
Learn more about the Chianti villages that host the most beautiful events.
Tastings among the village streets during Radda in the Glass.
Photo: Pro Loco Radda in Chianti
June: traditions, scents and flavors
As the new month approaches, from May 31 to June 2, Lamole hosts the 22nd edition of “I Profumi di Lamole,” where the delicacy of blooming irises is the setting for a tasting of high altitude Chianti Classico, produced from historic vineyards cultivated on stone terraces. The air is scented with iris, broom and moist earth: the beauty of the landscape blends with that of the glass.
Following this, from June 6 to 9, the village of Castellina in Chianti hosts the traditional Pentecost, a widespread event in the streets of the village with food stands and tasting stalls that transform the historic center into a small street party, including bruschetta, local cured meats and walking glasses.
On June 14 and 15, in Lucolena, red wine gives way to extra virgin olive oil: the Sagra della Schiacciata all’Olio is celebrated, where the simplicity of local flavors meets the conviviality of village festivals, including live music, outdoor tables and the smell of freshly baked bread.
July and August: tastings under the stars
During the warmer months, Chianti invites you to experience its summer nights with special events. In Castellina in Chianti, there is the long-awaited “Goblets of Stars” event (scheduled from July 25 to August 24), which combines local wine with tastings under the starry sky, amid music and a unique atmosphere. This is the time when villages come alive at sunset, squares are transformed into outdoor living rooms, and every glass becomes an opportunity to celebrate summer. The hills, with their long shadows and after-dinner silences, become the perfect stage to be enchanted.
September, the grand finale of Chianti
Finally, in September, some of the most anticipated events include the return of “Vino al Vino” in Panzano, which brings local producers to the square, “Montefioralle Divino,” a wine celebration within the walls of Italy’s most beautiful village, and “Radda nel bicchiere” in the village of the same name.
Grand finale in Greve in Chianti, Sept. 11-14, with Expo Chianti Classico, the area’s signature event with tastings and meetings dedicated to the excellence of the Black Rooster.
Expo Chianti Classico, the symbolic event of wine in its territory.
Photo: Municipality of Greve in Chianti / Expo Chianti Classico
Tastes, steps and encounters among the hills
From spring to early fall, each appointment is an opportunity to discover Chianti on the road, being enchanted by breathtaking views, timeless villages and shared glasses of wine.
And it is also the perfect time to entrust yourself to the expert hands of WeHike, for a guide who can help you discover even the lesser-known aspects and enjoy authentic experiences, at the table, in the winery and on the Chianti trails. Walking among the rows, listening to history, discovering every nuance of this unique territory.
Check out the experiences that WeHike offers and discover Chianti like you’ve never done it before.
Events summary: what to do in Chianti from May to September
May
- I Vini del Castello
📍 Montefioralle (Greve in Chianti)
📅 May 17-18, 2025
🎟️ Tasting of local wines in the courtyards of the medieval village.
🔗 Event details - Radda in Chianti
📍 Radda in Chianti
📅 May 24-25, 2025
🎟️ Tasting of wines from local wineries in the streets of the village.
🔗 Official website - Cantine Aperte
📍 Various locations in Chianti
📅 May 24-25, 2025
🎟️ Tours and tastings at wineries that are members of the Wine Tourism Movement.
🔗 Event information
June
- I Profumi di Lamole
📍 Lamole (Greve in Chianti)
📅 May 31-June 2, 2025
🎟️ Chianti Classico tastings among blooming irises and panoramic terraces.
🔗 Event details. - Bevo Castellina
📍 Castellina in Chianti
📅 June 6-8 2025
🎟️ Food stands and tastings in the historic center. - Festival of Schiacciata all’Olio
📍 Lucolena (Greve in Chianti)
📅 June 14-15, 2025
🎟️ Festival dedicated to schiacciata all’olio with music and conviviality.
🔗 Event details
July – August
- Calici di Stelle
📍 Castellina in Chianti
📅 Dates to be confirmed (July 25-Aug. 24, 2025)
🎟️ Evening tastings under the stars with live music.
🔗 Event information
September
- Vino al Vino
📍 Panzano in Chianti
📅 Third weekend of September 2025
🎟️ Meeting with local producers and tastings in the piazza.
🔗 Official website - Montefioralle Divino
📍 Montefioralle (Greve in Chianti)
📅 Last weekend of September 2025
🎟️ Wine festival with tastings in the medieval village.
🔗 Event details - Expo Chianti Classico
📍 Greve in Chianti
📅 September 11-14, 2025
🎟️ Exposition of Chianti Classico producers with tastings and meetings.
🔗 Official website