What to do in Chianti. A guide to the best experiences

20 May 2024 | Activities

It is all to be experienced and explored. But what to do in Chianti to best appreciate it? Here are some suggestions on places and activities to enjoy these hills at any time of the year.

Chianti, in the heart of Tuscany, is world-renowned for its enchanting landscapes, places ofart and culture, and ancient and prestigious wine and culinary traditions. Such a panorama of excellence makes it the ideal place for all those seeking fullfilling and slow tourism, all year round.

From the rolling hills covered with vineyards in summer to the fascinating trails in the colors of autumn, from spring blossoms to winter markets, the region offers a perfect retreat from modern busy life. In addition to enjoying the natural beauty, visitors who choose to spend a weekend or an entire week here can discover works of art, historic mansions and ancient architecture, festivals and customs, wines and typical dishes that tell stories of a bygone era.

discover what to do in chianti with wehike's guide to the best experiences
The view of the Chianti hills in summer with the bright green vineyards

Chianti, a paradise for hiking and outdoor activities

Chianti attracts hikers from all over the world with its variety of trails. From relaxing walks through vineyards to more challenging hikes along mountain ridges, there is something for every skill level and suitable for every month of the year.

The activities then are always accompanied by a touch of magic: whether it is the story of a monastery, the legend that tells how Siena and Florence challenged each other among these valleys, or an anecdote about the recipes for sweets that are prepared in winter. For those who like something more eventful and adrenaline-pumping, river trekking and rafting on the Elsa River (these, however, are best done in summer…), which are particularly popular with groups, those who choose a bachelorette party or a retreat to do team building . Each experience is an exciting mix of adventure and breathtaking natural vistas, accompanied by expert guides.

team building experiences in tuscany with trekking in the chianti hills
A group during a team building experience in the Chianti hills.

Stroll and discover among the villages and castles of Chianti

Many are the events that have had their theater among the Chianti villages, such as Castellina, Radda, Lamole, Greve in Chianti or Montefioralle, and their medieval fortresses, true treasure troves of the region’s history. Among the tours you can choose for a Chianti vacation, visits to ancient villages and castles, mills and historical re-enactments allow you to relive the events of centuries past firsthand.

And each season has its own charm, with spring breezes, the warm sunshine of summer vacations, or the mists and snows in autumn and winter exuding a charm all their own. In any case, they are opportunities to learn about Tuscan history and culture in their most authentic aspects. Each village holds its own secrets, waiting to share them through the stories of those who will accompany you, or at the end of the excursion over a good glass of Chianti. And WeHike offers different types of experiences-discover the one that’s right for you!

chianti experience in an artisan workshop where custom wine bottle labels are made
Chianti experience in an artisan workshop where custom wine bottle labels are made

Food and wine: wine festivals, events and places in Chianti not to be missed

When Chianti is mentioned, the first association that comes to mind is with its wines, a true symbol of the area and a boast exported all over the world. Around the production of Chianti Classico (wine par excellence from the area between Florence and Siena) and Super Tuscan wines of the highest quality turns a world of companies and wineries always open to host tourists and enthusiasts, to let them taste new vintages and new products, such as the rosé wines, increasingly present on the ground.

Regarding what to do in Chianti, there is a rich calendar of appointments, starting in the spring with Vino al Vino in Panzano, I Vini del Castello in Montefioralle, Pentecost in Castellina, Radda nel Bicchiere, Cantine Aperte, I Profumi di Lamole, e Goblets of Stars in Castellina between July and August, until theGreve’s Chianti Classico Expo to close out summer, with winemakers and wine lovers from around the world. These events offer interesting wine tastings with the presence of Chianti Classico wineries to introduce the excellence of the area in a festive and welcoming environment.

On the gastronomic front, on the other hand, there are countless places to appreciate typical specialties, but one should also not miss the many festivals where one can experience a truly country atmosphere, such as the Montefioralle Rice Fritters Festival in Greve in Chianti (in March) where the Renaissance origins of Chianti’s farming tradition are celebrated.

chianti experience with visit to wineries where chianti classico is produced
Among the most fascinating things to do in Chianti we can definitely mention visiting the wineries
where Chianti classico wine is produced

The other faces of Chianti, oil, truffles and handicrafts

If we are wondering what to do in the Chianti region, we should not forget that experiences include other products and peculiarities, especially for those who enjoy the temperatures of autumn and winter. For example, the extra virgin olive oil tastings , often accompanied by walks in the olive groves, or Tuscan cooking classes, greatly appreciated by Italians and foreigners alike, to learn typical local dishes, from ribollita to peposo, occasions that can offer another flavor of Chianti culture.

Or the excursions with the truffle hunting (open year-round), to learn more about Chianti with the different varieties of truffles that reproduce naturally, or the craft workshops, which offer unique insights into traditional crafts. On the other hand, if you love the sun and heat of summer, walking along the “Blue Trails” of the Chianti River Parks and Nature Reserves allows you to cool off and relax in the wilderness.

What to do in Chianti: the ideal destination for all palates and in every season

Ultimately, Chianti is so rich in offerings, landscapes and surprises that perhaps trying to encapsulate everything in a single visit is a tall order. Better to take it easy, enjoy each moment to the fullest and experience each experience savoring its truest taste. And if you can’t accomplish everything you had in mind…. well, it means we will see each other again soon!

If you’re looking for ideas on what to do in Chianti, discover all of WeHike’s suggestions and tips for experiencing Chianti 12 months out of the year:

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