
Living in Tuscany, like a local Chiantishire, means immersing yourself with your gaze among hills covered in golden grapes, strolling slowly through small villages, and experiencing fantastic culinary and wine adventures. In this article, we therefore suggest 10 different things to do, original and very enjoyable, to make you feel part of this land from the very beginning.
Find out what to do in Chianti
10 stop Walking in the vineyards at dawn

If you want to experience something unique, like a local Chiantishire, don't miss the opportunity to take a walk among the vineyards in the early hours of the morning. Just ask permission from a small wine producer. Imagine being there early in the morning, the air is fresh, crisp, and the soft light of the rising sun caresses everything. Breathe in the scent of the countryside, listen to the birds singing, and closely observe the grape berries that are slowly ripening. Don't you find all this wonderful? It's a perfect moment.
9 stop Participate in the grape harvest like a local Chiantishire

Living like a local Chiantishire also means discovering the most authentic side of agricultural tradition: the grape harvest. Between September and October, the hills with villages like Greve in Chianti, Radda, etc., come alive with voices and baskets full of grapes, in a ritual that brings together families, farmers, and enthusiasts. Participating in this experience is not just about collecting ripe bunches, but also about sharing moments of togetherness, listening to stories related to wine, and understanding the effort behind every bottle of Chianti Classico. For you, participating in the harvest is an unforgettable opportunity, a chance to feel part of a community that celebrates wine as art and tradition.
Discover Chianti with a Wine Tour8 stop To collect the olives like a local Chiantishire

If you want to live like a local Chiantishire, you cannot miss the magic of the olive harvest and the tasting of the new oil. Between October and November, the olive groves are full of nets, ladders, and people, collecting mature olives that are then taken to the mills for pressing. The residents of Chianti love to enjoy it warm on toasted bread. Participating in the harvest or a tasting of new oil will help you discover how precious this green gold is and why every family in Chianti considers it a true treasure. It is an authentic experience not to be missed.
7 stop Going to the weekly market in Greve or Panzano

One of the best ways to live like a local Chiantishire is to visit the weekly markets in Greve or Panzano in the morning. Here you will find stalls rich with fresh and genuine products: typical cheeses, Tuscan cured meats, freshly baked bread, seasonal vegetables, and, of course, local wine. Strolling among the stalls is an authentic experience that allows you to observe the daily life of the inhabitants, chat with the producers, and perhaps taste some specialties on the spot.
6 stop Try the farmer's snack

Savoring a rustic snack like a local Chiantishire means eating in the simple and genuine way of Tuscan farmers. Rustic bread, topped with a drizzle of freshly pressed extra virgin olive oil accompanied by homemade cured meats and cheeses. This is not just a snack, but a ritual, sharing food as the farmers did after working in the fields. Enjoying such a snack allows you to appreciate authentic flavors that have belonged to this land for centuries.
5 stop Discover the hidden Romanesque parishes

Visiting the ancient pievi like a local Chiantishire is a way to discover hidden artistic and spiritual aspects of the Tuscan countryside. Scattered among hills and vineyards, these small Romanesque churches hold centuries of history. Many are located in small villages or along country roads, away from tourist circuits, and provide an atmosphere of silence and reflection. Entering a pieve means taking a leap into the past: admiring simple architectures, ancient stones, and details that tell the faith and life of rural communities. Beautiful!
4 stop Taking a bike ride through white roads and cypress tree

Cycling along the roads, between rows of cypress trees and rolling hills, is an experience that allows you to live like a local Chiantishire. By bike, you can discover hidden corners, breathe the clean air of the countryside, and enjoy the scenery. The dirt roads typical of this region will take you through vineyards, medieval villages, and unspoiled landscapes, offering you a direct connection with nature.
3 Stop Learning to cook typical dishes with local grandmothers

Learning to cook typical dishes together with the local grandmothers is one of the most fun ways to live like a true Chiantigiano. Home lessons on ribollita or pici are definitely much more engaging than cooking classes for tourists. Learning to make pasta or soups is a beautiful experience that brings you into the heart of everyday life in Chianti. Finally, sharing the lunch prepared together makes food a bridge between cultures and stories.
Join a Cooking Class in Chiantishire2 stop Savouring vinsanto in the small family wineries.

Another experience we suggest you have like a local Chiantishire is to taste vinsanto in small family wineries. This sweet wine is often accompanied by cantucci, the typical Tuscan biscuits to dip. In family-run businesses, you can listen to the farmer's stories and discover the secret of aging of the vinsanto in caratelli, passed down from generation to generation.
1 stop Participating in village festivals

Finally, participating in village festivals, is one of the most traditional ways to live like a local Chiantishire. During the year, the small towns in this area organize festivals dedicated to wine, new oil, Florentine steak, wild boar, or seasonal products. Join in the folk dances in the square and visit the food stalls to taste typical dishes prepared by local families. These events are not just meant for tourists, but represent moments of gathering for the community.
About the author
Written on 10/09/2025
Giacinta Navarra
Dive into the heart of Chiantishire and discover 10 things to do like a local to experience something new, off the beaten path.