Short “getaways,” often on weekends, are true mini-vacations. How to fully experience the magic of Chianti, a small paradise in the heart of Tuscany, in just 2 days? Here are some suggestions for fully enjoying a weekend in Chianti.

From Greve in Chianti to Panzano in Chianti
The starting point for this first itinerary for a weekend in Chianti is Greve in Chianti, the most populous village in the Chianti area, which developed in the Middle Ages as a mercatale and therefore lacked fortifications.
The beautiful Piazza Matteotti-with the statue of Giovanni da Verrazzano in the center-is the hub of the town: every Saturday it still hosts the centuries-old tradition of the market, while in the loggias a stop at the Macelleria Falorni, a historic retailer of excellent cured meats accompanied by a good glass of Chianti wine, and Antonella Ciapetti’s ceramics store, which has been creating unique and wonderful pieces with her own hands for more than 30 years, is a must.
From the center of Greve in Chianti, there are many options to continue: in fact, nearby is the village of Montefioralle, reviewed as the Borgo più Bello d’Italia 2022(read the article in Il Sole 24 Ore) for its architectural excellence and the authenticity of the place, with which to associate a visit to the cellars of one of the many wine producers along the way.
A short distance away stands another jewel, the Monastery of the Badia di Passignano, still inhabited by monks of the Vallombrosian order, guardians of its cultural and historical treasures.
At the end of the first day of your weekend in Chianti, don’t miss the ancient village of Panzano in Chianti, on top of a hill from which there is a spectacular view of the Conca d’Oro, an ancient valley rich in history and today very vocated for the production of Sangiovese.
You can stop to sample the delicacies of Dario Cecchini, Chianti’s most famous butcher, and, just outside Panzano, visit the Pieve di San Leolino, with a three-aisled interior, a charming cloister and a wonderful view of the Chianti countryside.

Barberino Val d’Elsa to Castellina in Chianti
A location in Chianti that is still little known but worth visiting is Semifonte, visible as early as Barberino Val d’Elsa. This is where the second itinerary of your Chianti weekend begins.
Semifonte is an enchanted place rich in history: visit the Chapel of St. Michael the Archangel near Petrognano, an evocative religious building topped by a dome that reproduces on a small scale (1:8) the one built by Filippo Brunelleschi for Florence Cathedral.
On the gastronomic theme, one of the must-do stops is a cheese tasting at the Trapanotto Farm, a few miles away.
A half-hour drive away, you then reach the village of Castellina in Chianti, formerly inhabited by the Etruscans, as evidenced by the coeval Montecalvario tumulus. When you reach the historic center of the village, walk along Via delle Volte, an evocative covered walkway, created by Brunelleschi, that runs under the supporting arches of the palaces facing the main street with openings to the gentle panorama of the Chianti hills.
Every year, during Pentecost in Castellina in Chianti, this street hosts tastings of local wines in the company of producers. Also tied to local tradition are the dishes that, along with a good glass of Chianti wine, you’ll find at the nearby Macelleria Stiaccini.
Finally, near Castellina is the village of Fonterutoli, once on the border between the states of Florence and Siena(learn more about the Legend of the Black Rooster), where in addition to strolling through the streets, the renowned winery of the same name awaits you.

Discover Chianti with an organized weekend: hiking, good food and expert guides
Do you want to have a unique experience in Chianti with a close-knit group and an experienced guide? Participate in the Food and Wine Hiking Weekend organized by WeHike! With us, you will explore historic villages, admire breathtaking landscapes, and enjoy dinners and tastings at iconic places like Dario Cecchini’s butcher shop. Join this guided adventure into the heart of Chianti and discover a different way to explore this magnificent land. Discover the perfect adventure for your weekend in Chianti
If you prefer more specific experiences, explore all our offerings that combine hiking, tastings, workshops, crafts and more here.