Chianti in 2 days, on foot

This 2-day self-guided walking plan for Chianti covers 13 narrated sights in an easy day-by-day order. Each day is split into a morning and an afternoon loop, and every stop has a two to three minute audio story in the Gingerguide app.

You set the pace: this is a suggested order, not a schedule. Walk it in 2 days, or stretch it out. Reorder freely; Chianti rewards a detour.

The Chianti route at a glance

• Day 1
• Day 2

Day 1

Day 1 covers 7 stops over about 30 km as the crow flies, from Volpaia to Chianti Classico Wine. ≈ 30 km between stops, straight line

Morning

1. Volpaia: Volpaia, a tiny fortified hilltop village above Radda, where a wine estate makes its wine inside the old houses, towers and churches of the medieval village. 6.1 km to the next stop
2. Badia a Coltibuono: Badia a Coltibuono, an abbey of the eleventh century in the woods above Gaiole, with a Romanesque church and bell tower, a cloister and a garden, now a wine and olive oil estate. 3.3 km to the next stop
3. Gaiole in Chianti: Gaiole in Chianti, a small market town in a green valley of southern Chianti, one of the three towns of the old Lega del Chianti and the home of L'Eroica, a ride on vintage bicycles. 6.5 km to the next stop
4. Castello di Brolio: Castello di Brolio, the castle of the Ricasoli family on a wooded hill near Gaiole, with great stone bastions, a red-brick palace of the nineteenth century, and vineyards all around. 5.2 km to the next stop

Afternoon

1. Castello di Meleto: Castello di Meleto near Gaiole, a medieval castle with round towers turned into a villa in the eighteenth century, with a tiny theatre of 1742 and a working wine estate. 5.8 km to the next stop
2. Radda in Chianti: Radda in Chianti, the old capital of the Lega del Chianti, a hill town of stone lanes with a fifteenth-century Palazzo del Podestà covered in about fifty coats of arms. 3.7 km to the next stop
3. Chianti Classico Wine: Chianti Classico, the red wine of the hills between Florence and Siena, made mainly from Sangiovese and marked with the black rooster, in a zone first defined in 1716.

Day 2

Day 2 covers 6 stops and about 1.6 km on foot, from Castellina in Chianti to San Casciano in Val di Pesa. 4 longer hops are best done by public transport or taxi. ≈ 1.6 km of walking, about 20 min

Morning

1. Castellina in Chianti: Castellina in Chianti, a hilltop town on the Chiantigiana with a fortress tower, a covered vaulted street along its walls, and a great Etruscan burial mound just outside. 8.8 km to the next stop: take transport
2. Panzano in Chianti: Panzano in Chianti, a hilltop village on the Chiantigiana with the remains of a medieval castle, looking over the Conca d'Oro, a golden bowl of vineyards, and known for its butcher shop. 4.2 km to the next stop: take transport
3. The Chiantigiana and the Black Rooster: The Chiantigiana, the winding road of about 61 km through the heart of Chianti from Florence to Siena, and the black rooster, the old emblem of Chianti and its wine. 1.6 km on foot (19 min) to the next stop

Afternoon

1. Montefioralle: Montefioralle, a tiny medieval village of stone houses on a hilltop above Greve in Chianti, built in an oval ring around its old castle and listed among the most beautiful villages of Italy. 4.5 km to the next stop: take transport
2. Badia a Passignano: Badia a Passignano, a medieval abbey of the Vallombrosan monks in a ring of cypresses above the vineyards, with a Last Supper painted by Domenico Ghirlandaio in 1476. 10 km to the next stop: take transport
3. San Casciano in Val di Pesa: San Casciano in Val di Pesa, a hill town at the northern edge of Chianti, with medieval walls, a museum of sacred art, and the nearby farm where Machiavelli wrote The Prince.

Walking distances and times follow streets and footpaths (routing by openrouteservice.org, map data © OpenStreetMap contributors). Times are walking only, at an easy pace; add time at each stop.

Updated: October 26, 2026

Full Chianti guide and all stops →