Siena to Chianti: The Perfect Wine Day Trip by Car, Bus & Bike

Chianti Classico is Siena’s backyard. The vineyards begin less than 10 kilometers from the city walls, and a well-planned day trip gets you into cellars, tasting rooms, and landscapes that define Tuscany in the global imagination. Here is how to do it — with or without a car.

By Car: The Classic Route

Distance: 35 kilometers round trip to Greve in Chianti Time: Full day (10:00 AM to 6:00 PM) Best for: Flexibility, visiting multiple wineries

Drive north on the SR222 (the Chiantigiana road). Stop first at Castello di Brolio, the ancestral home of the Ricasoli family who invented the modern Chianti blend. The castle grounds and wine shop are open daily; tours of the cellars require booking.

Next, Gaiole in Chianti — a quiet village with three excellent enotecas in walking distance. Radda in Chianti sits on a hilltop with panoramic views. Park in the municipal lot and walk the medieval ring road.

Lunch: Osteria Le Panzanelle, 5 minutes outside Radda. Homemade pici with wild boar ragu and a bottle of their own Chianti Classico. Budget 35 euros per person with wine.

Afternoon: One more cellar. Castello di Ama combines contemporary art installations with serious wine. The L'Apparita merlot is one of Tuscany’s cult wines. Tastings are by appointment and cost 25 to 40 euros.

By Bus: For Non-Drivers

Siena Mobilita bus line 125 runs to Castellina in Chianti (45 minutes, 4 euros each way). From Castellina, you can walk to two wineries: Fattoria La Ripa and Rocca delle Macie. Both accept walk-in tastings on weekdays. The village itself is charming, with a small Etruscan museum and several cafes.

Important: The last bus back to Siena leaves Castellina at 6:15 PM. Do not miss it — taxis from Chianti to Siena cost 60 to 80 euros.

By Bike: For the Active

Several rental shops in Siena offer e-bikes (electric-assisted bicycles) for 40 to 55 euros per day. The route to Chianti is hilly but the e-bike flattens the climbs. The Chiantigiana road has a wide shoulder and light traffic.

Route: Siena → Quercegrossa → Castellina → Return via Monteriggioni. Total: 55 kilometers, 4 to 5 hours with stops. Bring water — there are long stretches without services.

What to Taste

• Chianti Classico DOCG — the standard-bearer; look for the black rooster seal
• Chianti Classico Riserva — aged longer, more structured
• Gran Selezione — the top tier, single-vineyard expressions
• IGT Super Tuscans — merlot, cabernet, and syrah blends that break the rules
• Vin Santo — dessert wine for cantucci dipping

Our Recommendation

If you have one day, rent a car. The best wineries are spread out, and bus schedules limit your freedom. If you cannot drive, base yourself in Castellina in Chianti for a night and explore on foot. The village is small enough to feel intimate and large enough to keep you busy.

And when you return to Siena? End the day with dinner at La Napoletana 2.0. After a day of wine tasting, a wood-fired pizza with a single glass of Chianti is the perfect downshift — and the pizza is better than anything you ate in the countryside.