Siena to Chianti: Wineries and Hill Towns

Visit Siena Guide editorial·May 19, 2026·6 min read

Chianti starts at Siena's northern edge. The famous wine region stretches up toward Florence with hill towns, castles, and cellars in between.

# Siena to Chianti: Wineries and Hill Towns

Chianti starts at Siena's northern edge. The famous wine region stretches up toward Florence with hill towns, castles, and cellars in between.

Key facts

By car: essential. Public transport is poor in the Chianti area.
Day-trip loop: Castellina in Chianti, Radda in Chianti, Gaiole in Chianti — all under 30 min from Siena.
Winery visits: book 1-2 days ahead. Tastings run 15-40 euro per person.
Best for: scenic driving, lunch in a castle, 2-3 winery stops.
Group tours from Siena: 80-150 euro per person, including transport, lunch, 2 wineries.

What I tell visitors

If you don't drive, take a small-group Chianti tour from Siena. The roads are too narrow and twisty for everyone to be enjoyable behind the wheel.

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Final word

Whatever brings you to Siena — food, the Palio, the Tuscan countryside — slow down. The city repays attention. If you have a tip to add or a correction, write us at redazione@visitsienaguide.it.