Chianti day trip from Florence or Siena
A day trip to Chianti from Florence or Siena: Greve in Chianti and its Piazza Matteotti, the hilltop village of Panzano, the Pieve of San Leolino, and Castellina in Chianti with its Rocca and covered Via delle Volte. Every stop has a typical visit length.
How long do you have?
Map: 1 days
Chianti in 1 day
Day 1
Greve in Chianti (Piazza Matteotti)
Market town of the Chianti Classico area, with a funnel-shaped arcaded square lined with wine shops, cafes and an old butcher's.
Montefioralle
A tiny walled hamlet above Greve, with a ring of stone houses, narrow lanes and vineyard views.
Historic centre of Panzano in Chianti
A short walk through the hilltop village shows its old castle walls, the church of Santa Maria and views over vineyards.
Pieve of San Leolino
Romanesque parish church on a hill just south of Panzano, with a cloister and medieval paintings, among olive groves and vines.
Historic centre of Castellina in Chianti (Via delle Volte)
A walk through Castellina follows the covered Via delle Volte inside the walls, with views and wine shops along the main street.
Rocca di Castellina
The medieval fortress in the centre of Castellina, housing the archaeological museum of Chianti and a tower with views.
Historic centre of Radda in Chianti
A small walled Chianti hill town with an oval street plan, a main square with a town hall and views over vineyards.
Watch: Chianti
A one-minute look at the plan: every stop, day by day, with the map.
Getting there
From Florence the SR222, the Chiantigiana road, reaches Greve in about 45 minutes by car; from Siena, Castellina is about 30 minutes north. Buses run from Florence to Greve and from Siena to Castellina, but linking the villages in one day is much easier by car or on an organised tour.
Staying in Florence or Siena? This day fits into those city plans, and in the Trip Builder it is one click under each of them.
When to go to Chianti
Spring and autumn are the best times, with green hills in May and the grape harvest in September and October. Summer is hot and the roads busier, while winter is quiet and some wineries and restaurants close. Greve hosts its Chianti Classico wine fair in September.
Plan the rest of your trip
- Where to stay: hotels in Chianti on Booking.com or Trip.com
- Skip-the-line tickets: museums and sights in Chianti on Tiqets
- Tours and day trips: things to do in Chianti on GetYourGuide
- Data on arrival: an eSIM for Italy from Airalo
Some of these are affiliate links: we may earn a small commission at no extra cost to you.
Tips for Chianti
- A car is the practical way to link the Chianti villages; the roads are narrow and winding, so allow more time than the distances suggest.
- Most wineries ask visitors to book tastings and tours ahead, especially at weekends and during the harvest.
- If you drive and taste wine, keep to small samples or choose a driver; Italy's drink-driving limits are strict.
- Many restaurants in the villages close between lunch and dinner, so plan the lunch stop in advance.
- Look for the black rooster seal on bottles: it marks Chianti Classico, the wine of this historic area between Florence and Siena.
Make it your own
Open the guide in Andiamo Places to see every stop on a map with walking directions, move places between days, check opening hours for your dates, and add your own finds. After the trip, your photos become a journal and, if you like, a printed photo book.
Guides are made with the help of AI and public sources such as Wikipedia, and may contain errors. Opening hours and prices change, so check before you go. Spotted a wrong photo, a pin in the wrong place, a missing stop or a better one? Write to andiamotravelapp@gmail.com: the e-mail opens with this guide filled in.
Photo credits
- Greve in Chianti (Piazza Matteotti): Velvet, CC BY-SA 3.0
- Historic centre of Castellina in Chianti (Via delle Volte): No machine-readable author provided. BetacommandBot assumed (based on copyright claims)., CC BY-SA 3.0
- Historic centre of Radda in Chianti: charley1965, CC BY-SA 2.0
- Montefioralle: Hagai Agmon-Snir حچاي اچمون-سنير חגי אגמון-שניר, CC BY-SA 4.0
- Pieve of San Leolino: Vignaccia76, CC BY-SA 3.0
Opening hours change; check before you go. Map data © OpenStreetMap contributors.
