Renaissance art, Chianti vines & cypress roads
This is leg 2 of 3.
Travel leg · Tuscany Hill Towns
Chianti to Siena
Chianti and Siena sit about 29 km (18 mi) apart in a straight line, with Siena to the south. It is leg 2 of 3 on our Tuscany Hill Towns itinerary, a 7-day trip. Here is how long it takes by car, what to see on the way and where it fits in a real itinerary.
- Straight-line distance
- 29 km · 18 mi
- Est. road distance
- 35–41 km
- Est. drive time
- 25–50 min
- Direction
- Heading south
- Curated routes
- 1 itinerary
Road distance is estimated as 1.2–1.4× the straight line; drive time assumes average speeds of 50–80 km/h with no stops or traffic. These are rough estimates — check a maps app for the actual route.
Ways to get there
We don't have live routing data, so the figures below are labelled estimates built from the straight-line distance. Use them to plan the day, then confirm in a maps app.
By car
Most travelers on our Tuscany Hill Towns itinerary do this leg by car. We estimate 35–41 km (22–26 mi) of road and 25–50 min behind the wheel, so check live traffic before you set off.
By train
Our Tuscany Hill Towns guide also mentions trains for parts of the trip. Whether a direct train links Chianti and Siena depends on the line — check timetables.
Rail or a short ride connects Florence and Siena, but the countryside rewards a rental car. Chianti and the Val d'Orcia are made of small roads and villages, so driving gives you freedom. Pick a designated driver if wine tastings are planned.
Worth stopping for
Picks from our curated guides at both ends.
When you arrive in Siena
Stay one night to see the Campo after day-trippers leave; one full day covers the cathedral and museums.
Piazza del Campo
Shell-shaped square where the Palio horse race runs in July and August.
Torre del Mangia
Tall tower above Palazzo Pubblico with views of Siena's rooftops.
Pasticceria Nannini
Siena's classic café for espresso, ricciarelli and panforte.
Antica Drogheria Manganelli
Grocery since 1879 selling panforte, local wine and oils.
Osteria Le Logge
Old pharmacy turned restaurant serving refined Tuscan food.
Museo Civico
Palazzo Pubblico's frescoed halls, including Lorenzetti's Good and Bad Government.
Before you leave Chianti
Spend 1–2 days driving the SR222 between Greve, Panzano and Radda, with winery visits booked ahead.
On this curated route
Where Chianti → Siena sits in the full itinerary. Highlighted stops are this leg.
Going the other way? Siena to Chianti is the same 29 km in a straight line, heading north. Reverse directions in Google Maps ↗
Chianti to Siena: questions travelers ask
How far is Chianti from Siena?
Chianti is about 29 km (18 mi) from Siena in a straight line, with Siena to the south. By road, we estimate 35–41 km (22–26 mi), or 1.2–1.4 times the straight line. Check a maps app for the exact route.
How long does it take to drive from Chianti to Siena?
An estimated 25–50 min, assuming 35–41 km of road at average speeds of 50–80 km/h with no stops or traffic. It is not a routed time, so check a maps app on the day.
Which itineraries include the trip from Chianti to Siena?
Our Tuscany Hill Towns itinerary includes this leg. Tuscany Hill Towns runs about 7 days across 4 stops, best in Apr – Jun, Sep – Oct.
Onward from Siena
- Siena to Val d'Orcia 39 km
Getting to Chianti
- Florence to Chianti 21 km
Guides for both ends
- Chianti travel guide
- Chianti weather best time to visit
- Siena travel guide
- Siena weather best time to visit
Siena by month
Plan Chianti → Siena with your crew
Add this leg to a shared itinerary, poll the group on where to stop, split fuel and tickets, and keep everyone's packing list in one place in TripsCircle.