Tuscany: 7 Day Road Trip Itinerary

Italy

A Florence loop through Chianti, Siena and Val d’Orcia, balancing village squares, country views and long lunch breaks.

Suggested season: April–June / September–October

Driving estimates exclude stops, traffic and ferry waits. Pins represent town/area centres; use the daily map links for navigation.

Day 1: Florence

Walk around the Duomo and Arno. Choose one museum and consider collecting the car after your city visit.

0–0.5 hours driving · Overnight: Florence

Google Maps

Day 2: Florence → Greve in Chianti → Siena

Pause for coffee in Greve’s square, then take country roads to Siena. Park outside the walls and spend the evening in the centre.

2–3 hours driving · Overnight: Siena

Google Maps

Day 3: Siena → San Gimignano → Siena

Spend half a day among San Gimignano’s towers and lanes. Relax around Piazza del Campo after returning to Siena.

1.5–2.5 hours driving · Overnight: Siena

Google Maps

Day 4: Siena → Pienza

Use designated viewpoints on the way into Val d’Orcia. Explore Pienza’s lanes, cheese shops and valley terraces.

1–2 hours driving · Overnight: Pienza

Google Maps

Day 5: Pienza → Montepulciano → Pienza

Walk Montepulciano’s hilly historic centre. Return to Pienza for a short countryside walk in the afternoon.

1–1.5 hours driving · Overnight: Pienza

Google Maps

Day 6: Pienza → Montalcino

Explore Montalcino’s fortress area and streets. Add Sant’Antimo if its opening hours fit your day.

1–1.5 hours driving · Overnight: Montalcino

Google Maps

Day 7: Montalcino → Florence

Choose one short stop on the way to Florence. Return the car without entering a restricted ZTL zone.

2–3 hours driving · Overnight: End of itinerary

Google Maps

Before you drive

Watch for ZTL restrictions in historic centres and walk from outer car parks. Arrange a non-drinking driver or transfer for wine tasting.

Official destination information

Estimated budget for two

Illustrative October 2026 planning allowances, not live prices or quotes. Two adults, one rental car, a shared mid-range room and 6 nights. Flights, visas, insurance upgrades, deposits and one-way rental fees excluded. Peak season and major activities may exceed these amounts.

Room per night: 100–180 EUR
Car per day: 40–75 EUR
Food for two per day: 55–95 EUR
Fuel for the trip: 90–150 EUR
Visits, parking and toll allowance: 80–180 EUR

Total range including 10% reserve: 1579–2860 EUR

Midpoint estimate / per person: 2223 / 1111.5 EUR

Hours, fees and access may change; check official links before travelling.