The itinerary at a glance
| Day | Stops | Route (approx.) | Overnight |
|---|---|---|---|
| 1 | Rome → Orvieto → Montepulciano | 120 km to Orvieto, then 90 km | Montepulciano or Pienza |
| 2 | Pienza, Bagno Vignoni, San Quirico d'Orcia (Val d'Orcia) | 30 to 50 km on small roads | Pienza or Montalcino |
| 3 | Val d'Orcia → Siena | 55 to 60 km | Siena |
| 4 | Siena → Chianti road → Florence | 70 km on the scenic road | Florence |
| 5 (optional) | San Gimignano from Siena or Florence | 40 km from Siena | depends on your flight |
Rome is about 280 km from Florence by motorway, close to three hours without stops; the whole point of a road trip is not to drive it in one go.
Before you leave: renting the car
For a road trip, pick the car up at Fiumicino or Ciampino airport, never in central Rome: you avoid the ZTL and drive straight onto the motorway. Our guide to car rental at Fiumicino covers the rental companies, the deposit, insurance and the ZTL trap. To compare offers, see the cars available in Rome on Booking Cars or at Fiumicino airport.
- One-way rental: returning the car in Florence after picking it up in Rome usually adds a one-way fee. Compare it with the cost of a round trip: the amount varies by company and date.
- Size: a small car is enough for two and fits village streets better; an automatic costs more and should be booked early.
- Licence: bring your driving licence; depending on your country, an international driving permit may be required, so check with the rental company before booking.
Day 1: Rome, Orvieto and Montepulciano
Leave Rome early on the A1 motorway heading north. Orvieto, about 120 km away (allow 1 h 15 to 1 h 30), sits on a tuff plateau; its mosaic-covered cathedral is worth a stop of two to three hours. Our page on Orvieto has the details. Park at the car park at the foot of the town and take the funicular up: the old town is largely pedestrian, and it is your first ZTL test of the trip.
In the afternoon, continue to Montepulciano, about 90 km away (1 h 15 to 1 h 30), a village perched on a ridge and known for its Vino Nobile wine. Park outside the walls: the centre has restricted traffic, and the main street is steep and best done on foot. Have dinner and stay the night here, or carry on to Pienza (about 15 km) if you prefer somewhere quieter.
Day 2: the Val d'Orcia
This is the most beautiful stretch of the trip, and where a car is truly irreplaceable. The rolling hills, lines of cypress trees and isolated farmhouses of this UNESCO-listed valley are best discovered on small roads, without hurry.
- Pienza: a small Renaissance town laid out in the 15th century, famous for its pecorino cheese. It takes an hour or two; park outside the walls.
- Bagno Vignoni: a village built around a large thermal-water pool in the village square. Swimming in the pool is not allowed: you look at it, then find a spa nearby.
- San Quirico d'Orcia: its medieval centre and Renaissance gardens can be seen quickly.
- Montalcino (optional): about 40 km from Pienza, the town of Brunello, for a winery tasting. If you taste wine, nominate a driver: alcohol checks are frequent and penalties severe.
Allow a full day: distances are short, but roads are slow and you will stop constantly for photos.
Day 3: on to Siena
From the Val d'Orcia, Siena is 55 to 60 km away (about an hour). Take the Crete Senesi, a landscape of pale clay hills, if you have time. Do not drive into the centre of Siena: the ZTL is strictly monitored. Leave the car in a car park on the edge of town or near the station and walk up to the Piazza del Campo. For what to see (Piazza del Campo, Palazzo Pubblico, cathedral), see our guide to Siena and San Gimignano from Rome, which also covers visits.
Spend the night in Siena: you get the square to yourself in the evening, after the day-trip groups have left.
Day 4: the Chianti road to Florence
From Siena to Florence, take the SR 222, the Chiantigiana, rather than the fast road: about 70 km and a good two hours with stops, among vineyards and villages such as Castellina, Radda or Greve in Chianti. Book a tasting in advance if you want one, and again, only one driver drinks. If the fast road is enough for you, allow about an hour.
Before reaching Florence, do not drive into the centre: the Florence ZTL is watched by cameras and fines are sent to the rental company, which passes them on with an admin fee. Return the car on the outskirts, at Florence airport or at an office near the station, and enter the city on foot, by tram or by taxi. Our guide to Florence from Rome describes what to see in a day.
Day 5 (optional): San Gimignano
From Siena, San Gimignano is about 40 km away, 45 minutes to an hour by road: a half-day trip. Car parks are outside the walls, since the centre has restricted traffic. The village and its towers take one to two hours; the full programme is in our guide to Siena and San Gimignano from Rome.
ZTL, parking and tolls: the traps of driving
- ZTL: almost every town on this itinerary (Orvieto, Pienza, Montepulciano, Siena, San Gimignano, Florence) has a historic centre with restricted traffic. A round sign with a red circle and the words "ZTL" or "varco attivo" means the cameras are running. See also our guide Driving in Rome: ZTL, parking and rental for fines and how the system works.
- Parking: use car parks outside the walls, pay at the meter or with the app, and expect several euros an hour in the most touristy towns. Rates change: check at the entrance.
- Tolls: motorways (A1) are toll roads; take the ticket on entry and pay on exit by card or cash.
- Hotels: if your accommodation is inside a ZTL, ask whether it can register your plate with the town hall, and where to park.
- Fuel: self-service pumps are cheaper than attended ones; in rural areas they close early and on Sundays.
When to go
Spring (April to June) and early autumn (September-October) are the best times: the hills are green or golden, temperatures are pleasant, and the roads are less crowded than in midsummer. In July and August it is very hot and villages are full; in winter, some country roads are muddy and many places close.
If you have an accident
On the spot: get to safety, switch on the hazard lights, check for injuries and call emergency services (112 (emergencies), 113 (police), 118 (ambulance)). Fill in the European accident statement with the other driver; call the police if anyone is hurt, if you disagree, if the other driver leaves, or if your rental contract requires it. Photograph the vehicles, the plate, the road and the damage, note the other driver's details, and call the rental company before any repair.
Who pays what: damage to the car is covered by the rental company's protection (CDW), subject to its excess (deductible), or by an excess cover bought with the rental; injuries and medical costs fall under your travel insurance. Travel insurance does not pay for the rental car or for damage to third parties.
SafetyWing covers medical costs after an accident abroad; check the policy's conditions for driving (a licence valid in the country, a helmet on a scooter).
Without a car: the alternative
If you would rather not drive, do Orvieto by train from Rome, Florence by high-speed train (see Florence from Rome) and Siena on an organised tour. You will miss the Val d'Orcia: that is the price. For more day-trip ideas, see our day trips from Rome; if you are torn between the two cities, our comparison Rome or Florence helps.
