A 7 to 10-day loop from Florence, via the Chiantigiana, Siena, the Val d'Orcia, Montepulciano, Cortona, San Gimignano, Volterra and Lucca. Short stages on hill roads, where everything happens at the gates of the historic centres: camera-controlled ZTLs, car parks outside the walls and white gravel roads.
| Days | Stop | Drive |
|---|---|---|
| Days 1 to 2 | Florence | Start |
| Day 3 | Greve in Chianti | 32 km · 35 min |
| Day 4 | Siena | 42 km · 55 min |
| Days 5 to 6 | Pienza | 88 km · 2h10 |
| Day 7 | Cortona | 48 km · 1h05 |
| Day 8 | San Gimignano | 118 km · 1h55 |
| Day 9 | Lucca | 106 km · 2h10 |
| Day 10 | Back to Florence | 75 km · 55 min |
Road route calculated from the stops (OpenStreetMap). Driving times assume no stops and no traffic: add time for photo breaks.
May-June and September-October: mild temperatures and hills still green or golden. July-August often goes above 30°C, with crowds in San Gimignano and in Siena on Palio days. In winter, the roads stay open, but winter tyres or snow chains are required from 15 November to 15 April on signed roads.
🚗 32 km · 35 min of driving from Florence
Pick up the car on the day you leave, outside the ZTL. Then the SR222, the Chiantigiana, via Strada in Chianti: hairpins between vines and olive trees.
🚗 42 km · 55 min of driving from Greve in Chianti
SR222 via Panzano and Castellina. In Siena, the ZTL is filmed 24 hours a day: use the Il Campo or Santa Caterina car parks.
🚗 88 km · 2h10 of driving from Siena
Via Cassia (SS2) to Buonconvento, SP45 towards Montalcino, Sant'Antimo, then Bagno Vignoni. Alternative: SP438 via Asciano and the Crete Senesi.
🚗 48 km · 1h05 of driving from Pienza
SS146 via Montepulciano, then the plain of the Val di Chiana. Final climb up hairpins; ZTL at the top, car parks below the ramparts.
🚗 118 km · 1h55 of driving from Cortona
Toll-free expressways Perugia-Bettolle, Siena-Bettolle and the Siena ring road, then the RA3 to Monteriggioni and Colle di Val d'Elsa.
🚗 106 km · 2h10 of driving from San Gimignano
SS68 to Volterra, then the SS439 Sarzanese through the Era valley. Lucca: ZTL 24 hours a day, car parks outside the walls.
🚗 75 km · 55 min of driving from Lucca
Keep Florence (2 nights), Siena via the Chiantigiana (2) and Pienza (2), then head back to Florence via San Gimignano. Cortona, Volterra and Lucca are dropped.
| All categories, September (most expensive month) | ≈ €52 a day |
|---|---|
| All categories, November | ≈ €23 a day |
| Small car, Florence, average | ≈ €38 a day (Kayak, Sept. 2026) |
| Small car, Pisa airport, average | ≈ €26 a day |
| Vehicle | Small car: narrow lanes, tight car parks, hilltop towns and white gravel roads. Book an automatic early. |
|---|---|
| Where to pick it up | On the day you leave Florence, at the airport. Pisa is cheaper: in that case, start the loop with Lucca. |
| Insurance | CDW and theft cover compulsory: $24 to $55 a day at the counter, excess of $125 to $1,180. |
| Bank card | Few cards have car hire insurance that covers Italy: check before declining the excess waiver. |
| Age and card | Rarely under 21, young driver surcharge under 25 or 26. Credit card in the driver's name. |
| Fines | The rental company gives your details to the police, who have 360 days to notify you of the fine. |
⚠️ Every ZTL has its cameras: Florence, Siena, Lucca, Montepulciano, Volterra, Cortona. Each entry costs €83 to €332, plus the rental company's fees.
Any European Union licence is enough, with no International Driving Permit. Other licences: check whether an International Driving Permit is required.
As in mainland Europe. Dipped headlights compulsory outside built-up areas, even by day.
50 in towns. In the rain: 110 and 90. Licence held for less than 3 years: 100 on motorways, 90 on expressways.
Zero under 21 and with less than 3 years' licence. Over the limit: €543 to €2,170.
Centres filmed, "Varco attivo" sign. One fine per day and per ZTL, 30% less if paid within 5 days.
Plus summer nights from Thursday to Saturday, from April to early October.
Florence and Siena: the hotel registers your number plate. Lucca: a direct trip is tolerated. Cortona: no exemption.
Dirt tracks to farms, estates and chapels. Drive slowly, avoid them after a storm, dust guaranteed in summer.
Expressway with no toll and no hard shoulder; 60 km/h on dangerous bends.
For holding a phone while driving, with a possible licence suspension.
Winter tyres or chains on board on roads where an ordinance requires them.
≈ €2.14 a litre for petrol, €2.28 for diesel (21 September 2026)
Price recorded in September 2026: it changes every week, sometimes by 10 to 20 cents in a month. Today's price: Osservaprezzi carburanti (Italian ministry) →
⛽ 509 km at 7 l per 100 km: about €80 at September 2026 prices, to share between passengers.
Weekly national average from the Italian Ministry of Energy, rising since August. More expensive on motorways: fill up in the towns.
| A11 Florence-Pisa Nord (Lucca-Florence slightly less) | €7.10 by car |
|---|---|
| RA3 Florence-Siena, Siena-Bettolle, RA6 | Free |
| Villa Costanza car park (Florence, on the A1) | €7 for 24 hours, €20 a week, T1 tram |
| Parterre car park (Florence) | €2 an hour, €15 a day |
| Il Campo, Duomo, San Francesco, Santa Caterina car parks (Siena) | €2 an hour, €35 a day, €25 hotel rate |
| San Gimignano, P1 Giubileo | €2 an hour, €7 a day |
| San Gimignano, P2 Montemaggio | €3 for the first hour, €15 a day |
| Florence ZTL, daytime | Monday-Friday 07:30-20:00, Saturday 07:30-16:00 |
|---|---|
| Florence ZTL, summer nights 2026 (from 23:00 on Thursday, 20:00 on Friday, 16:00 on Saturday) | 2 April-4 October, until 03:00 |
| Siena and Lucca ZTL | 24 hours a day, all year round |
| Montepulciano ZTL | 24 hours a day from May to September, daytime otherwise |
| Volterra ZTL | 10:00-19:00, 21 March-1 November; 10:00-17:30 in winter |
| Palio di Siena | 2 July and 16 August: centre closed off, car parks packed |
| L'Eroica, Gaiole in Chianti | 3-4 October 2026: the Chianti white roads overrun by cyclists |
| Roads under a winter ordinance | Winter tyres or chains from 15 November to 15 April |
Allow 7 to 10 days. Our loop covers 9 nights over 7 stages: Florence, Chianti, Siena, the Val d'Orcia, Cortona via Montepulciano, San Gimignano, then Lucca via Volterra. Drives stay short, rarely more than two hours. In 7 days, keep Florence, Siena and Pienza, with San Gimignano on the way back.
Never drive past a ZTL sign marked "Varco attivo". Park outside the walls: Villa Costanza or Parterre in Florence, Il Campo or Santa Caterina in Siena, P1 or P2 in San Gimignano. If your hotel is inside a ZTL, ask it to register your number plate. Each offence costs €83 to €332, plus the rental company's fees, and can be notified up to a year later.
For 10 days in September, allow about €520 for car hire (€52 a day, Kayak average), less from Pisa. Add petrol at €2.14 a litre (September 2026), a single toll (€7.10 at most on the A11) and €7 to €35 a day for parking in towns. In November, car hire drops to around €23 a day.
Yes: these white roads, of gravel or dirt, are public and passable in an ordinary car in dry weather. They serve the farms, estates and hamlets of Chianti, the Crete Senesi and the Val d'Orcia. Drive slowly, avoid them after a storm and check that your excess waiver covers tyres and the underbody.
Outside the ZTL. Villa Costanza, reached from the A1: €7 for 24 hours, €20 a week, T1 tram to Santa Maria Novella station in 22 minutes. Parterre, north of the centre: €2 an hour, €15 a day. The simplest option is to see Florence on foot and pick up the car on the day you leave.
Not with an EU licence: any European Union licence is enough. Other licences: check whether an International Driving Permit is required. Rental companies often ask for a minimum age of 21, a surcharge under 25 or 26 and a credit card in the driver's name. With a licence held for less than 3 years: zero alcohol, 100 km/h on motorways and 90 on expressways.
Driving rules, prices and closures checked in September 2026; hotels checked on OpenStreetMap and then on Booking. Rules change: read the official source before you leave, and check your own government's travel advice for the country. Stop photos: Wikimedia Commons, authors and licences under each image.
Off We Gooo road trip guide · offwegooo.com/en/road-trips/tuscany · by Pierrick, updated 1 October 2026
