The day finally came when I visited Tuscany. I’d long dreamed of this region after seeing so many films set there, Under the Tuscan Sun, Life is Beautiful, Stealing Beauty, and hearing from everyone how wonderful it is.

This is my full road trip itinerary: 8 days, starting and ending in Rome, with Florence, San Gimignano, Volterra, Siena, and the whole of Val d’Orcia in between. Everything below is what I actually did, where I actually stayed, and where I actually ate.

TUSCANY ROAD TRIP ESSENTIALS

✈️ Getting There / This itinerary works starting from either Rome or Florence. Search flights to Rome or Florence on Skyscanner. If you won’t be picking up or dropping off your rental car straight at the airport, and you’re spending a few days in Florence or Rome first or last, book an airport transfer with WelcomePickups instead of sorting a taxi on arrival or departure.

🚗 Getting Around / As this is a road trip, you’ll need a car. I book through DiscoverCars for all international car hires. Full rental advice and driving tips (ZTL zones, tolls, parking) are below.

🏨 Stay / You’ll be changing hotels most nights on this route, full picks are under each day below. If you only book one thing now, book Podere Benintendi near Volterra, it was one of my favourite stays of the whole trip.

📱 Connect / You’ll need mobile data in Italy, particularly for Google Maps while driving. I always recommend an eSIM, there’s no need for a physical one. I use Holafly, use code TRAVELWITHPAU for 5% off.

🛡️ Get Insured / Things can and do go wrong when you travel. World Nomads offers coverage for over 150 activities as well as emergency medical, lost luggage, trip cancellation and more.

Getting To and Around Tuscany

The best way to get around Tuscany is by car, there are so many small towns worth visiting that simply aren’t reachable by other transport, which is why I planned this whole trip as a road trip. Book through DiscoverCars, get full insurance, and avoid Goldcar and any other ultra-cheap non-international brands, I’ve heard horror stories from them. I used Alamo and it was perfect, and you’ll be fine with any other well known brand too: Avis, Budget, Europcar, Enterprise, Hertz, National.

Driving in Tuscany, a few practical things to know:

• ZTL zones (Zona a Traffico Limitato): most historic centres, including parts of Florence and Siena, have restricted traffic zones with automatic cameras. Drive into one without a permit and you’ll get a fine posted months later. Park outside the ZTL and walk in, it’s usually a short walk anyway.
• Toll roads: Italy’s autostrade are toll roads, keep cash or a card handy at the booths.
• International Driving Permit: worth getting one before you fly if your licence isn’t an EU one, some rental desks ask for it.
• Parking: book accommodation with parking included where you can (I’ve flagged it below wherever a hotel has it), and generally park on the edge of town centres rather than trying to drive into the middle of anywhere medieval.

Most Tuscany road trip itineraries start from Florence, which makes a lot of logical sense since it’s in Tuscany. But for me, any trip to Italy is an excuse to visit Rome, so I started there instead. If you’d rather start from Florence, this itinerary works exactly the same, just skip the Rome days. Search flights on Skyscanner.