You’ve seen all the big tourist sites, you’ve enjoyed a walking tour with an expert local guide, and maybe you’ve even hopped on a train to enjoy some day trips around the gorgeous Tuscan countryside. But after all this, you still feel like you’re missing something during your visit to Tuscany. If you’re one of those people pining for authentic experiences and to see the “real” side of central Italy, then you should consider going on a Tuscany road trip.
Planning a road trip can be daunting in your own country, let alone in a foreign one! Worry not, because in this guide we’ve gathered everything you need to know to plan the ultimate road trip in Tuscany. So keep reading for the why, the how, and the what to see and do for the ultimate Tuscan road trip.
Why you should take a road trip in Tuscany
With its rolling terrain and dozens of tiny villages built into mountains or on hilltops, there are just some places you can’t get to in Tuscany unless you have a car. That’s why a road trip to Tuscany is the best way to explore Italy’s most popular region like a local.
When you travel to Tuscany by car, you get the flexibility of when you want to leave, and how long you stay in any given place. If you opt for a bus tour, you’re at the mercy of all the other guests, the guide, and even the driver. Plus, you can cut your travel time down by several hours when you take your own car, giving you more time for sightseeing and eating!
Top towns to visit on a Tuscan road trip
While the robust public transport system can get you to most places in Tuscany, there are some villages and towns in Tuscany that are best accessed by car. For the best experience, we always recommend finding one town you want to visit, then driving around the surrounding roads and allowing attractions to grab your attention. But if you prefer to plan out your journey, consider stopping through these towns.
Panzano in Chianti
This beautiful town lies in the heart of the Chianti Classico wine region, so it’s a great place to stop for lunch in between winery visits. Panzano is home to the butcher shop and restaurants of Dario Cecchini, an eighth-generation butcher renowned in his own right and made famous by the Netflix show Chef’s Table.
If a meat-tasting menu isn’t your thing, then we recommended having lunch outdoors with a sweeping view of the Chianti hills at Ristorante Oltre il Giardino.
Speaking of wineries, the tour and tasting experience is unmatched at Gagliole. With a commitment to biodiversity in the vineyard and organic winemaking, the wines you’ll taste here are out of this world and good for the planet! Gagliole also has the luxury bed and breakfast La Valletta, where you can stay in an apartment in a renovated villa.
Il Borro
Il Borro is the ultimate hidden gem in Tuscany. It’s a tiny, ancient hamlet surrounded by over 2,500 acres of organic farmland and vineyards, with a luxury resort and spa. The area belonged to a duke, then in the 1990s the Ferragamo family bought the hamlet and revived it into the truly unique ecosystem it is today.
You can stay at Il Borro for a relaxing getaway under the Tuscan sun, or just stop by for lunch at the gourmet farm-to-table restaurant overlooking the pool, surrounding hillsides, and forest. Then, wander around the village and pop in to see artisans at work.
Monteriggioni
Monteriggioni is a must-stop on your Tuscan road trip. This walled castle nestled on a hill in the province of Siena is one of the best-preserved examples of a Medieval town. You can still walk along the walls and towers just like guards did 800 years ago, and even try on some armor at the Armoury Museum (Piazza Alighieri 23).
Pienza
If you’re a Tuscan wine lover, you’ve probably already planned to visit Montalcino and Montepulciano on your road trip. But in between these wine powerhouse regions is the tiny, gorgeous village of Pienza in the southern Tuscan valley of Val d’Orcia. There are plenty of agritourism spots around Pienza, so it won’t be difficult to find a nice place to stay.
Considered the ideal city of the Renaissance, Pienza is a great place to wander around and just take in the architecture. When in the village, you’ve got to try Pienza pecorino cheese! Hand-rolled pici is also popular here, so enjoy the best of both worlds when you have the cheesy pasta dish pici con cacio e pepe.
Planning and logistics for your Tuscan road trip
Now that you know you want to go on a Tuscany road trip, there are a couple of things you should know about renting a car and booking places to stay overnight.
While we love winging it, there’s a chance that you won’t be able to get a car or a local room due to low availability. So to avoid strife and miscommunications across the language barrier (and paying premiums), you should consider at least booking your rental car and figuring out where you want to stay before you hit the road.
Booking a rental car
If you have a valid driver’s license from your home country you should be able to drive in Italy as a tourist. However, some car rental agencies might prefer it if you have an “International Drivers License”, which you can easily get online or through your car insurance.
Many car rental agencies you’ve heard of like Hertz and Enterprise have locations in Italy. There are also local chains like Europcar. The cost of renting a car can vary depending on the company you book with and the season, so plan to spend $50-$100 per day.
Expert’s Tip: If you don’t know how to drive a manual stick shift, be extra sure you request an automatic transmission!
Where to stay
Sure, there are plenty of hotels to stay in in Tuscany, but when exploring the less frequented areas on your road trip you should try a family-owned B&B or agritourism. The local places are going to be smaller, so definitely book them ahead of time to ensure you get a room.
Many locations are listed on Airbnb, but that might not be the most budget-friendly option. In Italy, the third-party booking website Booking.com has loads of hotels, agritourism, or vacation homes listed. You can also head directly to Agriturismo.it if you know you want that hyper-local experience.
Verity Pryor-Harden is a freelancer of many talents living in the historical Tuscan city of Arezzo while studying Visual Communications in Florence. She’s a sucker for a cold spritz in a piazza on a hot day, enjoys making bizarre wine pairings, and is a Tuscan street food enthusiast. Follow along on Instagram @verityeph.