A winter road trip through charming Italian villages. Italy is perfect for exploring at your own pace, and there’s nothing like a road trip to discover its most enchanting villages. This route takes us through historic sites, picture-postcard landscapes, and corners that seem straight out of a fairytale.
We start from Rome and venture into Tuscany and Umbria, visiting:
Indice:
Pitigliano and Sorano
Villages perched on volcanic tuff rock, with narrow streets and a medieval fortress.
Accommodation: Hotel della Fortezza in Sorano, inside the fortress, a unique experience.
Grosseto
A short walk through its historic center, surrounded by medieval walls.
Pistoia, Montecatini Terme and Montecatini Alto
Medieval squares, cobbled streets, and thermal springs from another era.
Accommodation: Fattoria di Capezzana, a farmhouse perfect for exploring the area at a leisurely pace.
Vinci
Birthplace of Leonardo da Vinci, with viewpoints and historic alleyways.
Chianti
- Montefioralle: a small medieval village, frozen in time.
- Castellina: medieval tower, viewpoints and cobbled streets.
- Rocca delle Maccìa: winery surrounded by vineyards and gentle hills.
Arezzo y Cortona
Historic cities with medieval architecture and spectacular views.
Accommodation in Arezzo: Hotel Il Portico, centrally located and comfortable.
Val d’Orcia
- Montepulciano, Pienza, Monticchiello, San Quirico, Radicofani, and Castiglione: landscape and history intertwine amidst hills, vineyards, and medieval villages.
Accommodation: Borgo Sant’Ambrogio, an ideal agriturismo for enjoying tranquility.
Orvieto
The final jewel, perched atop volcanic rock, with its imposing Duomo and Etruscan tunnels.
Accommodation: Hotel Virgilio, opposite the Duomo, a perfect location.
The trip is especially enjoyable in winter: fewer tourists, peaceful landscapes and a unique atmosphere.
Trayectis: the ally that made our trip perfect
Renting a car with Trayectis was one of the best decisions of the trip. They operate as a personalized service for international travelers, with attentive service from the very first contact.
- They pick you up at the airport and deliver the car to you without any hassle.
- They include full insurance, which is essential when you rent a car.
- They offer a spacious minivan for families with full insurance included, WhatsApp assistance in your language, useful for questions before your rental as well as some specific ones on the road.
- New units, personalized car deliveries and collections.
- Extra services: cooler, mate and other items that you can’t normally bring from home.
Thanks to Trayectis, we can focus on enjoying the towns, the scenery and the gastronomy, without worrying about anything logistical.
Special discount: 5% OFF using the coupon EUROPAACOMPANADA5 or mentioning that you are coming from Europa Acompañada.
Final tips for driving in Italy
- Plan access to the ZTL (limited traffic zones).
- Carry your international driving permit along with your driver’s license.
- Take advantage of the secondary roads, slower but full of charm.
- It has an internet connection for maps; we use Holafly eSIM. Discount code: EUROPAACOMPANADA5.
- Traveling slowly, stopping wherever you want and enjoying the scenery allows Italy to reveal itself in all its splendor.
Would you like to download our complete itinerary for a road trip through charming Italian villages in winter? [Download it here]
Video road trip through Italy
NOTE: The information in this article is based on our own experience and is completely objective. This article contains affiliate links.
