My idea of heaven still is to drive the gravel farm roads of Umbria and Tuscany, very pleasantly lost.
- Frances Mayes
The so-called Green Heart of Italy, Umbria is an untouched region of unfathomable natural beauty in the central part of the country. With endless stretches of lush green forests, dreamy rolling hills, and picture-perfect medieval towns and villages, landlocked Umbria is known for its exquisite cuisine, superb local wine, and authentic ambiance. A road trip across Umbria's gorgeous scenery, complemented by a stay at a historic mansion in the heart of a quintessentially Italian town or a farm stay amidst the region's spectacular countryside, is the best way to get to know one of Italy's last remaining off-the-beaten-path regions, a true gem waiting to be discovered.
Inhabited since the Stone Age, Umbria rose to fame for being the birthplace of Saint Francis of Assisi, a Catholic friar who founded the Order of the Franciscans in the early 13th century, rendering Umbria the synonym for spirituality in Italy. Nowadays, unlike neighboring Tuscany, Umbria remains an under-the-radar region, ideal for anyone looking to experience the real Italy beyond the country's mainstream destinations.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of our Italian vacation packages, based on 211 reviews

I would highly recommend Jayway. You were so accommodating and helpful throughout the entire experience. Thank you.
– Gail, Annette & Jody, Georgia
Year : 2026
Visited : Italy
Itinerary : Castellina in Chianti
Rating :
Visited : Italy
Itinerary : Castellina in Chianti
Rating :
5 / 5

Every detail came off great especially the transportation. Also we knew we had attentive help if any changes or issues arose.
– Joan, Gary, Kinta & Peter, Connecticut
Year : 2026
Visited : Italy
Itinerary : Sorrento, Siracusa, Taormina
Rating :
Visited : Italy
Itinerary : Sorrento, Siracusa, Taormina
Rating :
5 / 5

We had an outstanding experience working with JayWay Travel for our trip to Italy. They were incredibly thoughtful, professional, and making the entire journey feel seamless and personalized, like having a trusted friend helping plan the perfect vacation.
– Paul, JoAnne, BonniJo, James, Daniel, Leah & Walker, Michigan
Year : 2026
Visited : Italy
Itinerary : Rome, Florence, Lucca, Florence, Sorrento, Rome
Rating :
Visited : Italy
Itinerary : Rome, Florence, Lucca, Florence, Sorrento, Rome
Rating :
5 / 5