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 183 reviews

Everything was arranged for a seamless experience. All of our hotels, guides and experiences were top quality and I would definitely use JayWay again.
– Elizabeth, Darrin, William & Clara, Texas
Year : 2026
Visited : Italy
Itinerary : Venice, Florence, Rome
Rating :
Visited : Italy
Itinerary : Venice, Florence, Rome
Rating :
5 / 5

JayWay knows how to make vacations special and smooth. We planned as much as we wanted, and we were able to book what we wanted plus get ideas from JayWay about other activities that we ended up really enjoying.
– Lyndsi, David & Claire, Florida
Year : 2026
Visited : Italy
Itinerary : Rome, Sorrento, Naples
Rating :
Visited : Italy
Itinerary : Rome, Sorrento, Naples
Rating :
5 / 5

JayWay took care of the details of the trip leaving us with a worry free experience.
– Jane & Donald, Minnesota
Year : 2026
Visited : Spain, Italy
Itinerary : Barcelona, Cruise, Rome
Rating :
Visited : Spain, Italy
Itinerary : Barcelona, Cruise, Rome
Rating :
4.8 / 5