Discover a Romantic Hilltop Retreat in Italy: A Peaceful Escape from Rome’s Bustle

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Discover a Romantic Hilltop Retreat in Italy: A Peaceful Escape from Rome's Bustle

Italy overflows with romantic destinations, but unfortunately, some — like dreamy Venice or gallant Rome — come with urban noise and chaos. For a quieter escape that still delivers in the romance department, consider the town of Assisi, 17 miles east of Perugia in Umbria’s rolling hills, reachable by train from all major Italian cities. Just three hours by train or two hours by car, it’s the perfect escape from the crowds of every-popular Rome. Assisi is not your average everyday Italian hilltop paradise. It’s the birthplace of St. Francis, one of the world’s most venerated holy beings, known for a connection to nature so strong it was quasi-mystical. 



Though St. Francis died in 1226, his presence remains strong throughout the area. It lives on in the town’s magnificent artwork, such as the Giotto frescoes in the Basilica of San Francesco that depict his amazing life, and in the hauntingly beautiful abbeys, hermitages, and sanctuaries. For the non-religious, his ethos endures as the bridge between the human and natural worlds — in the place where cobblestone streets meet gentle green pastures, where tall cathedral spires touch pink sunsets and the blinking brilliance of the night’s stars. The enchantment even emanates from the sublime cuisine, prepared by locals with vegetables grown tenderly in Assisi’s land, where the humble saint and his companions once tread barefoot. 

Discovering the magic of Assisi and the surrounding area

Not everyone who comes to Assisi knows the story of St. Francis. But all will feel the magic when wandering the town’s enchanting cobblestone alleyways and strolling through the Piazza del Comune, which boasts ancient buildings like the Temple of Minerva. Even non-believers will be awestruck by the artwork in the town’s most famous religious site, the Basilica of San Francesco, with paintings by Pietro Lorenzetti, Simone Martini, Cenni di Pepi (otherwise known as Cimabue), and Giotto di Bondone. Those willing to climb the steep Asio hill to a medieval fortress, Rocca Maggiore, will be rewarded with a sight as spectacular as any painting. From the towers of the fortress, one can gaze down at the basilica, the town, and the brilliant emerald landscape, spreading out in every direction. 

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Just outside Assisi, the surrounding hills and woodlands await, offering their own soft spells. It’s possible to explore this terrain on foot on local trails or in a private vehicle to travel further up into the mountains. One not-to-miss excursion is to Mount Subasio to visit the Eremo delle Carceri, a forested area with caves where St. Francis and his followers would go to meditate. Today, it’s the site of a beautiful monastery along with the serene Grotto of St. Francis, where the saint prayed, preached, and slept on a simple stone bed. 



Where to eat and relax in Assisi

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.