Umbria, Italy

Cycling off the beaten path. Umbria is a region of mountains and valleys, one rolling seamlessly into the other. The area that we’ll explore on this trip is a north-south strip where the Apennine Mountains begin their rise from the broad valley extending to its west. Along this line lie the towns of Perugia, Spello, Assisi, and Trevi, each built into the first line of foothills, each offering expansive views to the west and ready access to mountains that rise to the east. This junction of horizontal and vertical will be our playground for this trip, offering both immersive visits to medieval towns, and rides through forests, vineyards, and olive groves spread across hills that connect valley and high peaks. We’ll wind our way into and out of low mountains, lost in a peace far from the towns, then pop into bustling lanes filled with shops and restaurants. Our cycling adventures are the perfect complement to time spent exploring basilicas, fortresses, and narrow, walled lanes. Umbria is a place much off the beaten path, but so very much the essence of ancient Italy.

Perugia, Assisi, Trevi, and more. Umbria, the heart of Italy, is a captivating travel destination cherished for its rich history, serene landscapes, and authentic Italian charm. Nestled in the central region, this idyllic haven boasts medieval hilltop towns, each with its own unique story to tell. Assisi, renowned for its spiritual significance, is the birthplace of Saint Francis and Saint Clare, with the awe-inspiring Basilica of Saint Francis and the Basilica of Santa Chiara standing as timeless testaments to the town’s spiritual legacy. Perugia, the vibrant capital of Umbria, boasts a storied past dating back to the Etruscan civilization, evident in its well-preserved Etruscan walls, Palazzo dei Priori, and the Fontana Maggiore, offering visitors a glimpse into the city’s illustrious heritage as a cultural and artistic hub. Trevi, a quaint hilltop town, with its rustic charm and medieval origins intertwined with the production of high-quality olive oil, invites visitors to revel in its timeless allure, with narrow streets, medieval architecture, and picturesque piazzas creating an ambiance that captures the essence of Umbria’s rich historical tapestry.

A villa of our own. We’ll stay in a fabulous villa in the Umbrian hills between Assisi and Trevi, in a magnificent manor house surrounded by vineyards and olive groves.

Luxuriously furnished bedrooms with private baths provide personal space, while expansive indoor and outdoor common areas invite the group to assemble and share experiences. We’ll enjoy meals prepared in our gourmet kitchen, and we’ll lounge by our private pool or take walks through the gardens. Our home for this week will ground us and nourish us and bring us closer to the Umbria that those lucky enough to live here treasure. For one lucky week in Umbria, we’ll call this villa home.