The contemplative hilltop village of Assisi became my home somewhat by chance in the 1990s—a dramatic departure from my previous life in fast-paced Chicago. In the years since, my love hasn’t waned for Assisi’s medieval old town and sweeping views across the surrounding valley.
Just as the region of Umbria is at the heart of Italy, the town of Assisi is at the heart of Umbria, both figuratively and geographically. By far the area’s biggest draw, Assisi is also centrally located and an ideal base for exploring all of Umbria. Here’s how to see the best of the town and its surrounding region in three days.
Assisi and its neighboring hill towns are marked by warm days and cool nights, so dress in layers.
If you only have time for one thing, make it the Basilica of Saint Francis, a UNESCO World Heritage Site and home to Giotto-school frescoes.
Assisi is best known as the birthplace of St. Francis, so begin your trip with the spectacular 13th-century Basilica of Saint Francis and the humble Porziuncola church. Avoid the crowds by visiting the basilica first thing in the morning to take in masterpieces by Giotto and Cimabue and the saint’s tomb.
Afterward, explore the rest of Assisi’s medieval center on foot, visiting highlights such as its Roman temple and Romanesque churches. Then, hire a car and explore the Franciscan sanctuaries and chapels on the slopes of Mt. Subasio and in the town of Santa Maria degli Angeli.
Devote your second day to Umbria’s culinary delights. This area is known for its excellent rustic cuisine, based on simple farm-to-table ingredients foraged and grown in the region’s hills. Begin the day by setting off with a local tartufaio (truffle hunter) to hunt wild truffles in the oak woods, followed by a truffled-laced countryside lunch.
In the afternoon, move on to a local winery to sample the area’s best red and white wines paired with local cheeses and cold cuts, or visit an olive farm to sample the region’s prestigious liquid gold drizzled over toasted bruschetta.
Take advantage of Assisi’s strategically central location as a convenient jumping-off point for day trips farther afield. Begin with the capital city of Perugia, home to magnificent Etruscan ruins and the storied Perugina chocolate factory. The city is reachable from Assisi by train or by car in about 30 minutes.
In the afternoon, explore one of the region’s atmospheric hill towns—Spello, Spoleto, and Montefalco are top options—and take in their Romanesque churches, cobblestoned lanes, and cultural gems, from Roman ruins to medieval frescoes. The first two towns are along the main train line, while the latter is reachable by car.