Beat the crowds by starting your day at the Basilica of Saint Francis, a UNESCO World Heritage Site and favorite of pilgrims and art aficionados. Visit with a guide to fully appreciate the historic and artistic significance of this 13th-century complex built above the saint’s tomb and frescoed by Giotto and Cimabue.

From the basilica, move on to Assisi’s medieval old town, where Francis was born. The compact center is peppered with ancient Roman ruins and sacred Franciscan sites; you can take in the town’s highlights—from the Temple of Minerva to the Basilica of St. Clare—with a walking tour in just a few hours.

After a day of food for the soul, it’s time to feed the body. Unwind with an informal evening wine tasting to sample Assisi’s excellent local labels paired with regional cheeses and prosciutto, a delicious way to appreciate the more secular side of Assisi.

Dedicate your second day to enjoying the local cuisine. Early risers can join a morning truffle hunt, visit a winery, tour an olive oil mill, or dive into a hands-on cooking lesson—all followed by lunch featuring regional delicacies and traditional dishes.

If you’d rather take advantage of your second day to head farther afield, you can combine a wine tasting with a jaunt to one of the many picturesque hill towns in Umbria and Tuscany. Tour the historic center of Orvieto or Montepulciano and sample their prestigious local wines on a guided day tour from Assisi.

End your time in Assisi by relaxing in the hilltop historic center as the sun sets over the valley. Grab a spot on the scenic overlook in Piazza Santa Chiara, or climb to the Rocca Maggiore fortress above town for unparalleled views across the rooftops to the Umbrian countryside beyond.