Heather Carlson of Smitten with Italy is a great resource for travel to Umbria. She helps plan trips and also organizes tours—some designed around a festival with Letizia Mattiaci who runs beloved cooking classes in Assisi and was recently written up in the New York Times. Two such tours include one designed around Bevagna's storied medieval festival and another celebrating the olive harvest. Heather's website A Merry Feast is a treasure trove of how to get the most out of a trip to Umbria and beyond.