During a trip to Italy with two other couples, we rented a VRBO villa in Tuscany for the first week of our stay. Our house, Cappella Di Pancole, was located in the hill town of Castelnuovo Berardenga, about 50 miles from Florence and 10 miles from Siena. After touring both anchoring cities and exploring the bucolic towns and villages around Castelnuovo Berardenga, we wanted to dip our toes into the nearby region of Umbria.

The six of us gathered around the farmhouse table in the villa the next evening. And we pinpointed the location of our villa on Google Maps and drew a circle to narrow our search. Over a bottle of Chianti, we looked forward to spending a day in Perugia. Creating an itinerary when traveling with a group always entails a process of negotiation that can feel daunting.