When drummer and former Late Night with Conan O’Brien bandleader Max Weinberg, 72, isn’t on the road touring with Bruce Springsteen and the E Street Band, odds are you’ll find him and his wife, Becky, in their adopted hometown of Cortona, Italy. For years, Weinberg and his family savored time spent at their Italian villa on the border of Tuscany and Umbria. After their children grew up, he and Becky traded that isolated location for a 900-square-foot apartment in the nearby walkable town of Cortona. “Particularly as seniors, the pace of life’s an incredible contrast to the frantic pace we sometimes live through in the States,” Weinberg says. “It’s also a great place for me to unwind and still savor the essence of a simple, somewhat country life.” He shares his suggestions for the best places to stay, dine and explore in and around the region.
Book your stay …
There are many [bed-and-breakfasts] within and outside the walls of Cortona. … Our friends like to stay in town at the Hotel San Michele on Via Guelfa. You don’t need a car, and by the second day you are fully in the swing of relaxed Italian country living.
Le Terre dei Cavalieri is an incredible country estate where you can stay in the main villa or your own cottage on the grounds, enjoy simply delicious meals prepared in the classic Tuscan/Cortonese style, and even participate in top-notch cooking classes.
Indulge in delicious dining …
One of the notable elements of Cortona is that there are dozens of incredible restaurants. ... La Bucaccia [is] where Romano Magi, the owner, nightly makes a special presentation of his delicacies.
[Trattoria] Dardano is another spot we regularly hit. The Castelli family grows their own produce and farms the livestock from which they create the famous Tuscan specialties like crostini neri and the world-famous Florentine steak of the Chianina (“white cow”) beef.
A must in Umbertide (24 miles away) is [The Locanda di] Nonna Gelsa which, unlike many Italian restaurants, is open on Mondays. Chiara and her family are the best hosts, and you will delight in the absolutely authentic country preparations. It’s a magnet for people who have really dug into the area and ventured off the beaten track. New Year’s Eve at Nonna Gelsa is a Weinberg family tradition!