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My Town: Max Weinberg’s Picks for Cortona, Italy

Musician shares his adopted hometown’s hot spots

spinner image buildings as background; photo of max weinberg in upper left corner; the words greetings from cortana, italy in upper right corner
Photo Collage: MOA Staff; (Source: Weinberg: Arturo Holmes/Getty Images; Background: Dario Garofalo)

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.


spinner image Outside view of hotel
The beautifully restored Hotel San Michele is located in the ancient Baldelli Palace and features 40 unique guest rooms.
Dario Garofalo

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!

spinner image inside of restaurant showing wine racks and tables and chairs; wine glasses and place settings on table
La Bucaccia restaurant uses the finest local and seasonal ingredients in their traditional Tuscan dishes.
Dario Garofalo


Take in the local atmosphere at …  

La Terrazza on the Piazza della Repubblica, which overlooks one of the main squares. [It] is ideal for a drink and a bit of people watching. You eat dinner and you go out for a stroll in the square, which is what they call the Piazza della Repubblica. You don’t just [go home and] turn on the TV.

spinner image max weinberg on a balcony with another building to his left
Weinberg, seen here at the Piazza della Repubblica, enjoys the culture, food, history and scenery that Cortona has to offer.
Dario Garofalo


Savor brunch at …

Tuscher Caffé on Via Nazionale. Try the macchiato and biscotti late in the morning or afternoon. Owned and operated for decades by Daniela and Massimo, the “pours” are as generous as the tourists and friends who gather there. 

At the top of the hill just past Frances Mayes’ astounding home, Girasole, is Caffé del Torreone. Definitely worth the hike. Have an espresso or acqua, sit outside and take in the vistas.

spinner image outside of tuscher caffé; man standing in front of door
Locally owned and operated for decades, Tuscher Caffé is one of Weinberg’s favorite brunch spots.
Dario Garofalo


Get your steps in …   

Our daily walk of a loop of nearly 3 miles takes us through the official formal gardens and park of Parterre. More French than Italian, actually, it resembles a mini Champs-Élysées. In the summer, open-air films and theatrical performances are held at the impressive though intimate stone amphitheater.

spinner image back view of max weinberg and wife becky walking on pavement with arm around each other; trees on both sides
Weinberg and wife Becky enjoy daily strolls through the park of Parterre.
Dario Garofalo


spinner image outside view of teatro signorelli theater
Visitors can enjoy operas, symphonies and jazz performances at Teatro Signorelli.
Dario Garofalo

Catch a musical performance at …

Teatro Signorelli, named after the great artist from Cortona, Luca Signorelli. The vast array of opera, small symphony and jazz performances offered, particularly from April to October, are world-class. I had the privilege of bringing my five-piece bebop group [The Max Weinberg Quintet] there for — I’m happy to say — a sold-out performance in 2017.


Revel in history at … 

Cortona itself is a vast museum. The churches and chapels spread out through the city contain ancient frescos, many by artists from the various so-called schools of Giotto [and Luca] Signorelli, [and there are] even Gino Severini modernist masterpieces.

The Museum of the Etruscan Academy and the Town of Cortona is a wonder to behold. Here you will find bronzes from the Etruscans three millennia in age, treasures from ancient Egypt, and sculptures virtually retelling the history and impulses of the Etruscan people.

The Diocesan Museum exhibits artwork by early Renaissance masters such as Fra Angelico, Luca Signorelli, Pietro Lorenzetti, Bartolomeo della Gatta. I’d also include gazing upon the work of Pietro Berrenttini, whose 17th century work bridged the gap between the Italian futurists and the leading Parisian avant-garde figures.

Outside the city walls is a monastery [Hermitage of Le Celle] … you can see the “Le Celle” where the late St. Francis of Assisi slept.

spinner image treasures of the museum of the etruscan academy on display
The Museum of the Etruscan Academy features 18th-century art and the latest archaeological finds illustrating the history of Cortona.
Dario Garofalo


Shop locally at …  

The two main viales (avenues) of the city are Via Nazionale and Via Roma. Here you find a bustling shopping area for food and wines, wonderful clothing shops, shoemakers, antique stores and, of course, shops for souvenirs and galleries of artwork. We shop in the square for everyday food items from Molesini, the grocery store and bottle shop owned and operated by Marco Molesini. The local merchants so appreciate the residents and visitors who frequent their shops.

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