OCCUPATION: Mother

MY STYLE: I like simple, classic, and comfortable clothes, shoes, and bags. Favorites include Vanesa Bruno, Zadig et Voltaire, and Lanvin for evening dresses. I’m addicted to J Brand jeans with comfortable boots during the day; and at night, dresses, high heels, and very few accessories.

I LOVE MILAN BECAUSE: It’s a working city, but Milan is also small, so moving around with kids is easy, especially on bicycles.

Castello Sforzesco

Among the largest citadels in Europe, this 14th century castello was once home to Milanese dukes, not to mention Spanish and French conquerors. Today, Castello Sforzesco houses several Lombardy-region art collections and museums. Find your way to the Sala delle Asse, where you can find a ceiling painting by Leonardo da Vinci, one of the castello’s few remaining original decorations.

Cova

Opened alongside Milan’s La Scala Theater in the early 1800s, this legendary café has seen its share of actors, playwrights, musicians, and public figures—as well as devastating WWII turmoil. Today, the legendary pasticceria has opened up several offshoots around the world, but the locale on Via Montenapoleone (now housed in a different, post-war building) remains a particularly glamorous spot for sweet raisin panettone and people-watching.

Centro Ippico Lombardo

One of the top riding schools in Italy, this academy offers pony classes for younger children, and jumping and dressage for advanced students (north of age 12). Centro Ippico Lombardo is also known for its involvement in federal hippotherapy programming, a practice that’s used for physical, occupational, and speech therapy.

La Briciola

In recent years, La Briciola has become the alleged hangout for Italian soccer players, but the restaurant’s high arched ceilings, lauded menu, and vibrant social scene started attracting the local glitterati long, long before. The owner, Gianni, has made a bit of a name for himself as Milan’s best party host. In the midst of all the buzz, be sure to give the beef carpaccio, tagliata con patete e carciofi, and tiramisu a try.

Antonia

An extension of her own style and vitality, Antonia Giaenti’s trendy Brera boutique is stocked with a hand-selected assortment of her favorite labels—ranging from Balenciaga and Missoni to Edun and Boy by Band of Outsiders. Wander next door to Antonia Accessories, a veritable temple to footwear, bags, and small leather goods. For those who can’t make it to Via Ponte Vetero, the boutique’s website (which also functions as a well-curated music playlist) is also worth a visit.

Peck

Truly a food institution, this multi-story gourmet market began as a delicatessen in 1883. Its legacy products (top-shelf designer meats) are housed on the main floor, along with cheese (there’s an entire section devoted to parmesan!), oils, pastas, truffles, mushrooms, caviar, and foie gras. The jams and honeys, complete with gorgeous packaging, make for an especially good gift. If you’re looking for a sit-down experience, the topmost floors are home to a wine cellars and a stylish café.

Il Resentin

Located in the arty Brera neighborhood, this small inn has only four rooms available—each decorated with an attention to detail that only a venue of this size could pull off. Ask the concierge for a vintage bicycle to use around the city, and visit The Kitchen restaurant for delicious, family-friendly Italian fare. For the adults in the group, we recommend the inn’s speciality: a traditional Venetian digestif of grappa with espresso.

Giardini di Via Palestro

Perhaps better known as Giardini di Palestro, this romantic and heavily wooded park is the oldest in town. Within its maze of sculptures and trees, you’ll also find pony rides, trails for walking and biking, and a café for a mid-stroll snack. If  that’s not enough, you can continue your walk through the gardens of the Villa Reale and Galleria Nazionale d’Arte Moderna.

Giacomo Arengario

While the interiors at Giacomo Arengario pay tribute to art deco fashions (geometric patterns on darkly lacquered wood), the food pays tribute to classic, perfectly executed Milanese dishes. Considered a sequel of sorts to Giacomo Bistrot, Arengario is situated amid all the hustle and bustle—its windows overlooking the romance of the Piazza Duomo. Along with everything else on the menu, we recommend the tagliatelle coi funghi.