When you need a break from the cutting-edge fashion at Milan’s first glamorous lifestyle shop, 10 Corso Como, stroll across the small courtyard to 10 Corso Como Café. Over lunch recently, sparrows flitted from table to table in a setting of mostly black-and-white furniture and linens, making the atmosphere feel like one out of an art film commissioned by Miuccia Prada. The guests tended to eat like birds as well—a colorful selection of crudités was delivered to every table, and the organic salad and pasta dishes were delicious but served in very small portions. The best time to come is around 6 p.m. for the aperitivi scene. You can also stay here at the upscale bed and breakfast, 3 Rooms.

A Michelin-starred restaurant that was opened by husband and wife food lovers in 1962, Il Luogo di Aimo e Nadia still serves delicious food in a slightly stuffy atmosphere. The family run spot, daughter Stephanie is passionately involved, has a cult status with foodies who are willing to make the trek (a 20-minute cab ride out of the center of town).

Even if you are not staying at the Armani Hotel, a drink at its serene Bamboo Bar on the seventh floor is a must. The soaring space is dominated by the onyx-back bar, the ambience is hushed and the views of Milan are expansive (from a few of the low-set tables, you can even see the Duomo). Come for an apéritif to sample some of the chef's small-plate food or make a night of it and transfer into the Armani restaurant, rewarded with a Michelin star in 2015.

The restaurant/bar at the Fondazione Prada was conceived by film director Wes Anderson and the warmth and whimsy it adds to the Rem Koolhaas–designed foundation is a strike of genius. Diners sit at color-blocked Formica tables surrounded by cheerful wallpaper and a long bar that holds everything from anti-pasta platters and Panini to large glass jugs filled with colorful candy and tiramisu served in dainty dishes. There's even a jukebox and a Life Aquatic pinball machine. Bar Luce is a good spot for a panino before or after touring the Fondazione. In the early evening, Bar Luce gets packed with a hipster-cool apero crowd.

Bentoteca, from one-Michelin-star chef Yoji Tokuyoshi, serves a fusion of Japanese-Italian cuisine in a sleek space. The dishes are great for sharing and paired with a selection of natural wines.

Recommended by Indagare Insider Bea Bongiasca

The perfect place for a coffee or a bite of pasta, salad or a sandwich. They have delicious baked goods, chocolate and tea and coffee.

Just as Paris has Café de Flore and Venice has Florian, Milan also has its classic café. Located in the Galleria Vittorio Emanuele and historically a favorite watering hole of Verdi and Toscanini, this spot is a Milanese classic that is part café and part museum. Opened in 1867 at the time of the Galleria’s inauguration and known until recently as Zucca or Caffé Miani, Camparino (now in partnership with the Campari brand) boasts historic interiors with wonderful mosaics and antique cabinets. Among its claims to fame: King Umberto the First declared that it served the city’s best coffee, and many still concur with his pronouncement. The best tables are outside but don’t miss a peek at the interiors.

This historic wine bar is known for its friendly and knowledgeable staff, plus the delicious wines that are paired with small snacks.

Sitting on top of the massive headquarters of fashion house Dsquared2, Ceresio 7 is one of the coolest places for an apéritif. The cool but cozy dining room and lounge was designed by cutting-edge Dimore Studio and draws a crowd of fashion and design people nightly. In the warm months, the rooftop terrace is unbeatable: cabana-style sitting nooks frame a large pool and the views are expansive. Starting at 7pm, the innovative cocktails are served with an array of fanciful snacks which are so beautifully prepared and plentiful (think salmon tartare, freshly sliced mortadella and lamb sliders) that they might even serve as substitutes for dinner.

Cucchi has drawn the city’s smartest and most stylish patrons for years and the people-watching is just as delicious as the old-fashioned pastries and Italian coffee.

Upstairs on the second floor of the Claska hotel, the Do boutique offers quirky reinterpretations of Japanese traditional crafts, as well as hosts regular design exhibitions frequented by the Meguro neighborhood’s most stylish denizens. This cult shop has spawned outlets across the city and around Japan.

With its old fashioned, almost Italian country grandmother, décor (tiled floors, pistachio green painted wainscoting, ceiling fans, globe lanterns and potted plants), Da Giacomo has been a beloved institution for years, and yet it draws a supremely fashionable crowd. The turn-of-the-century setting with stucco details and embossed wallpaper was created by designers Renzo Mongiardino and Roberto Peregalli to evoke the trattorias of a century ago but their conceit is retro at its best. Major designers like Giorgio Armani and Dolce and Gabbana dine here often on the Tuscan chef’s delicious cuisine. They come for some of the best fish dishes in the city and warm familiar service. Don’t miss the truffle offerings in season or the homemade desserts.

Opened in 2013 in Brera with a team of young cooks from all over the world and led by a Gualtiero Marchese-trained chef, Daniel has a huge open kitchen. In order to interact with clients the kitchen staff double as wait staff, a unique dining experience.

In Italy, even the sandwiches are slow food, especially the popular panini at De Santis. With De Santis’s 400-plus combinations, die-hard fans call it the best sandwich shop on the planet. Try the one with truffle, ostrich and foie gras or fresh shrimp, prosciutto and cream cheese

When Pisacco opened in 2013, it launched a veritable Milanese food revolution of smaller, hip eateries that blurred the lines between bar/aperitif and restaurant/dinner. Dry, located across the street, is the brainchild of the same owners and its genius blend of cocktail bar-meets-pizza joint remains a huge hit. There are devotees who consider this the best pizza in Milan.

The menu is small and mostly focused on delicious pizzas and focaccio, alongside some small-plate appetizers and salads. The cocktail list is substantial and runs the gamut from the classics (a mean Negroni or Martinez) to the esoteric (like the Lord Byron, a lethal concoction of Campari, bourbon, dry vermouth and a Benedictine herbal liquor). The room up front is where the action is, but it becomes a bit of a scene as the evening wears on, so travelers who want to enjoy a more peaceful dinner can also reserve a table in the serene dining room in the back.

They make a mean club sandwich as well as modern interpretations of classic light Italian fare and the atmosphere is hip and lively. Lots of people watching on offer with the option to sit in the piazza at the absolute center of Milano Moda.

Far from the city center (from most Indagare-recommended hotels, it's a 30-minute drive), this trendy farm-to-table restaurant is a must during the warmer months. Surrounded by a park and located along one of Milan's canals, it truly feels like a jaunt into the countryside. Owner Alice Delcourt is obsessed with all-things natural, organic, low-impact and biodynamic, which shows in the menu and wine list here. The garden setting is exquisite: how unexpected to be dining surrounded by flowers, herb and vegetable patches so close to the city center.

Menus change often and are completely focused around what's in season. Delacourt, who is French and has worked in restaurants in New York and London, has created a truly special place at Erba Brusca and her philosophy can also be seen in such lovely details as the row of red bikes that line the restaurant entrance, which diners can use for a pre-meal or post-meal bike trip along the canal.

If an insatiable desire for Japanese hits, head to Finger’s for fantastic Asian fusion and a great atmosphere. To excel in anything other than carb-heavy, cheese-infused dishes is difficult in Italy, but Finger’s does so excellently, and is definitely worth a trip.

The best spot to pass a few hours drinking espresso and reading art magazines is the Fioraio Bianchi Caffè, in the upscale neighborhood of Brera. One of several nice café’s on a leafy square this former flower shop still showcases fragrant blooms on almost every surface. By day it offers a selection of pastries and vegetarian dishes, and in the evening it’s a lively and happening aperitivi destination.

Fiat heir Lapo Elkann has transformed an old garage on the highway leading out to Lake Como into one of Milan’s coolest drinks and events spaces. The first floor has a cocktail bar with 1,000 model toy cars hanging from the ceiling and bartenders dressed in racetrack jumpsuits. Just beyond lies the ultimate showroom for car lovers. Contemporary art from the Gagosian Gallery shares the space with display boards exhibiting every custom paint color and interior material—from crocodile to Harris tweed—that you can choose to pimp out your Ferrari or Gulfstream.

This restaurant, which is located in the Museo del Novocento, was designed by the famous creatives behind Studio Peregalli, and while the Art Deco interiors are lush, it is the incredible views of the Duomo (which are best from the outdoor loggia) that are the real draw.

Baby sister of the famed Da Giacomo restaurant next door, Giacomo Bistrot is one of the few good restaurants open all day seven days a week from noon to midnight. Enter the old-fashioned bar with its massive mirrors, brass chandeliers and tiled floors and you may feel that you have entered a time machine and traveled back to a more elegant era, but the crowd that fills the cozy dining rooms of Giacomo Bistrot is thoroughly modern. Whether you sit in the library room with its walls of bookshelves or the private wine room, you will eat exquisite Italian food and be surrounded by Milan’s most fashionable crowd.

Also known as the Literary Café of the Royal Palace, this lovely hidden gem on the edge of Duomo Square is the perfect meeting place to have tea selected from Mariage Frères away from the crowds gathered at the Duomo Cathedral. Or come and read the selection of magazines with a cappuccino.

In the center of Milan, escape to Il Baretto for decadent Milanese dishes, excellent wine and spot-on cocktails. Signature dishes here include osso bucco, curried prawns and veal meatballs. On nice days, have your meal in the garden, where you’re surrounded by lush greenery.

Duck into this lovely place, off via Montenapoleone, for a quick lunch and people watching at its finest. Dine alfresco or in the wood-paneled dining room and afterward, be sure to stop by the adjacent shop to take away artisanal charcuterie and homemade pasta.

A favorite neighborhood restaurant of Brera residents, La Briciola is the passion project of the owner and chef Gianni Battista Valveri, who not only presides over the kitchen but greets his guests like old friends (which many are). The décor merges Italian bistro (mirrored walls and shelves of wine bottles) with bric-a-brac charm (framed photos of guests and collections of objects), while the menu focuses on simple, classic Italian dishes served to perfection. Carpaccio starters include carpaccio of avocados and hearts of palm or of artichoke. Whether you order buffalo mozzarella with cherry tomatoes, risotto Milanese, gnocchi, cacio e pepe or grilled fish, you may find it ranks among the freshest and tastiest you can remember.