In the time it takes you to read this sentence, a hot new trend will be established in Milan. What Europe’s fashion and design capital may lack in good looks, it most certainly makes up in lifestyle. In a city where its populace worships at the temple of Prada and Versace, showing up in style is half the fun of knowing the hottest places to go. But while crashing the many fashion events and parties that take place annually around town may be practically impossible—unless your name is Brad or Beyonce—there’s nothing stopping you from soaking in the city’s cool vibe. From shopping at the chicest boutiques to sleeping at the most stylish hotels and drinking where famous rock stars have hung out, here we’ve rounded up the best the city has to offer so you can hit the ground running.

Where to Stay

Every city has its must-see sites and three of Milan’s iconic spots—the Piazza del Duomo, opera house La Scala and the Galleria Vittorio Emanuele, a popular gathering place for shopping and dining—are all within steps of these three classy hotels.

LUXURY Set in a 1870s classical palatial building, Park Hyatt Milano fuses understated Italian elegance with a Zen atmosphere. The 117 luxurious guestrooms feature Travertine marble floors and walls, high ceilings and minimalist lines accentuated by rich materials, state-of-the-art Bang & Olufsen sound systems and free Wi-Fi Internet access. Dining at The Park restaurant is an experience not to be missed. Divided into three sections, the menu features regional, national and fusion dishes that focus on seasonal products and are paired with an exclusive selection of Italian vintages. Get pampered at the hotel’s spa, which features holistic treatments, steam rooms and a fitness center.

FASHIONABLE The Gray features 21 distinctive rooms, in neutral palettes offset by vibrant splashes of color (burgundy, fuchsia), and outfitted with down bedding, flat-screen plasma TVs, CD/DVD and hydro showers or baths. To feel like a star, book yourself into a bi-level apartment suite featuring a private gym or steam room.

HIP Intentionally designed by fashion designer Vincenzo de Cottis to feel like an art installation and work in progress, Hotel Straf is all scratched mirrors, polished cement floors, burnished brass and recycled fiberglass panels. Do like Moby or John Malkovich and reserve one of the sixth floor suites with views of the Duomo from a private balcony. The rotating artwork in the lobby is chosen to reflect the city’s important events (Fashion Week, Design Week). Trendy locals mingle with hotel guests over happy hour cocktails and light bites at Bar Straf.

What to Do

SHOPPING Before you max out your credit card at Gucci and Dolce & Gabana in the city’s most elegant streets (Via Montenapoleone and Via della Spiga), head over to 10 Corso Como. This 13,000-square-foot complex is designed around a beautiful courtyard that leads to a photo and design gallery, a bookstore and CD store, a boutique featuring luxury goods and hard-to-find men’s and women’s clothing labels and a café. Also within the complex is 3Rooms, an uber-chic B&B featuring private entrances to three separate apartments decked out in vintage designer furniture by Arne Jacobsen, Eero Saarinen and Charles and Ray Eames among others. A more alternative crowd shops for vintage threads and custom shoes at edgy boutiques on the strip along the ancient Roman columns of San Lorenzo in Corso di Porta Ticinese.

DOWNTIME If you need a respite from the busy Milan streets, take a breather at Parco Sempione where locals flock to at lunchtime for a quick siesta on park benches surrounded by beautiful lakes, bridges and meadows.

NIGHTLIFE The park scene picks up the pace after sunset at Just Cavalli Café, where fashion designer Roberto Cavalli has created an ultramodern glass temple of cool perfect for the see-and-be-seen crowd. The best time to go is in the summer when the outdoor Just Flower Garden lights up with torches and candelabras. Claim a sofa and spend the evening sipping designer cocktails accompanied by fresh antipasti while the house DJ mixes downtempo grooves.

ART & CULTURE Next to Park Sempione is La Triennale di Milano, a modern art and design museum that recently featured a Basquiat exhibition. Housed in a converted historical tramway warehouse in the Ticinese neighborhood, Forma is an exhibition space, bookstore and café displaying the work of today’s most exciting photographers. • On the last Sunday of every month, head over to Mercatone del Naviglio Grande, a colorful exhibition market showcasing antique furniture, books and jewelry along the banks of the city’s most ancient canal. Every year, opera season kicks off at La Scala on December 7, the city’s patron saint’s day (Saint Ambrose). • Book well ahead of your visit if you plan to view the Last Supper. A city sightseeing tour by bus ($50) guarantees admission to Leonardo Da Vinci’s masterpiece as well as the Cathedral and the Scala Theater and Museum among other sites.

EXPLORE Behind the Garibaldi train station is Isola, an up-and-coming neighborhood inhabited by the city’s artists, bohemians and musicians. Take in a show at the Blue Note jazz club or grab a drink at one of the quarter’s artsy cafés

Where to Eat

Fashionistas flock to the pedestrian-only Corso Como, which is lined with hip eateries and bars.

DINNER The best time to reserve a table at Alla Cucina Delle Langhe (Corso Como 6) is in October and November,at the peak of mushroom season. But you can never go wrong at this romantic restaurant that specializes in refined delicacies, like truffles and red wine, from the Piedmont region.

LUNCH On the go locals stop at Panino Giusto for the best sandwiches in town. With five locations close to the most popular tourists attractions, this is a sure bet for a tasty and affordable meal.

BRUNCH This American weekend mainstay is given the Italian touch at the exclusive Bulgari Hotel, where chefs whip up marvelous soups, salads, Mediterranean-style pastas and individual desserts for a jetsetting crowd.

WINE BAR A friendly and knowledgeable staff pours the best wines from Sicily, Sardinia, Tuscany and Piedmont and pairs them with salads, cheese and salami plates at Il Cavallante (Via Muratori 3), a new trendy enoteca.

GELATO Chocoholics make a beeline for Choco Cult, a concept store featuring art, wine, sumptuous desserts and exotic chocolate ice cream flavors (think chocolate with chili or rum).

APERITIVI The early evening cocktail is an institution in Milan where, for the price of a glass of wine, beer or expertly mixed cocktail, you get to sample a variety of Italian finger food. A mixed crowd of twenty-somethings, models and executives flock to Corso Sempione, a lively street lined with a number of happening bars. Do like Mick Jagger did and sample small panini, pastas and bruschetta at Wish (#5) or hang out with a more laid back crowd at Deseo (#2). Wherever you end up, make sure to try a Negroni Sbagliato, the iconic cocktail featuring vermouth, campari and spumante instead of gin. A more sophisticated crowd sips Dom Perignon and Krug Grande Cuvée at the Hyatt’s Park Bar, where cocktails are paired with sushi, crudités and canapés.