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As the only hotel inside the city’s famed 19^th-century Galleria Vittorio Emanuele II (the oldest shopping mall in the world), the place is in a league of its own, from the building’s hand-painted vaulted ceilings and original frescoes to touches like grand pianos in the rooms and the racing-green Bentley Continental Flying Spur that whisks guests around the city in style.

There are 24 rooms in total, though the tall ceilings and mezzanine levels make them feel much more like private apartments than rooms. Designer furnishings and high-tech amenities complement the building’s original features and antiques, and guests get their own professional butler-concierge (all languages catered for), a choice of bed linen and pillow type, and as much vintage wine and champagne as they can handle. Personal laptops and shopping trolleys from the best luxury brands are also available on request.

Isola has become Milan‘s hipster hangout, so you are going to want spend a lot of time here. Best way is sleeping over, and the Isola Apartments are key. Lots of light, minimal decor and all the trappings of home, the loft apartments are great for couples with kids or other kids of third wheels.

Bar Basso is one of the oldest cocktail bars in Milan. It’s appeared in many films and is a piece of history in the city. It’s always been a privileged meeting place for designers, journalists, artists, and writers. Here you can taste the best international drinks dipped in a real atmosphere of an Italian bar. Between the hours of 6 p.m. and 8 p.m., the Milanese file into their neighborhood bars and fashionable watering holes. They elbow their way to the bar and partake in one of the city’s long-held social traditions: the aperitivo. Strictly speaking, an aperitivo is a pre-meal drink served to whet your appetite or, as the Italians say, to “open your stomach,” commonly with drinks such as Campari and orange juice or Cinzano on ice.

Milan invented the art of bel cafè, the pedicured bar for a delicious morning coffee or afternoon aperitivo. Passerini has a delicious selection of pastries for mornings and afternoons, and is the ideal hideaway for an aperitivo in the city center.

Every city has an eatery that’s a mainstay for shoppers, and in Milan, it’s the tony Brera neighborhood restaurant Convivium. House specialties include complimentary rosemary flatbread, four-cheese pizza, and sea salt−encrusted sea bass for two. Via Ponte Vetero 21, 39/02-8646-3708.

When you walk around the Isola neighborhood, make sure to look out for street art. The colorful neighborhood is a tableau vivant for urban artists.

Isola is Milan‘s sleeper neighborhood because of its great location, hip shops and local vibe. It is also a great area to hang out in because, well, it feels like a neighborhood. Weekend street markets, clever graffiti, cute boutiques, artisanal shops and great bars. Add in there a strong sense of AC Milan fans and lots of people to meet, you’ve got your weekend.

A pleasant way to spend an evening in Milan is to stroll along the Naviglio Grande, a 12th century canal in the south of town. The warehouses along the towpath are now home to lively restaurants and bars. I recommend El Brellin. The second floor restaurant offers refined modern Italian fare with ambiance to match and the bar below gets busy on the weekends.

Italy’s No.1 chef Massimo Bottura described Nottingham Forest as a blend of “Hemingway and the TV show C.S.I.” for its eclectic vibe. But for its cocktails, Bottura and many others feel Nottingham Forest is Milan‘s main innovator. Mixologist Dario Comini just happens to be considered one of Italy‘s best bartenders, thanks to a great mix of creativity and risk.

Palazzo Mezzanotte (Mezzanotte Palace) is the seat of Italy’s stock market and a great example of 1930s architecture. Designed by architect Paolo Mezzanotte it was considered the most tech building of its time. 21st notoriety can claim artist Maurizio Cattelan’s comment to finance in the form of a large hand with extended middle placed in the very center of the piazza.

Artist Dan Flavin’s last installation is the Church of Santa Maria Annuciata in Chiesa Rossa, fondly known as simply Chiesa Rossa. Flavin’s light installation is a technicolor dream of electric hues across the main nave and central apse.

The newly opened Carlo e Camilla in Segheria is Michelin star chef Carlo Cracco adventure in family style chic cuisine. Everyone eats together on a long table in a former woodworking factory illuminated by Venetian chandeliers. The is a delicious interpretation of contemporary Italian cuisine including dishes such as spaghetti alici, cipollotto, lime e caffè (spaghetti with anchovies, green onions, lime and coffee).

Matteo Donini, aka the Don, opened his hidden art gallery in 2008 as a celebration of street artists, many of whom are his friends. If you find yourself in the Isola neighborhood in the late afternoon, ring the bell and see what happens.

We finally found it! Officine Del Gelato Milano; a modern, absolutely delicious gelato parlor. They had us coming back (three times in one day) until we had tried every flavor—including every kind of gelato popsicle. It was a guilt-free treat and every flavor was uniquely refreshing. We discovered this place, not from a guidebook but from the back of a streetcar. One evening we decided to let serendipity lead us, so we hopped on the first streetcar we saw. As we skidded past a gelato shop, we snapped a photo of a long and disorderly line of chatty Italians. The next morning, our last day in Italy, we made it our mission to find this place. Without knowing the tram line we had taken, we used our photos and collective memories to retrace our steps. While traveling, look for lines of locals because if they’re willing to wait, it’s bound to be good. I also learned that you can never have too much gelato. In the years since I’ve been back a few times and they’ve lived up to the memory—they even have new flavors. Mmm.

A. Caraceni is often described as the very best in Milan when it comes to tailors. At this shop, you’ll only find high-quality suits, impeccable cuts, and polished styles. The Caraceni tailoring legacy goes back more than a century, when the needle-working family was still in Rome. What followed was a line of talented tailors who have traversed continents to create beautiful suits. Everything at the store is hand-sewn, from formal smoking jackets to more casual hunting wear. Pick up a double-breasted jacket, the shop’s signature piece.