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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.

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.

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.

This leather atelier off a leafy boulevard in the Porta Romana district is the epitome of chic. The only way to buy its coveted handbags and accessories, regularly spotted on celebrities, is to visit this white-hued, mirrored store. Designer Roberta Giacobbe crafts understated, heirloom-quality pieces including totes, iPad cases, and men’s carryalls using the finest quality leather. Each one is handmade in her workshop above the boutique. One of the most popular items is the zippered pochette (an envelope-shaped handbag), which can be custom-made in any color.

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 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.

Young artists stake their claim to the city’s open spaces.

Walk the Forum, queue early for the Vatican Museums, get reserved tickets for the Borghese Galleries. These and a host of other museums are all mind blowing. Stroll Trastevere, with Its vibrant local culture. Take a boat trip down the Tiber to Ostia Antica, Ancient Rome’s port city.Rome has cornered the contemporary arts scene for quite some time and now has two massive institutions to show for it, the Macro and the Zaha Hadid designed Maxxi.

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 Pirelli Tower is considered one of the most elegant “tall buildings” in the world, and at one point, it was one of the tallest. (And it was the tallest in Italy until 2010). The tapered, 32-story, 417-foot tower was developed in the 1950s by Gio Ponti with the assistance of Pierluigi Nervi, two of Italy’s best modern architects. The tower was also inspiration for the design of New York’s MetLife (formerly Pan Am) Building.

No Roman holiday would be complete without spending some time, at the very least, window shopping your way through the city. But it will be hard to stave off the urge to buy goods on some of the world’s best shopping streets. (Roads leading to the Spanish Steps tend to be lined with beautiful goods.) Rome’s shops sell exquisite delights from Italian designers, including leather bags, clothes and accessories (the eyeglasses at Ottica Spiezia will make you swoon), and much more. Of course, there are also plenty of food shops so you can bring home the tastes of Rome too.

A day trip to Lake Como from Milan is easy and worthwhile. Although we did not find George Clooney’s villa, we did find the lake-side towns of Menaggio and Verenna to be charming. With no prior planning we took a thirty minute train ride from Milano Centrale to Como San Giovanni and then boarded the public ferry a short walk away from the station. The ferry, preferably sitting on the open deck in the sun, is the best way to see the pretty little towns along the lake. Later we enjoyed a stroll and some lunch in Menaggio and then took another ferry across the lake to Verenna where we caught the train back to Milan.

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.

Galleria Vittorio Emanuele II is more than a shopping center, it’s a place for coffee, drink and dessert. Even more, in the center of the shopping center, there is a mosaic art of bull, which is said that if you spin your heel on the ball three times, it will bring you good luck. Of course a lot of people were spinning on the ball, and there is a hole on the mosaic art.

By one estimate, New York City is home to almost 8,000 restaurants—add in cafés and delis, and the count is closer to 24,000. This list is, needless to say, a mere starting point to the many dining rooms worth sampling, from an intimate Italian restaurant in the West Village to inventive small plates from chef-owner Ignacio Mattos on the Upper East Side.