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Beyond the crowds of central SoHo—in a formerly industrial nook with historic roots on the edge of the Hudson River—a neighborhood is emerging: Hudson Square. This is the home of Hotel Hugo, a stylish loft-inspired retreat with an Italian spirit that has brought a bit of European-inflected flair to the neighborhood. This extension of SoHo has long been known by New Yorkers for its nightclubs, restaurants frequented by locals, and of course, the gorgeous Hudson River Park, an uninterrupted promenade that stretches the length of Manhattan. Now it has a chic hotel, complete with a rooftop that has a Cuban cantina vibe that serves cocktails against a backdrop of the Hudson River.

The Gastown neighborhood dates back to the Victorian era when “Gassy Jack” Deighton opened a saloon in a burgeoning sawmilling settlement. Now its grand heritage buildings—in Romanesque, Edwardian and Victorian Italianate styles—and brick-paved streets are home to art galleries, design shops and stylish eateries. Don’t miss the statue of the storied tavern owner in Maple Tree Square and Water Street’s famous steam clock, built in 1977, which sounds off every 15 minutes.

Cruise the Venice lagoon on one of the few remaining bragozzo boats still working this body of water. The vintage double-masted, flat-bottom fishing boat, once a common type of vessel here, dates back to 1946. The captain and owner, Mauro Stoppo, is also an excellent chef, which comes in very handy. Charter a daytrip (the boat comfortably carries 6–10 people) and sail to a lesser visited portion of the lagoon. The pace is slow; the food and wine decadent. If you want to charter a longer trip, you’ll explore more of the lagoon by day, learning its history and ecology, and then sleeping in private villas at night.

“This family-run restaurant on the fishing island of Pellestrina is quite far out—probably 45 minutes by boat. But in the summer months, it’s a lovely ride, breezy and fresh. Once you’re at the restaurant, you sit on a pontoon and see nothing but the spread of la laguna and the occasional boat speeding past. They do wonderful fish here. It’s incredibly fresh and they’ll bring you an array of mixed antipasti to start. The oven-baked turbot on potatoes with baby artichokes and baby tomatoes is fantastic. So, so good.”

Read about more of McAlpine’s Venice favorites.

Thanks to an owner and several staff members who hail from Italy, this Neapolitan-style pizzeria has an authentic feel that locals love. Its popularity shows—San Diego restaurants are rarely crowded, yet Buona Forchetta often boasts wait times of up to two hours. Much of the dining happens outside beneath an awning. Indoors, simple decor lets the gold Stefano Ferrara pizza oven shine. Go for perfectly blistered pies like the Nicola (mozzarella, mushroom, prosciutto di Parma, and truffle oil) or the Isabella (buffalo mozzarella, sun-dried tomatoes, onions, goat cheese, and rosemary). If Point Loma is more convenient, know that there’s a second, larger location called Officine Buona Forchetta in Liberty Station.

You may think Boutique Nadine has a bit of an identity problem. Not only does the shop have two locations just a few blocks from each other in the heart of Florence, but they are both part vintage-clothing store, part indie-designer boutique, and part midcentury-furniture emporium. In the plus column: Everyone finds something to love here. Clothing is arranged by color and walls are hung with classroom world maps. A long table, overseen by a crimson statue of Buddha, displays bowls of beaded bracelets and rings and trays of sunglasses. You may walk out with a vintage designer piece or a classic striped T-shirt, or shoes, bags, a bottle of Aquaflor perfume, or some pretty paper goods.

Wander along the souklike Via del Saracino until you come upon this large café with a great view over Positano’s main beach. You can have a cappuccino and pastry in the morning, a sandwich for a quick lunch, and then stop in later in the day for a cold treat. (The outstanding popsicles here are made from the juices of Amalfi lemons and other seasonal fruits.) It’s also a great spot to simply sip a beer while taking in the view of the action down on the Spiaggia Grande. For the sports fan, the bar’s multiple screens usually play baseball, soccer, and tennis.

The Palatine Hill was home to an early Roman settlement and had major significance for the city’s history. Legend states that Romulus founded Rome on that hill in 753 B.C.E., and Romans even maintained a cult site sacred to the founding father for about 1,000 years. When the emperors rose to power, they chose the Palatine as the location for their sprawling villas and built enormous marble-clad structures to showcase their wealth and power. Today, the ruins of their majestic estates rise above the Forum and Circus Maximus, reminders of the grand imperial past. A visit is included in the price of a ticket to the Forum or Colosseum.

This enclave on upper Boulevard Saint-Laurent in Little Italy emanates style from the front window on, with a quirky and impeccable approach to layout. Its rich wooden tables and modernist shelves are rife with unique, collectible objects and everyday useful things. Some are wearable, like silk scarves, merino wool sweaters and designer galoshes, while others exist to embellish living spaces, like beautiful metal bowls and hand-painted birch branches that serve as sculptures. There are even edible things, like artisanal lemonade syrup and fancy teas. The focus is on locally made goods with a smattering of international purveyors too, who fit within the store’s general earthy-chic aesthetic.

Maria e Susanna Sent has several shops where they sell their glass jewelry, the cutest one of them all just off the Ponte San Moisè in San Marco. This boutique is about as big as a broom closet, and that is certainly part of its charm. The real impact, though, comes from the jewelry this artistic duo started creating on the island of Murano back in 1993. Their line of mostly necklaces and bracelets is made in a unique process that creates murrine and filigree glass and plates in glass fusion. They also have shops in Murano and in Dorsoduro near the Peggy Guggenheim Museum.

Don’t let your eyes fool you. Villa Panza is a not just a gorgeous 18th-century estate. The villa and grounds host the spectacular Panza Collection, an amazing grouping of art from the 1960s through 1980s, with particular attention to American artists. The individual pieces (paintings, sculptures, drawings) are incredible but what makes the collection are the site-specific installations from artists such as Dan Flavin.

While exploring Burano, break for a fabulous seafood lunch at Al Gato Nero. The “black cat” restaurant is the creation of Ruggero Bovo, who has been cooking up some of the tastiest fresh fish and seafood here since 1965. “I love the fish of the Venetian lagoon and the Adriatic Coast, the raw material which has fed my island for generations and which I still have the fortune of getting fresh every day,” Bovo says. Fish and seafood are the star attractions on both the appetizer and main menu selections, but there are also options for vegetarians and carnivores. The pasta here is homemade, as are the delicious desserts.

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.

Located in a former rail services warehouse, Hangar Bicocca is a contemporary art space for site-specific projects funded by tire giant Pirelli. The space is more like a contemporary art concept that extends from the boards of its brick structure. The art gallery offers bicycle tours of the Bicocca area, as part of the “Bicocca Project,” a neighborhood reclamation project intent on showcasing the former industrial zone as vibrant neighborhood and equally vibrant arts scene.

Leoncavallo is both a cultural center and a concept. The buildings lining the run-down road are covered in amazing art by epic artists and upcoming writers. During the day, you’ll find photographers documenting the work or shooting for fashion mags and street art aficionados snapping the latest work. The building inside also gets painted by artists, local and international. Best way to get a peek is to visit for a project or concert.