NEW YORK

The vibe: Enter the luxurious lives of Manhattan’s elite with a weekend getaway that lets you stay (and dine and shop) like a Gossip Girl.

Stay: At the corner of Madison Avenue and 50^th, the New York Palace combines old-fashioned luxury with cutting-edge culture cred: Gossip Girl’s Serena van der Woodsen lives with her mother in one of the hotel’s four triplex apartments. The building itself is an architectural gem, incorporating the site’s original 1882 Villard mansion and the 55 storey tower built by Harry and Leona Helmsley in 1980. The hotel’s aesthetic forgoes fashionable chilly minimalism in favour of Gilded Age splendour: think chandeliers, Classical frescoes and carpets thick enough to sleep on. Book a room in the exclusive Towers suites (located in the top 14 floors) for the city’s best views of St. Patrick Cathedral’s gothic spires and Manhattan’s Art Deco skyscrapers (newyorkpalacehotel.com).

Dine and drink: After a day on nearby Fifth Avenue, enjoy one of the Palace’s signature cocktails at Palace Gate, located on a rare stretch of undeveloped Manhattan real estate in the hotel’s courtyard. Menu favourites? The Gossip Grill, a gourmet grilled cheese sandwich made with fontina and black truffles, and the city’s best fries, brushed with truffle oil and served with garlic aioli.

To really experience life
à la van der Woodsens, order the tasting menu at Gilt, the hotel’s opulent two Michelin-starred restaurant. The cuisine is superlative — the tandoori-spiced black cod served with roasted eggplant and toasted coconut is a standout — and a crack team of waiters move with the silent efficiency of culinary assassins (giltnewyork.com).

Do: Fifth Avenue is one of the world’s top shopping destinations — and you won’t need to load your bags into a cab to get back to the hotel. Hit the usual A-list favourites: Prada, Fendi, Tiffany’s, Bergdorf’s, Saks. (Tip: Check out H&M and Zara, too: their Fifth Avenue outposts have great fashion-forward pieces at their usual fantastic prices.)

Bleeker Street in the West Village has more of a boho vibe, with tiny cheese and pastry shops (including the famous Magnolia Bakery) and the city’s best Marc Jacobs store.

Getting there: Porter Airlines lets you fly in style. Leave from Toronto’s island airport, sip a complimentary cappuccino and arrive at Newark International Airport an hour and a half later. Book at flyporter.com.

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OTTAWA

The vibe: Experience the culinary renaissance underway in the nation’s capital, where a new emphasis on organic, local cuisine is revitalizing the city’s downtown restaurant scene.

Stay: Like a French Renaissance chateau dropped in the middle of downtown Ottawa, the stately Fairmont Chateau Laurier is a short walk from Parliament Hill, the Rideau Canal, and the bustling Byward Market. The building’s elegant limestone façade and turrets are complemented by grand, high-ceilinged rooms,
  antiques, brass railings and marble floors, reflecting the Chateau’s rich history as one of the jewels of the old CP Rail hotel chain (www.fairmont.com/laurier).

Dine and drink: There are newer hot spots, but Domus Café in the Byward market continues to set the bar for innovative regional dishes in a chic bistro setting. The menu changes frequently, highlighting seasonal produce and local livestock. Delicious mains include a coast to coast sustainable fish selection featuring Wild BC Sockeye Salmon, Halibut and Pickerel, and the Grilled Quebec Maison du Gabbier Elk chop served with cranberry chutney and King mushrooms. Dessert offers highlights such as the mille feuille layered with Ontario strawberries and rich crème anglaise (www.domuscafe.ca).

Do: Take a morning stroll in the Byward market to check out the outdoor food stalls offering fresh fruits, veggies, fish, artisanal cheeses and more. Spend your afternoon in the rarefied haute cuisine atmosphere of Le Cordon Bleu Ottawa, which offers an assortment of one-day and half-day courses, including gourmet pizzas, delicious sauces and classic French cooking (www.lcbottawa.com)

Getting there: Book at
flyporter.com.

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CHICAGO

The vibe: Paint the town red (and yellow and ochre) in one of the world’s premiere destinations for modern art.

Stay: The recently refurbished Four Seasons Hotel Chicago (www.fourseasons.com/chicagofs) occupies 17 stories of one of the Windy City’s tallest skyscrapers, offering stunning views of the cityscape and the shifting hues of Lake Michigan. The Museum of Contemporary Art and the Art Institute of Chicago are both within walking distance, as is North Michigan Avenue’s famed Magnificent Mile shopping district, home to Chanel, Buberry, Max Mara and Neiman Marcus boutiques.

Dine and drink: Molecular gastronomy tends to attract the snobbish set, but Alinea Restaurant (www.alinea-restaurant.com), which is at the forefront of the culinary trend, is welcoming both in vibe and price. Try the tasting menu, a symphony of 13 courses of deconstructed flavour palettes, like shell crab with carrot, five spice and duck, and sweet potato with bourbon, brown sugar and “smoldering” cinnamon.

Do: Between them, the Art Institute of Chicago and the Museum of Contemporary Art contain one of the most amazing, diverse collections of modern and contemporary paintings and sculptures in the world. Featured artists include Cezanne, Monet, Dali, Picasso, Warhol, Francis Bacon, Jasper Johns, Chuck Close and many other iconic figures displayed alongside hundreds of lesser known and emerging names. Make sure to devote at least a few hours to each museum, and wear comfortable shoes.

Getting there: Porter has daily flights to the city’s Midway Airport, a short bus ride from downtown.

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