The Best Long Weekend Winter Getaways in (and Near) the US

For a romantic weekend away that doesn’t shy away from winter’s magic, Montreal won’t steer you wrong. Just an hour’s flight from NYC, the Canadian city feels worlds apart with its 17th-century cobblestone streets, rising restaurant and design scene, and distinct French flair. You’ll find Hotel Nelligan, a cozy boutique with exposed brick walls and in-room fireplaces, in Old Montreal, one of the city’s prettiest districts. The hotel is just a short stroll from Toqué!, whose dishes (crispy duck magret, for example) by native chef Normand Laprise helped put Quebecois cuisine on the map. New neighborhood bistro Marconi, across town in Mile Ex, is also earning rave reviews for its stellar cocktails and hearty cuisine (venison carpaccio; ricotta gnocchi; suckling pig belly). Montreal comes into its own during the winter season (this is Canada, after all!), so take advantage of cold-weather thrills like ice-skating on Beaver Lake and sledding in Mount Royal Park before thawing out during a tour of the Gothic Revival-era Notre-Dame Basilica. Don't miss Igloofest (January through February), an annual outdoor music festival held at the Old Port that’s been called “the biggest winter party of all time.”

It’s impossible to deny the beauty and allure of Colorado’s epic resort towns—especially come winter—but if you’re looking for something beyond the slopes, let us make a case for Denver. There’s more than enough in the state’s capital to make for a great long weekend escape, especially for foodies. The beautifully restored Union Station reopened in 2014 with a wave of new restaurants like Mercantile Dining and Provision and hotels including the Crawford Hotel, whose buzzy lobby moonlights as the train terminal and where some of its 112 rooms are modeled after Art Deco sleeper cars (in the best way). James Beard Award-winning restaurant Rioja, on Larimer Square, is a legend in Denver, famous for putting its fine-dining scene on the culinary map. The predominantly American menu takes strong cues from the Mediterranean in dishes like serrano wrapped octopus with fava beans and grilled ramps. Follow up dinner with drinks at William & Graham, an upscale speakeasy known for its creative cocktails that incorporate ingredients like cucumber beet syrup and sweet corn.

The sheer magnitude of twin-mountain ski resort Whistler Blackcomb is staggering. Its 200+ marked runs are enough to keep you on new trails for days—and don’t get us started on the après-ski scene. After carving the slopes, leave a day or two to check out Vancouver, a dynamic coastal city combining gorgeous natural city with a rising food scene. Check into the sleek new JW Marriott Parq Vancouver, then head on over to Granville Island and Edible Canada bistro, whose farm-to-table menu spotlights inventive Canadian cuisine. (Go for the Beef Shin poutine, which is served with cheese curd-topped fries and smashed sunchokes.) Still have money burning in your wallet? Gastown is a hotbed of indie boutiques. We love Orling & Wu’s artisanal crafts (Swedish rugs; British lighting) and Old Faithful Shop’s high-design/high-quality kitchenware.

The sheer amount of standout restaurant and hotel openings in Chicago continues to boggle the mind—and while a weekend will only allow you to scratch the surface of all there is to do and see here, a long weekend makes things more doable. First up: check in at The Robey, a buzzy new addition to Wicker Park. While its rooftop pool will unfortunately be closed (the season runs from May to September), its swank Up & Up cocktail lounge serves up seasonal libations like Grandma Charlotte’s Secret Recipe (made with graham cracker-infused bourbon with toasted marshmallow). After fueling up, it's time to plan your next move. We suggest doing some gift-grabbing (or treat-yo-selfing) at Penelope’s before a spin around the ice rink at Millennium Park and dinner at Macanese restaurant Fat Rice, which remains the forerunner of Chicago's "fusion" trend with its melting pot of flavors spotlighted in dishes like beetroot curry and its signature arroz gordo (a version of paella). Up for a classic "dinner and a show" combo? Head over to Pilsen and catch a comedy act, music performance, or even dancing at historic Thalia Hall.

Nothing beats the winter blues like flying due south. Four hours by plane from NYC (and just two from Atlanta) lands you in Nassau, the only city on the Bahamas. From here, it’s a quick and relatively cheap flight to Eleuthera followed by a 10-minute water taxi to Harbour Island, a tiny, quietly charming corner of the archipelago. Hole up at the new, exclusive, 11-room Bahama House—a 200-year-old plantation-style inn whose interiors are an elegant homage to the island’s colonial heritage (antique rattan furniture, canopied beds, coral-hued interiors that recall the island’s pink beaches, an outdoor bar stocked with rare rums). “Experience Managers” are on call to arrange whatever activity suits your mood, be it horseback rides on the beach, snorkeling with eagle rays and sea turtles, or, if you’ve booked a cottage, a French-Bahamian barbecue courtesy of a private chef.

There’s a certain kind of magic surrounding Arizona’s desert town of Sedona, famous for its surreal red-rock formations and luxurious wellness resorts that lure both spa-seekers and adventure travelers year-round. Winter is especially alluring, when snow dusts the landscape and its typically hot temperatures cool to a chill. Enchantment Resort, which enjoys a spectacular setting at the base of Boynton Canyon, is the perfect respite: its adobe-style casitas come with kiva fireplaces and oversized soaking tubs, while its heated outdoor pools remain open year-round. While outdoor pursuits may be too chilly to enjoy this time of year, dining inside is just as swoon-worthy at places like Mariposa, a Latin-inspired grill with jaw-dropping floor-to-ceiling views of the mountainscape.

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