8 Top Trending Destinations to Spend the Holidays, According to Experts

Despite its frigid temperatures, the Windy City offers plenty of charm over the holidays. Bundle up and join the revelers cheering on the Thanksgiving Parade or wander through ZooLights, where the Lincoln Park Zoo shows off thousands of twinkling lights, ice sculpture carvings, and more. If you get too chilly, retreat to the St. Jane Hotel on Michigan Avenue—a 1929 Art Deco dame with an inviting vintage fireplace, sweeping skyline views, and an American brasserie headed by lauded chef Aaron Lirette.

For an easy weekend of festive fun, head north to Toronto, which puts on an incredible Victorian-inspired Christmas Market in its cobblestoned Distillery Historic District for five full weeks. Expect to find handmade crafts, live music, and many cheerful Canadians drinking mulled wine. Want to step back in time? The 1914 Casa Loma—North America’s only full-size royal castle—is decked out in garland and lights for the holidays. Check out the poinsettia floral displays by candlelight at the Allan Gardens Conservatory, followed by a ride in a horse-drawn carriage or a sip of hot apple cider. If it’s too cold to stay outside, book tickets for a seasonal show like The Nutcracker ballet or a Home Alone concert by the Toronto Symphony Orchestra (December 6-7).

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Sure, you won’t find snow-dusted streets in the Big Easy, but New Orleans is still a spectacle come winter, when lively jazz bars croon Christmas tunes, twinkling lights dangle from iron balconies in the French Quarter, and high-end restaurants sling multi-course Cajun feasts. Base yourself at the Waldorf Astoria’s posh Roosevelt New Orleans, which transforms into a magical wonderland of 60,000 lights, 50 fresh Fraser firs, yards of garland, and thousands of hand-blown glass ornaments hung from a forest of birch trees. Its famous Sazerac Bar even gets into the spirit, serving Christmas-themed cocktails alongside intricate gingerbread villages by award-winning pastry chef Deborah Heyd.

Paris is romantic no matter what time of year, but there is something truly magical about being there around the holidays—just picture cozy French bistros, boulevards lined with icicles, and snow-dusted cruises down the Seine. Let's not forget about the shopping: the elaborate window displays at Printemps and Galeries Lafayette rival those along New York's Fifth Avenue. Take your s.o. ice skating hand-in-hand on the large rink in front of L'Hôtel de Ville or browse the 100 stands of local wares and French wine at the La Magie de Noël market in Tuileries Garden, next to the Louvre. 

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Minnesota gets a bad rap for its frigid, tundra-like winters, but the Twin Cities are quickly shedding the stereotype and becoming the region’s new capital of cool. Don’t miss The Great Northern Festival, a 10-day celebration that represents more than 150 years of local traditions including urban cross-country ski races, the U.S. Pond Hockey Championships, and the sprawling ice sculptures at the Saint Paul Winter Carnival. Thaw out at the Hewing Hotel, a 19th-century logging warehouse turned hip boutique hotel in the North Loop. It’s got a rustic, lodge-luxe look with exposed brick, leather lounges, roaring fireplaces, and original pine timber beams, plus a rooftop sauna and outdoor hot tub perfect for a warm dip on a below-zero day.

As travelers look east, Singapore is emerging as one of the hottest holiday destinations. The city celebrates with Christmas in the Tropics, a secular festival that revolves around its massive shopping scene. Entertainment districts like Marina Bay and Orchard Road—a two-mile stretch down Tanglin Mall—shine with light displays, while New Years’ countdown parties feature beachfront dances, fire-eaters, and more than 20,000 wishing spheres (huge floating balls covered with handwritten wishes that are thrown into the river). If you really want to splurge Crazy Rich Asians-style, reserve a room at the elegant Raffles Singapore, an 1887 institution that recently reopened with three new restaurants: a Mediterranean grill concept by Alain Ducasse, a French eatery by Anne-Sophie Pic (of the three Michelin-starred Maison Pic), and a contemporary Chinese restaurant touting a multi-sensory dining experience.

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Trade the snow for sand during a warm beach vacation in Florida. In previous years, tourists have flocked to Miami’s sexy shores or Orlando’s family-friendly parks, but Jacksonville is now garnering attention for its under-the-radar charm. The city is home to 22 miles of sugar-soft beaches and more than 30 reefs off the Atlantic coast, for those who want to soak up the sunshine. Meanwhile, you can get into the spirit during Winter on the Water, a two-month series involving craft fairs, an illuminated boat parade, and a lifeguard-chair decorating competition. The highlight, however, is WinterFEST; between November and January, Adventure Landing is transformed into an alpine village with a 130-foot ice slide, an outdoor skating rink, s’mores roasting, and nightly snowfalls.

For this South American country, the whole month of December is full of fiestas. It kicks off with the Alborada festival in Medellin on November 30, when thousands of fireworks light up the night. Then, on Dias de las Velitas (December 7), Colombian families set hundreds of little candles along the streets to light the way for the Virgin Mary. (Trust us, the trip is worth it just to see this glowing affair.) Between December 16 and 24, Colombian families hold one of the most famous traditions: novenas, a string of parties where friends gather to sing carols, recite prayers, and dance all evening. Don't worry if you’re not a local: visitors can still explore some of the outstanding decorations. In Medellín, 31 million bulbs shine throughout the city and in the capital of Bogotá, there is a Ruta de La Navidad (Christmas Route) that features light shows, performers, and Christmas markets in notable areas like Parque Nacional, Plaza de Bolívar, and Parque de los Novios.

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