7 Merry Cities to Spend Christmas

From Boston’s cobblestoned streets to Taos’ paper lanterns, these are the country’s most festive cities

Whether you’re getting away from your family or visiting your relatives, Christmas travel is all about finding that warm and fuzzy feeling of snuggling by a fireplace, listening to carols, and exchanging carefully considered gifts. But not all destinations are created equal when it comes to twinkling lights, sweet shop windows, and the general jolly spirit of the season. Some cities really come into their own around the holidays, with festive details big and small that visitors and locals savor.

 

Boston

The historic cobblestoned streets and heaps of New England charm play in Boston’s favor over the holiday season. Holiday markets sell local artisans’ works; restaurants with cozy fireplaces serve classic, hearty roasts (or roasted lobster) and holiday dinners; and families can warm up with hot chocolate after ice-skating on Frog Pond.

Stay: XV Beacon is one of Boston’s most modern and charming boutique hotels and it puts you within steps of the classic cobblestoned streets of Beacon Hill, where cute cafés are only outnumbered by local boutiques. 

Eat: Spend Christmas Eve at the sleek Bistro du Midi, indulging in a Provençal menu of Christmas-inspired dishes.

Play: Skating on Boston Common’s Frog Pond is fabulous Boston fun, take the kids to Boston Ballet’s production of "The Nutcracker," or join in the candlelit carol singing at Trinity Church.

Chicago

From the Christmas tree in Daley Plaza to the brightly lit and wildly decorated holiday train, Chicagoans play on all aspects of the Christmas spirit. The lights on the Magnificent Mile, snowy trips for pretzels and hot mulled wine at the city’s huge Christmas market, and ice-skating in Millenium Park make for high-energy holiday activities. (Photo courtesy of Flickr/Marit & Toomas Hinnosaar)

Stay: The Sax Chicago, right on the Chicago River, has a fun and whimsical design, with romantic touches and bold colors throughout. The hotel’s restaurant, Bin 36, is a chic and relaxed watering hole that serves as breakfast spot, wine and cheese bar, and cocktail lounge.

Eat: Sink into a red leather armchair and settle in for your Christmas steak at Drake Bros in the Drake Hotel.

Play: Bring the kids to Navy Pier’s Winter WonderFest, complete with rides, a huge Christmas tree, and live music, and stare out at the giant tree while last-minute shopping at Macy’s.

Park City, Utah

Find the ultimate white Christmas in Park City, Utah, where Main Street looks out onto snowcapped mountains and days are spent skiing the slopes. Stroll down Main Street, popping into little boutiques, and join the annual Torchlight Parade on Christmas Eve.

Stay: Spring for a luxe holiday getaway at the Montage Deer Valley, where your hardest decisions will be whether to ski or après-ski.

Eat: Sneak into a cozy table at Canyons Resort’s Alpine House for comforting holiday fare and a long list of wines, like robust reds that pair well with the snowy mountain outside.  

Play: Zip up that red velour suit, because every December the city hosts a Santas Ski Free day. Or watch as a lone (hired) Santa Claus skis the slopes himself before delivering treats to kids.

 

San Juan, Puerto Rico

Before anyone cries foul that it’s not technically in the United States, you don’t need a passport to get there and they really do it up on Christmas. Plus, it’s sunny, so quit whining. Join carol singers, experience a traditional midnight mass, snap up unique wooden crafts made by local artisans, and enjoy classic Christmas dishes like pasteles and roasted suckling pig.

Stay: Rest your head in the Old World-style El Convento hotel, where ocean breezes waft through open balconies in bright and airy rooms. 

Eat: Stick to holiday classics at Ajili-Mojili, where everything from arroz con gandules to roasted suckling pig are on offer, with flan and arroz con dulce to finish off the meal.

Play: Listen to a salsa-style version of "Jingle Bells," attend a midnight mass, and go wild with locals on Christmas Eve (called Nochebuena) where traditional feasts are served and eggnog is replaced by a type of coconut nog.

Charleston, S.C.

Few places boast the same kind of romance and sense of tradition as Charleston, S.C., the city that manages to always feel like a small town. There’s also no better place to have a truly Southern and boozy Christmas than Charleston — eggnog is spiked with bourbon and the traditional St. Cecila Punch is still served today (it originated at formal Christmas balls in the 1700s). Sleigh rides, tea parties, twinkling lights along small side streets, and a giant Christmas tree round out the spirit of the season. (Photo courtesy of Charleston Place/Joe Vaughn)

Sleep: Book a room at the grand and quintessentially Southern Charleston Place, where you can escape the cold with hot chocolate in the Palmetto Café or a swim in the spa’s pool.  

Eat: Find lowcountry classics like She Crab soup, heirloom grits, and short ribs at Poogan’s Porch.

Play: Listen to carol singers at Drayton Hall Plantation and take the kids on a sleigh ride, or leave the little ones at home and join the annual Holiday Pub Crawl.

Taos, N.M.

For most non-desert-dwellers, the thought of spending Christmas in Taos may come off a bit strange, but this small New Mexican city is incredibly festive and beautiful this time of year. The streets are lit with paper lanterns, skiers savor the Taos Ski Resort, and Christmas traditions are mixed with American Indian rituals, making for a completely unique Christmastime.

Sleep: Book into a rustic casita at Casa Gallina. An ex-New Yorker escaped to New Mexico to open this cozy and gorgeously decorated small inn with animals running around and great homemade food coming from the kitchen.

Eat: Dine on comforting foods made with locally sourced ingredients at El Monte Sagrado hotel’s De La Tierra.

Play: Take the kids to a three-story Native American puebla in town, stroll along the “luminarias” (paper lanterns) lit up along the streets, and watch the Yuletide parade.

New York City

Of course, New York City is the ultimate classic Christmastime destination, where everything from department store windows to giant Christmas trees are iconic staples of the holiday spirit. Skating in Central Park, munching on roasted chestnuts washed down with piping hot chocolate, watching the legendary Rockettes, strolling down Fifth Avenue with snow coming down — it’s the romance of Christmas all in one place. (Photo courtesy of Flickr/Vibragiel)

Sleep: The Waldorf Astoria is a New York City classic, while 6 Columbus is a sleeker, boutique option, and the Andaz Hotel puts you right next to the ice-skating rink at Bryant Park.

Eat: Right off Fifth Avenue, Brasserie 8 ½ will serve a classic French Christmas Day meal, or saunter into the Sea Grill for an up-close view of skaters on the Rockefeller Center rink.

Play: Ice-skating at Rockefeller Center, Bryant Park, or in Central Park is a must, as is window shopping (or real shopping) at the beautiful boutiques and department stores on Fifth Avenue, and staring in awe at the city’s enormous Christmas trees.

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