The South's Best Towns for the Holidays

The holiday season coincides with the kickoff of high season in this northwest Florida town, which also ranked well for beach vacations, family getaways, and boutiques. So it’s a good place to browse for notable gifts, from the heirloom-quality porcelain at Santa Rosa Pottery to the pre–World War I cookbooks at Kitchen Garden Books & Antiques. Folks who don’t want to put on holiday pounds might consider the 40-mile Winter Solstice Run, which begins in Santa Rosa at dawn on December 19, 2015, and goes along beaches, lakes, and through state forests (good news: there are also shorter versions and a relay). Luckily, the town also boasts year-round running weather.

Winter weather doesn’t really kick in until January in this Outer Banks town, so the holiday season is typically still a good time to paddle a kayak or take a boat tour along Taylor’s Creek. The Christmas lights take to the water too: one of the biggest holiday events is the Crystal Coast Christmas Flotilla, a twinkling-lights-strewn boat parade held on the first weekend in December. Readers’ favorite cuisine in this low-key town are the sandwiches: try the double crab cake Cranky Crab at the Beaufort Grocery.

This Florida town lacks snowman-building material, but the snowbird-style winter wonderland still lures holiday revelers with its luxury stores, cool boutiques, and festive ambience. Third Street South is the headquarters for the official tree, evening “snow” showers during Thanksgiving week, and gorgeous window displays, like those at department store Marissa Collections in the Old Naples Historic District. Continue shopping along Fifth Avenue South, and check out whimsical clothing and gift shop Wind in the Willows, whose window won Best in Show at the 2013 local holiday decorating contest. Of course, the holidays are about more than retail; catch the Naples edition of the worldwide TUBA Christmas, a concert on Fifth Avenue South’s Sugden Plaza featuring brass tubas, euphoniums, and baritones.

This military town along the Chesapeake Bay does plenty of pomp, circumstance, and tailgating during the holiday season. Annapolis ranked well for Christmas lights, notably the drive-through Lights on the Bay in Sandy Point State Park, which starts up in mid-November. Downtown Annapolis also keeps its shops lit and open until midnight on a few Thursdays during December. To celebrate alongside the military locals, you can hear Handel’s Messiah performed by the Naval Academy Glee Club in the Naval Academy Chapel, or just sit tight until the Military Bowl, which comes every yaer in late December, at the U.S. Navy–Marine Corps Memorial Stadium. No surprise, the locals also scored well for being passionate sports fans.

During the holiday season, Charlottesville quiets down, as college students cram for finals and then head home. Any visitors get the perk of experiencing the Holiday Evening Tours of Jefferson’s Monticello. Charlottesville scores points for its cool, gift-friendly bookstores like downtown’s New Dominion Bookshop, the oldest indie bookstore in the state, and the used-book gold mine Read It Again, Sam. Readers also rated the town well for its local wineries; King Family Vineyards sells gift-wrapped bottles of Cabernet Franc.

History-rich Williamsburg, where tricornered hats count as timeless fashion, scored highly for colorful people-watching. This time of year also offers plenty of events that let you experience a holiday season like the colonists would: in Jamestown you can watch as wild turkeys are roasted and puddings are prepared, and see how settlers may have observed Christmas (including a few long-gone English traditions like an anti-Santa called Lord of Misrule). Readers’ favorite meal around here was brunch: try the Virginia ham and biscuits, with the Special Rebel Cocktail (tomato juice, beer, and spices), at the Old Chickahominy House.

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Late fall and early winter are a good time to score lower rates in this family-friendly town, but that doesn’t mean that the place has gone totally quiet. Showstoppers around Myrtle Beach include the twinkling Christmas trees and 5,500 hand-lit candles at Brookgreen Gardens as well as the Festival of Trees—with themed trees for all 50 states—at Ripley’s Aquarium. Readers had a weakness for Carolina barbecue in this classic-boardwalk beach town: you can stay true to the season by ordering barbecued turkey at Waterscapes, in the Marina Inn at Grande Dunes, where the bird is lovingly slathered with the mustard-accented, South Carolina–style sauce.

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Grande dame hotel The Greenbrier is the epicenter of the holidays in the Lewisburg area. The 18th-century resort trims the lobby with opulent decorations, holds ribbon-tying seminars in its Christmas Shop, and offers weekday discounts on treatments at its legendary mineral-springs spa. While you can hear the West Virginia Symphony play at Lewisburg’s own Carnegie Hall, the town may otherwise win the Silent Night award, getting high marks for peace and quiet.

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