Where to Go—and When

The best travels start with curiosity, a desire to go somewhere unfamiliar and do things you’ve never done. But how do you find those offbeat destinations? Where should you go, and more importantly, when?

Winter

Gasparilla Festival — A bit like Mardi Gras with pirate hats, Gasparilla is Tampa, Florida’s best bet for January. Imagine a flotilla of thousands sailing into the bay aboard yachts, barges, and antique galleons. Named for the notorious pirate José Gaspar, it’s been a tradition here since the early 1900s.

There are live concerts, street parades, and mild-to-wild attractions for everyone from coeds to kiddos. So, grab your “mateys” and come ready for revelry, sunshine, and plenty of adult beverages.

Cumberland Island — Cumberland Island National Seashore is a walk in time. This deserted barrier island between Florida and Georgia is accessible only by ferry, which guarantees miles of undisturbed coastline. You’ll kayak through low-country marsh and hike beneath stands of towering oaks. Walk along abandoned beaches and explore the ancient ruins of the Dungeness mansion. Best of all, winter offers perfect seaside weather without mosquitoes or humidity.

If you’re lucky, you’ll score one of 15 guest rooms at the historic Greyfield Inn. Built as a retreat for the Carnegies, it’s the only commercial property on the island. This luxurious home base is the perfect spot for afternoon cocktails, island tours with an expert naturalist, and searching for Cumberland’s most famous residents—a herd of wild horses.

 Spring

Michigan’s Upper Peninsula — Sandwiched between three Great Lakes, the U.P. offers plunging waterfalls, charming towns, and pristine shorelines. Explore Pictured Rocks, one of America’s National Lakeshores, or watch the northern lights trace across an international Dark Sky park. Just don’t miss the ferry to Mackinac Island.

Voted Best Island in America by Travel + Leisure, Mackinac bursts at the seams all summer but is surprisingly uncrowded in spring. Play a game of croquet on the lawn of the Grand Hotel or have a double scoop at the ice cream parlor. Cycle an island that never allows cars or relax on the world’s longest front porch.

Hamilton Pool — A short drive from Austin you’ll come across a creek that drops into a box canyon to create Hamilton Pool. The swimming hole rests inside a cave of gold-colored rocks that curves around to create a natural amphitheater. After a hike down a rocky trail, the path opens up on a magical pool of turquoise water.

While this Texas Hill Country spot is a favorite throughout the year, we recommend early spring when kids are in school and the crowds have yet to descend. Weekdays are best. Just make sure you have advanced reservations since the park limits the number of visitors. Insiders know to always carry cash, wear suitable hiking shoes, and bring lots of water. Afterward, it’ll be time to eat—good thing you’re close to Salt Lick BBQ for what is arguably the best barbecue in the Lone Star State.

Summer

Wakulla Springs — Old Florida comes alive at Edward Ball Wakulla Springs State Park in an iconic 1930s lodge made famous in black and white movies. It’s a return to the early days of travel when folks still dressed for dinner, white linens set the table, and Big Band music filled the night.

There’s a soda fountain with cherry phosphates and the nation’s largest spring-fed swimming hole. Look out for manatees and alligators on the Jungle Cruise or watch for chimney swifts that shelter in ancient cypress trees.

Cumberland Caverns — At the end of Dark Hollow Road in McMinnville, Tennessee, lies the entrance to Cumberland Caverns. Hidden some 333 feet below the surface, there are miles of passageways for climbing and spelunking. Squeeze through tight crevices and ascend high climbs in Higginbotham’s Hollow, or scale the canyons of Devil’s Quarry. If you’re up for a real adventure, try the Guts and Glory route across the steepest parts of the cave.

The cave’s most unforgettable feature is a concert hall known as the Volcano Room. A giant chandelier hangs from the rock and craggy outcroppings serve as the stage. Musicians love this venue that owes its exceptional sound to the uneven surfaces that scatter the sound waves. Just remember to bring your jacket for the year-round chilly temps.

Fall

Broadway in NYC — Foodies have Restaurant Week. Shoppers have Black Friday. For theater-lovers there’s Broadway Week. It happens twice a year, including a week in early fall. This is your chance to steal BOGO deals to most of the season’s best-loved shows and musicals.

In addition to Broadway bargains, autumn means fewer crowds, amazing weather, and Central Park draped all in fall foliage. Head to the top of the Met for treetop views of the fiery landscape or toward Union Square Greenmarket for just-picked Hudson Valley apples. Stroll along The High Line on a cool afternoon or join The Feast of San Gennaro in Little Italy. Plus, if the stars align you may get the chance to enjoy Fashion Week at the same time!

Louisiana’s Cajun Bayou — Just up the road from New Orleans, Lafourche Parish is ground zero for Cajun cooking and Acadian culture. From spicy boudin and sloppy po’boys to crispy cracklin and crawfish boils, it’s the intersection where flavor and tradition meet.

Drive through wetlands on an autumn day, when the humidity drops and the roads are empty. Snake your way past weekend produce stalls and old-fashioned meat markets. Throw back a craft cocktail or pile your plate high with farm-to-table recipes. Afterward, book an airboat swamp tour, kick up your heels with some zesty zydeco, or discover fall festivals celebrating everything from music to gumbo.

Where, When, and Next—More Destinations to Consider

An Old-Fashioned Christmas in Dahlonega, Georgia

Spring Trail Riding on Daufuskie Island, South Carolina

Summer Rafting at River Ranch Lodge in Tahoe City, California

The Fall Art Scene in Bentonville, Arkansas