Founded in 1888 as a haven for families like the Rockefellers and Vanderbilts, Jekyll Island Club Resort's Victorian-style clubhouse evokes its Gilded Age glory. Elegant balcony rooms overlook 9 miles of private beach. Sunbathers have options: The resort's two pools or the Jekyll Ocean Club, with complimentary beach chairs and umbrellas. Feeling competitive? Try your hand on the croquet lawn.

Off Property Walk the Wanderer Memory Trail, which commemorates more than 400 Africans aboard one of the last known slave ships to arrive in the United States.

Perched on a private natural sand beach, The Reach Key West, Curio Collection by Hilton offers a tropical escape with a boutique feel (and a postcard-worthy pier). Book experiences with locals like Barefoot Billy, who guides an epic, 26-mile Jet Ski tour, or Marianne van den Broek, a professional sand sculptor who leads workshops. And pack your sweet tooth: The resort's Four Marlins restaurant serves one of the smoothest slices of Key lime pie on the island. The chef's secret? Fresh-juiced limes and candied ginge rin the crust.

Off Property See the homes and haunts of Ernest Hemingway, Shel Silverstein, Robert Frost and others on an Old Town Literary Walking Tour.

Don't startle and spill your Mobile Bay Sunset (a specialty poolside cocktail) when you hear a cannon firing at Grand Hotel Golf Resort. It's a daily tradition dating to 1847, when guests arrived via steamboat. (Later, the property served as a makeshift military hospital during the Civil War.) A member of the Historic Hotels of America program, the resort has been wonderfully preserved, yet is a modern playground for adults and kids alike. Fill your days with golf, tennis and spa visits, or play croquet on two championship lawns that debuted last fall. 

Off Property Explore Fairhope, a charming bayside town with boutiques, bookshops, antiques stores and streets lined with live oaks. 

Decades seem to dissolve when you sashay along Peacock Alley, the grand promenade through this 112-year-old (and very pink) property. A massive recent renovation transformed the former Hotel Galvez into a Gatsby-esque vision, with harlequin black-and-white marble flooring, brass banisters, crystal chandeliers, and pink-and-white-striped pool cabanas. As the only historic hotel along the Texas Gulf Coast, Grand Galvez leans into its lore with regular tours recounting paranormal activities. 

Off Property At Galveston's Historic Seaport, visit Ship to Shore, a series of interactive rooms chronicling survival stories of the area's first immigrants in the 1880s.

Drive across the Boca Grande Causeway, about an hour from Fort Myers, and ease into a glamorous old-Florida vibe. Gasparilla Island's one and only resort opened in 1913 and remains family-owned. Book one of the balcony suites that have hosted Katharine Hepburn, Henry Ford and Thomas Edison, or let waves lull you to sleep inside one of the larger beach cottages. Don't miss the famously grand breakfast spread (brioche French toast! Lobster omelets!) at The Inn's Dining Room.

Off Property Rent a Gasparilla Adventures electric golf cart to traverse the island on four wheels and head to dinner without worrying about parking.

A half-hour from downtown Charleston, this expansive family-friendly property encompasses 1,600 acres of oceanfront, multiple restaurants, two golf courses, pickleball and tennis courts, and more pools than you can count. Choose from plush rooms at the new Sweetgrass Inn or full-size homes for larger groups. Beach hair? Don't care, with activities like marsh kayaking, ocean fishing, boat tours and sweetgrass basket-weaving classes. 

Off Property Catch a concert at The Windjammer in Isle of Palms, a one-of-a-kind beach venue with live music from local bands and big-name artists.

Related: A Sweetgrass- and Soul Food-Filled Winter Getaway to Charleston