Pack your swimsuit, a sundress and a few necessities and exchange the dreary Midwest for Hawaiian sun and surf. Oahu's temperatures are perfect for year-round solar worship at Waikiki Beach, an oceanside luau in Honolulu, a hike through a rainforest or an eye-opening visit to Pearl Harbor. With crystal-clear waters and emerald green foliage, winter is a distant memory (808/524-0722; visit-oahu.com).
The islands of Sanibel and Captiva, along Florida's southwest coast, are a beachcomber's dream, covered in glistening maritime trinkets—400-plus varieties of swirly snail shells, delicate pink clamshells, sand dollars and more. You won't find streets lined with high rises, strip malls and fast food here. Instead, enjoy the distinctly mellow Floridian vibe, embraced by locals and visitors alike, all the warm winter long (800/237-6444; FortMyersSanibel.com).
In the Dominican Republic's Punta Cana, palm trees sway in a tropical dance, a breeze caresses your sun-kissed face and white sands sift between your toes. Ahead, the oh-so-blue Caribbean bustles with windsurfers, kayakers and water bikers. With 40 miles of beaches, a vibrant nightlife and an array of all-inclusive resorts, Punta Cana is an enticing—and affordable—winter getaway (809/221-4660; godominicanrepublic.com).
The frigid Midwest melts away in Cancun, leaving your cheeks pink and your soul relaxed. The beaches are unrivalled—white sand contrasting the brilliant blue Caribbean—here, more than 1,000 miles from the northern Mexican border. Swim with the dolphins, brave a salsa lesson or just lie on the beach, hoping your vacation never ends (800/446-3942; cancun.travel).
Snowbirds agree: South Padre island is flockworthy. And it's not just a favorite among Lone Star Staters. Nationwide, South Padre is revered for its warm Gulf waves, boisterous surf culture and unending entertainment—from live music and clubs to kiteboarding, paddleboarding and other surf-related adventures. Leave your winter coat at home. Here, a T-shirt, boardshorts and flip-flops will do just fine (800/767-2373; sopadre.com).
South Padre Island 
Lake Havasu, Arizona, shines with 300 days of sunshine a year, lighting 450 miles of beautiful shoreline. Swim, water-ski and boat across the 45-mile lake, or just laze on the sandy beaches and forget about the snow and ice you left behind. Be sure and check out London Bridge, which was purchased for less than $3 million and transported from England in 1968 (800/242-8278; golakehavasu.com).
At Costa Rica's Manuel Antonio National Park, you get the best of both worlds: A thick rainforest packed with howler monkeys and three-toed sloths behind a picture-perfect beach. December through March is peak tourist season for this white-sand beach, located on Costa Rica's Pacific Coast, and for good reason—it's downright balmy, making for the perfect weather to make like the three-toed sloth and lay around awhile (888/735-0703; visitcostarica.com).