Flight Time: 2 hours 30 mins | Daily from IAH on Spirit, United, American; Daily from Hobby on Southwest
There are two tickets to paradise: Fly direct to Fort Myers and make the 40-minute drive south, or fly direct to Fort Lauderdale and do the same across the Everglades (double the drive time and the swamp). Either way, you’ll end up on one of Florida’s finest coasts, home to pristine sugar sand, marinas and manses, and (contain yourself) Judge Judy.
On the itinerary? A day trip to the Naples Botanical Garden, naplesgarden.org, where you may develop an orchid habit. Slurp fresh oysters at Captain & Krewe Seafood Market and Raw Bar—these dudes can cook. Or take a fresh catch back to your baller Airbnb (Naples is, in fact, the land of Old Florida dream listings), and prowl bustling, small-town Fifth Street after dark for martini opportunities.
Mostly, though, you’ll want to get some sand underfoot, whether you camp out at Lowdermilk Beach or the Naples Pier, further south at Marco Island (pictured at top), or a ritzy resort in between. Repeated dips in the Gulf are mandatory from daybreak to the sherbet-drip of sunset—do the “stingray shuffle” to avoid mishaps and maybe a manatee will even swim up to say hi.
EAT: Humble strip-mall institution Grouper & Chips has the best conch fritters this side of I-75. grouperandchipsnaples.com
STAY: Go for broke at luxurious, historic Naples Beach Hotel & Golf Club, which boasts 319 rooms with balconies overlooking the Gulf (also: picky kids can opt for the pool). naplesbeachhotel.com
DO: Head to Naples City Dock to hop a charter for a beach day on Keewaydin Island, a sunset cruise, a fishing excursion, or a wildlife tour. naplesgov.com/cdw —Gwendolyn Knapp
SAN JUAN, PUERTO RICO:
Flight Time: 4 hours | Daily from IAH on United; Once daily from Hobby on Southwest
Spend a sunny Caribbean morning wandering the 500-year-old Puerto Rican capital and its centuries-old forts, Castillo San Felipe del Morro and Castillo San Cristóbal—visit both at the San Juan National Historic Site for $10 total, nps.gov/saju—and you’ll still have time to hit popular Condado Beach in the afternoon. At sunset, take a guided LED-lit kayak tour of Condado Lagoon, nightkayak.com, for true Island of Enchantment vibes.—Catherine Wendlandt
Flight Time: 8-9 hours | Once daily from IAH on United; Once daily from Hobby on United
Start by paying respects at the Pearl Harbor National Memorial and taking in the island’s history at Iolani Palace, which was once the Hawaiian monarchy’s official residence and offers daily tours, iolanipalace.org. Seriously, how often do you get to visit a palace in paradise?
You should also spend as much time as you can outside (and don’t forget the sunscreen). Head to mellow Lanikai Beach, 30 minutes north, to escape touristy Waikiki. Trek up the 300,000-year-old volcano at Diamond Head, and if you’re feeling especially adventurous, take a surfing lesson with Ty Gurney Surf School, tygurneysurfschool.com, at Waikiki Beach. The sunset surf package ($550 for two), according to general manager Jasmine Garcia, “has one of the most beautiful views.”—CW
Flight Time: 6-8 hours | Daily from IAH on American, Delta
If someone says they wanna take ya to Aruba, you should say yes. The crystal-clear waters, stellar scuba diving inlets, casinos, volcanoes, fine-dining outposts, and colorful colonial town squares make this constituent country of the Netherlands, just north of the Venezuelan peninsula, a tropical destination unlike any other. It’s nearly a full season’s worth of The Crown in travel time from IAH to the main Queen Beatrix International Airport (how regal!), but American Airlines and Delta offer early-morning flights with stops in Atlanta and Miami, respectively, that will put you at your resort in time to catch the sunset.—Laura Furr Mericas
Flight Time: 5 hours | Daily from IAH on United
You’ll be heading to Baha Mar, bahamar.com, of course. The luxury resort is open for the 2021 season with over 1,000 acres of beach and three hotels to choose from, along with a casino, Jack Nicklaus golf course, flamingo yoga, nine restaurants, and five bars—speaking of which, maybe leave the kids at the on-site Explorer Club day camp.—GK