Travel destination: Florida Keys

Best-kept secret

The Florida Keys drift off into the Gulf of Mexico like stepping stones leading you toward exotic locales. Their detachment from the mainland might explain the laid-back, bohemian, sand-between-your-toes vibe that is frankly so different from the rest of the U.S. Driving along the Overseas Highway, gazing over the green Atlantic on one side and the bright-blue Gulf on the other, sometimes only feet away, is magical. It’s up to you to decide where you want to land: quiet, palmtree- strewn Islamorada or vibrant Key West. A few hours from our winter chill, you’ll find yourself paddling in warm sea, sipping umbrella drinks and unable to imagine wearing more than one layer of clothing. It’s equally ideal for a kids’ vacation, and as a romantic getaway.

Climate
In the winter, although daytime temps are usually between 18C and 27C, pack a sweater and a wrap. Occasionally winter fronts stall here and bring nighttime temperatures down to 10C. Summer is hot and humid.

Checking in

The Moorings Village is what Islamorada is all about: hammocks strung between swaying palm trees and white talcum-powder sand lapped by aquamarine waves. The joy here is having your own West Indies–style cottage tucked away on the 18-acre plantation. Every detail has been thought of, from modern kitchens to Wi-Fi, DVDs and beach towels. You can follow your own rhythm, sip a cocktail on the veranda, have movie nights, swim laps in the crystal-clear pool or play tennis — and you’ll rarely see another guest. Housekeeping can be requested and is very reasonable. (Lodging from $275 to $1,500 per night).

With only 16 suites, Casa Morada is the closest thing to a boutique hotel in the Keys: The owners used to work for hip New York hotelier Ian Schrager. The lush landscaping, pool surrounded by a sandy faux beach and complimentary the moorings village Key West yoga classes make this relic from the ’50s a serene, romantic getaway. But don’t expect your all-singing, all-dancing resort; this is simple living in a pared-down, modern style. (Chicretreats.com. Rooms from $199 to $649).

Hawk’s Cay is as close to nirvana as a family resort gets. The Kids, Tweens and Teens programs keep every age group occupied, from two-year-olds to teenagers. Parents, meanwhile, can lounge around the adults-only tranquility pool or disappear off to the spa. The 111 refurbished villas with kitchens, multiple bedrooms and maid service are perfect for families; there’s also a lagoon for kayaking and swimming.(Rooms from $299 to $659).

Key West has become a tourist mecca, but if you want a few days reminiscent of a more literary, Hemingwayesque era, stay at the Gardens Hotel. Once the private estate of an avid plant collector, this gracious, Bahamianstyle inn is set in an acre of orchids and rare trees, steps from Duval Street. (Rooms from $265 to $595).

Fun lunch

Morada Bay is the ultimate funky barefoot lunch spot: Think tables planted in the sand, brightly painted chairs and coloured flags flying in the wind. From grouper ceviche to jerk-chicken subs and artichoke salad, there’s something delicious for all tastes, and you don’t have to rush to get back to the beach because you’re already on it. 

For the perfect fish sandwich, you can’t do better than Key West’s B.O.’s Fish Wagon. An open-air shack with a buzzy vibe, the legendary lunch spot started as a wagon 25 years ago on Duval Street — now it’s been on the Food Network. Have the cracked-conch sandwich: With tiny strips of fried conch and key-lime mayo, it’s simply perfect. 

Dining out

From the giant wraparound verandas to the scattered kilim rugs and Moroccan lights inside, Pierre’s Restaurant feels like a set from Out of Africa. Indeed, it has often been used as a set: You’ll recognize it as the backdrop to J. Crew, Vogue and Ralph Lauren photo shoots. The food is equal to the decor, with thin tempura softshell crab and baked Islamorada dessert (key-lime ice cream under Italian meringue, cooked in the oven). Need we say more? 

If you’re overwhelmed by fish, beat a hasty retreat to Prime 951. Its filet mignon and bone-in rib-eye are so good even Texans come back for more. Dark mahogany walls and martinis create a retro ocean-liner vibe. 

Things to do

1. Who doesn’t love dolphins? Catamaran Echo in Key West has a leisurely four-hour experience interacting with dolphins in their natural habitat. A member of the Florida Keys Wild Dolphin Alliance, it offers respectful, eco-oriented tours that include snorkelling. 

2. John Pennekamp Coral Reef State Park, America’s first marine preserve, is a perfect place to snorkel and dive. There are over 260 species of tropical fish, endless dazzling corals and even the remains of an old Spanish shipwreck to gawp at. If you don’t feel like getting wet, there are glass-bottomed boat tours. Just pack a picnic; you can rent all equipment at the park and even do your scuba certification here.

3. From Key West Seaport, take a ferry to the Dry Tortugas National Park or hop on a seaplane. The park is an old fort complete with cannons, and was a legendary pirates’ lair thanks to its position on the edge of the main shipping channel between the Caribbean, the Gulf and the Atlantic. Kids can become a junior ranger by learning about the natural habitat and history, and leave with a certificate.

Tip: There are no real swimming beaches in the Keys - the sea is shallow and often has bits of rock and coral, so bring water shoes.

Five o'clocktails

There’s no need to put on shoes for the Lorelei. This classic island-style bar sprawls along the sand with swing seats, wooden chairs and a small stage for live music. Sip something cold, dig your toes in the sand and watch for the green flash. 

Locals swear the real Key West is now just over the bridge on Stock Island. Amid the jumble of trailers and fishing boats is the Hogfish Bar and Grill.Sit by the water, watch the shrimpers coming in, drink ice-cold beer and enjoy a view devoid of super-yachts.