This is the straightest road I’ve been on for a while, and I’m from the Prairie. We’re bombing down Florida Highway #1 heading south. In a few minutes, we’ll be on the famous Overseas Highway of the Florida Keys, the longest overwater road in the world, with 42 bridges, including one that is 11 kilometres long. This Florida Keys road trip is an adventure I’ve been looking forward to ever since watching the chase scene in True Lies, where Jamie Lee Curtis holds onto the helicopter skid for dear life. More than two million people visit the Keys each year. That’s a lot of convertible Mustangs.

Duck into a roadhouse. These iconic eateries line the highway, some quirky, some plain—all delicious. At The Fish House, we slide into the start of what becomes a week-long routine, selecting a fish—grouper, yellowtail snapper, mahi mahi, and more—then choosing how we’d like it prepared—grilled, blackened, breaded, pan sautéed, jerk, the list goes on. The Keys restaurants have menu staples that quickly become a good habit: conch chowder, spicy tuna nachos, lobster done every which way, stone crab claws, crab cakes, fried oysters and of course, variations on the celebrated Key Lime Pie. Open-air places like Sundowners and Keys Fisheries sport large wooden terraces filled with locals and tourists alike, inhaling right-off-the-boat fish along with decent local craft beer.

Escape into the sea. If you are in any way watersports-inclined, the tiny History of Diving Museum is a gold mine of stuff relating to the underwater world, fun even if you’re not a diver. The collections of helmets and masks is beyond good, as is the exhibit on the history of underwater photography.

Feed the tarpon. At Robbie’s Marina in Islamorada, tourists hand-feed the giant tarpon that favour the pier here. We sink into stools on the deck of the adjacent, aptly named Hungry Tarpon restaurant, order Trailer Trash Bloody Marys and fish burgers, then watch the big pelicans bite the children. One even drew blood. So fun.

Feed the turtles. The tour of The Turtle Hospital in Marathon is well worth a visit. This non-profit rescue-rehab-release facility is the only hospital dedicated to endangered sea turtles in the world. The patients suffer mostly from accidents with boats and from a disease that gives them tumors. Turtles that can’t be released because they would never survive live in what was once a giant swimming pool. You can throw them pellets.

Rest in Key West. We find a comfortable, devil-may-care attitude here spilling into all the different parts of the culture. This two-by-four-mile island was originally an eclectic haven for Native Americans, Spaniards, freed slaves, sailors and pirates, eventually welcoming the creatives, the queers and the misfits. You’ll fit right in. I sure did.

THINGS TO DO: VISIT THE BUTTERFLIES

When you go. The best time to visit The Florida Keys is between March and May, when the volume of tourists and nightly rates are down. Check out fla-keys.com and visitflorida.com to plan your trip.

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Vibe: Most Ocean Key guests have visited before and wouldn’t stay anywhere else. While not exactly high-rollers, they have a certain air of success about them, particularly the groups of vacationing middle-age couples and young families. Keep an ear out for Alabama and Georgia accents—perfect for a game of spot the American.

Rooms: A natural Caribbean look—a turquoise, green, blue and yellow colour palette, hand-painted furnishings and local art—sets a relaxing and breezy tone. Speaking of breeze, all rooms feature a private balcony with views of the sea or Duval Street. Along with a pull-out sofa and jetted tub, you can expect a minibar, free Wi-Fi and in-room dining. Two-bedroom suites size up to 1,200 square feet, the largest on the island.

F&B: You can eat at the pool and on the Pier—savouring ceviche, conch hushpuppies and fish burgers—but save your belly for Hot Tin Roof, named after author Tennessee Williams, who spent a lot of time in Key West. Find painted ceilings, teak and mahogany trim, white leather chairs, warm ocean breezes and quiet company. Tuck into Caribbean and Floridian comfort food like scallop risotto, caramelized grouper and broiled lobster.

Extras: The guests-only pool is really kind of a pool-slash-lounge, all striped blue drapes and white cabana beds, frozen fruit treats and proper terry chaise covers. Sunset Pier along the sea side of the property offers not only the best place to catch the sunset, but also a local live band every night. And don’t worry, there’s lots of shade there if you’ve taken to day-drinking. Spa Terre is small, but its island-themed treatments, particularly the facials, will set you up with prime pampering.

Off-Site: Happily, Mallory Square and all the busking, trolley-bussing, and tourist-attracting charm is right outside and around the corner. Enjoy the whole of Old Town’s shopping, dining, museums and attractions all within an easy one-square-mile pedi-cab ride. The Key West airport is a 20-minute drive away.

Rate: $$$

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