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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Tucked away near the bottom of Miami’s fabled Ocean Drive, past the pastel-painted strip of Art Deco hotels and their raucous sidewalk eateries, sits SoFi, the soothing South Beach neighbourhood south of 5th Street. Here, a quaint and quiet combo of condos and small resorts delivers a peaceful beach vibe, one that’s happily echoed by the Marriott Stanton South Beach.

Vibe: A retro cottage feel greets you in the lobby: tons of blonde wood punctuated by colourful, quirky artwork, low-slung leather sofas, terrazzo flooring, mid-century-style wooden sideboards propping up cool lamps.

Rooms: The beach cottage character continues up in the rooms, with their creamy white walls, even more wood and herringbone-patterned ceramic floors. A leather headboard, curved work station, velvet arm chair and ample bathroom complete this comfort zone. Everything is modern and airy, right down to the little vermilion chairs on the balcony.

F&B: Tuck into the carnitas, then a platter of ribs with grilled spring onions and fresh avocado at Lolo’s Surf Cantina, the Stanton’s Baja-inspired parkside café, where the mezcal margaritas have me at “hola.” Sure I could live here, but I’d have to get bigger pants. This certainty is underlined later on at Azabu Miami Beach, the resort’s Zen, izakaya-style restaurant, complete with a wall of Japanese whisky.

Extras: Spend the extra dollars for a value-added package that nets you faster internet, welcome margaritas, free bottles of water, beach chairs, bike rentals and one fitness class per day—things like cardio kickboxing, high intensity interval training and mat Pilates.

Off-Site: The fact that SoFi is within walking distance of a lot of good food—dozens of restaurants and bars, including the iconic News Cafe, the legendary Joe’s Stone Crab, celebrity chef Justin Smillie’s Upmarket and more—gives the Stanton an even greater edge.

Rate: $$

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Vibe: This is a fairly moneyed, pineapple mojito kind of crowd, but laid-back enough to enjoy the boho-tinged vibe. At sundown, an Eventide ritual gathers guests together for shoreline cocktails and music by the fire pits, some right from the pool, some already dressed for dinner.

Rooms: The 177 modern-traditional rooms, suites and bungalows are comfortable and luxurious, featuring natural colours and dark wood, tufted chairs and headboards, plus a few nautical touches to remind you that you’re actually at the beach. Amenities include a mini-fridge, iPad, free Wi-Fi and premium cable.

F&B: The open-air oceanfront restaurant Sol by the Sea has a beach house flavour, all driftwood décor with brightly coloured accents. The great views of the bay set you up for American coastal cuisine, things like crab fries and curried black grouper—and pineapple bread with molasses butter. Lobby bar Las Olas features Peruvian style ceviche, washed down of course with Pisco Sours. Steaks and seafood can be found at the fine-dining venue La Marea.

Extras: Ocean Spa and Lounge is spacious and modern, combining modern cosmetic tech with tropical wellness wonderment. Watersports include all the paddles, personal watercraft, parasailing, eco tours and private charters. Triple hammocks are strung out on triangular metal frames so as to give the poor trees a break.

Off-Site: The Playa Largo is 65 miles from Miami airport and 100 miles from Key West, so almost halfway down the Overseas Highway. Watersports like diving and reef snorkelling are close at hand, with glass-bottom boat tours and kayaking to be found in nearby John Pennekamp Coral Reef State Park, just five miles away.

Rate: $$$

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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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Vibe: There’s an international crowd at the Eden Roc, fairly well-heeled, and relatively young. Because of the two hotels in one layout, you see all kinds—the scenesters checking into the Nobu and the business creatives and laid-back leisure crowd signing up for the Eden Roc’s cool brand of sophisticated swing: Frank Sinatra, Elizabeth Taylor, Nat King Cole—the hotel is steeped in entertainment history.

Rooms: There are two towers here, one from 1956 and the other built in 2006, both offering high-style Miami luxury. The older suites are small but chic, with sky-blue patterned carpeting and tall, white headboards; dark, minimal furniture. The new tower sports the same simplicity with each room having an ocean view. Find neutral tones and lighter wood here, with big TVs, a desk, a garment steamer (so handy and it worked!), a Bluetooth speaker, rainfall shower heads, a lighted mirror, a gourmet coffee machine and boxer-style bathrobes.

ROAD TRIP: THE FLORIDA KEYS

F&B: In 2016, the Eden Roc passed the management of its food and beverage facilities to Nobu Hospitality. The circular lobby lounge is an Art Deco dream, busy day and night, with still a bit of a scene after dark, even after all these years. Off the lobby, Nobu Restaurant still defines dramatic Japanese style and cuisine, mouthwatering if more than a little pricey. Poolside, Splash by Malibu Farms serves healthy organic fare throughout the day, including an à la carte breakfast.

Extras: Wind up or down at either the massive gym or the destination day spa, replete with steam room, sauna and hot tub. Borrow one of the hotel bikes for free and go for a spin along the boardwalk, rent a cabana poolside, or stretch out for full service at the beach.

Off-Site: Perfect spot, really: A 10-minute drive to Lincoln Road and the “city centre,” Lummus Park and the historic Art Deco District, and a 20-minute drive to downtown Miami, the Wynwood art district. The luxury shops of Bal Harbour are 20 minutes north. Miami International is 30 minutes away.

Rate: $$$

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The Eden Roc
Well, this one is actually in Miami Beach proper. The terrazzo floors of the sunken lobby bar at the Eden Roc have welcomed the footsteps of Frank Sinatra, Katharine Hepburn and Nat King Cole, who sang “Unforgettable” for the first time in what is now the Mona Lisa Ballroom. Elizabeth Taylor used to circle the bar, carrying on out the door if she didn’t see anybody worth hanging out with. EdenRocMiami.com

Soho Beach House
While the Soho is a member’s-only club/hotel, the main-floor courtyard houses Cecconi’s Miami Beach restaurant, which is open to all. The bar is long, lean and comfortable: Green and white tile floors, tufted sofas, fairy lights in the trees. The incredible Sunday brunch spread takes over the whole lobby: salmon tartare made to order, whole grilled mahi mahi, flatbread pizza with Parma ham, bottomless drinks if you’re up for that. CecconisMiamiBeach.com

The Standard
The Lido Restaurant and Bayside Grill is a true local hangout, the name a homage to the hotel’s original name: Lido Spa Hotel. Thirsty regulars congregate beside the pool at the low four-tops or along little banquettes built around flat-leaved sea grape trees. Gorgeous servers keep Ketel One martinis coming as fast as you can throw them back. This is one of the city’s most beautiful spots for a nightcap at the water’s edge. StandardHotels.com/Spa-Miami-Beach

The Metropolitan
The Met’s Traymore Bar, propping up a restaurant of the same name, manages to be both modern and nostalgic for the old Miami spirit. The bar’s claim to fame is its dedication to gin: They stock more than 30 artisanal varieties. Original pink and pistachio flooring is offset with white scalloped drop-ceilings, white walls and white rattan chairs. The whole place smells heavenly of the hotel’s eucalyptus and geranium signature scent. ComoHotels.com/MetropolitanMiamiBeach

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