In my early Floridays, a road trip to the Keys meant one thing: Party! We’d find a cheap roadside motel or throw together some camping gear and dive equipment and head down to the legendary Overseas Highway.
So in addition to “party,” “cheap” was the operative word back then, and the Keys obliged with inexpensive dives (that had nothing to do with going underwater), two-buck T-shirts and 99-cent breakfasts.
Today, though, the Keys have matured, and so have I — well, at least my taste in travel has. Okay, I still equate “party” with the Keys. But these days I’m looking for a little pamper and posh with my Keys adventure. I love to land in Key West and work my way up through the pearl-string keys — preferably in a rented Jaguar XK or Lamborghini Gallardo Spyder convertible that I can reserve in advance and pick up at the airport.
AT MILE MARKER 0
Never miss a local story.
Key West is known for its unabashedly raucous party scene. For an alternative to the Duval Crawl along Old Town’s most infamous thoroughfare, slip into d’vine Wine Gallery on the lush grounds of the Gardens Hotel. It hosts regularly scheduled wine-tasting classes, but for the ultimate, arrange ahead of time for a private sipping session customized to your preferences in wine — a pinot noir tasting, perhaps.
Or arrange an intimate cocktail party in the grand, historic setting where President Harry Truman once entertained — The Truman Little White House.
The Key West Butterfly and Nature Conservatory can arrange after-hours Twilight Tours with champagne and a curated tour of its sophisticated brand of art with wings.
Upgrade your Duval Crawl by haunting the galleries at the south end of the street. Pre-arrange a behind-the-scenes tour of the gallery and studio of Alan S. Maltz, the official wildlife photographer of the State of Florida. From the photographer himself and his production team, learn camera-to-canvas techniques and take home one of his stunning prints and two coffee-table books of his images — just $1,550 for two.
The Keys are all about getting out on and into the water, and Key West is no exception. Any number of private charters can take you fishing, snorkeling, diving and sightseeing, but a few stand out for their exclusivity.
The snorkeling at Garden Key in the Dry Tortugas weighs in at the superlative end of the scale. You can make the day trip in 40 minutes with Key West Seaplane and beat the crowd that arrives later by fast ferry.
You’ll see sea turtles, dolphins, shark, rays and shipwrecks from the plane, and lots of vibrant fish while snorkeling. For a closer encounter with dolphins, Dancing Dolphin Spirits Charters on Stock Island takes small groups and private tours into the uncharted backwaters of Key West to commune with dolphins — or do yoga, find birds, whatever your passion. Capt. Victoria Impallomeni customizes each tour.
For the ultimate dolphin experience, swim like a dolphin with a tow behind the boat on a special dolphin board that simulates the animal’s motions.
Come sunset, eschew the throngs at Mallory Square and celebrate day’s end on a double-masted Appledore schooner sail with Sebago Key West. Whether it’s you and your significant other or a group of friends or family, the charter outfit can arrange champagne, gourmet dining, and even live music for your private sail into the sunset. Photogenic against the dusk backdrop, the ships are equally gorgeous and plush on the inside, with spacious seating areas and room to roam on deck.
When it comes to dining landside, Key West has no shortage of restaurants, divine to divinely funky.
For breakfast, if the lobster benedict with Key lime hollandaise at Blue Heaven isn’t decadent enough, try the Key lime pie-stuffed French toast or prime rib hash with truffle hollandaise at Azur Restaurant.
Louie’s Backyard serves creative fare as delicious as its sea views for lunch or dinner. My favorite for dinner deluxe resides conveniently next to the elegant Marquesa Hotel. Intimate and white-linened, Marquesa Café tempts with the likes of sweetcorn-dusted diver sea scallops with smoky pepper butter.
Key West excels in privileged accommodations with historic patina — from its plethora of Victorian-style B&Bs to the flapper-era Casa Marina that will make you feel like you’re walking onto a set of The Great Gatsby.
Book an Ocean Vista Suite with a loft and all the luxuries. Take playing in the sand a step up by reserving a private sand-sculpting class and creating your own masterpiece. For an added dose of pampered romance, you can book a Toes in the Sand dinner on a private beach.
For the ultimate steal-away luxury in Key West, take the short ferry ride to the cushy cottages of tranquil, romantic Sunset Key. Appointed in tasteful nautical motif, the cottages feature full kitchen facilities and range from one to four bedrooms. All three bedrooms in the oceanfront cottages have stunning views. Service is impeccable, including the delivery of fresh breakfast goodies to your door every morning and your own customized spa product with treatments.
HIT THE ROAD
After Key West, you’ll want to make some stops for Lower Keys flavor.
Nowhere does it taste as sweet and privileged as at Little Palm Island, a South Seas-style private island resort with romantic mosquito-net-draped beds, al fresco showers, rich spa treatments and waterfront dining. Do not expect telephones or TVs, however, at this resort, where rates start at $890 in low season.
If you can’t spend the night, make reservations for lunch or dinner. (Call in advance for a private torch-lit beach dining table.) It’s an easy, relaxed way to sight the Key deer that the Lower Keys are famous for while relishing lively gourmet cuisine with a Latin-Caribbean accent. Don’t skip the Key lime pie. Many claim so, but it truly is the best I’ve tasted.
Up the road near Marathon, sign up for the one-on-one Trainer for a Day interaction program at Dolphin Research Center — price: $675.
IDLING IN ISLAMORADA
Grand art and sport fishing have attracted presidents and celebrities to Islamorada since Zane Grey and before.
Early on, they stayed at Cheeca Lodge, still a top dog with its luxury rooms, redesigned after a fire wiped out much of the main lodge a couple of years back. Mine, on a recent stay, came with a circular outdoor soaking tub that filled from a stream coming out of the ceiling — the final elegant touch to spacious accommodations with plush furnishings and a dreamy marble bathroom.
You can hardly leave the “Sport Fishing Capital of the World” without casting a line, so ask Cheeca Lodge staff about its half-day offshore or backcountry fishing package. Or contact VIP Fishing Charters for premium gear and a smooth, comfortable ride that accommodates up to six, with rates starting at $700.
For more intimate accommodations and a prettier beach, book a one-, two- or three-bedroom cottage at the Moorings Village next door to Cheeca. You will find lots of privacy in the well-spaced cottages, deluxe kitchens, teak lounge chairs for gazing seaward from the porch, a lap pool and spa pampering.
Plan on dinner at Chef Michael’s, where the kitchen puts an exquisite spin on local seafood. Or, for over-the-top extravagance, call for a catered dinner delivered to the balcony or porch of your waterfront accommodations.
KEY IT UP IN KEY LARGO
Key Largo’s diving reputation rivals Islamorada’s fishing chops, with countless diving operations to get you some bottom time. You can even sleep underwater in your private chamber at Jules’ Undersea Lodge.
For a different kind of exclusive stay, intimate Kona Kai boasts its own botanical gardens and fine art gallery. Here, each of the 13 designer rooms has a distinct personality — a sophisticated version of Keys cottage style decorated with fresh garden flora and original art and supplied with deluxe amenities such as Wolfgang Puck coffee. Bright and cheerful, the Breadfruit Suite opens onto the beach with striking views of Florida Bay. Ask for a beach massage or private yoga class.
Experience the sea side of Key Largo’s personality on a sightseeing tour. The African Queen — yes, that African Queen — takes you on a singular journey back to Hepburn, Bogart and steam-driven wood boats. Private tours steer through Key Largo’s canals to dinner at the Pilot House, something of a local secret tucked off the main Overseas Highway.
Key Largo restaurants spur a salty flavor, one of the most famous being the Fish House. Its slightly upgraded next-door sister restaurant, Fish House Encore, adds a sushi bar and live music to the character. Try the fish Matecumbe (featured on the Food Network) for the freshest in seafood or the elegant crown rack of lamb if the meat mood strikes.
For the final sweet touch to your luxury road trip, just add chocolate. Key Largo Chocolates can arrange a chocolate-and-wine experience where you learn to make decadent truffles and chocolate dessert boxes to take home while sampling fine wines and the best Belgian chocolates.