Two very welcoming luxury resorts in the Florida Keys—one situated off Marathon, the other edging Key West—amongst the area’s newest offerings, are transfusing new blood into that sepia-postcard of a 180-mile-long escape hatch along the Overseas Highway, which rolls over countless bridges from Miami to the Southernmost Point of the United States.
You’ve got the Atlantic on the one side, the Gulf on the other, and you just follow the salt-encrusted mile markers to marina bars, key-lime pie stands, shell shops, literary landmarks, turtle hospitals, and a flotsam of stilt-house, fried-fish-and-margarita joints between. Keep your eyes on the road. It’s one of the world’s most scenic routes, and there’s passing dolphin pods and blurry-eyed snowbirds coming and going. For the epic drive we rented something suitably cool via Turo—more on that below.
Eventually you’ll arrive in Key West, an exotic time bubble like New Orleans or Havana, nicknamed the “Conch Republic.” Before unofficial Key West mayor Jimmy Buffett put the rascally port on the map, Hemingway staked claim to its infamy there, along with the six-toed cats housed at his former getaway-turned-museum, one of Key West’s top attractions and conveniently located near the legendary Green Parrot saloon.
Any excursion through the Keys is a bucket-list road trip for the snorkeling, azure-tangerine sunsets, food and drink, and casting for all that bonefish, pompano, grouper, cobia, snapper, and tarpon. There are pockets of white sandy beaches à la the Mediterranean on the way. And some damn fine, five-star accommodations in the form of Isla Bella Beach Resort and Ocean’s Edge Resort & Marina.
Follow the winding road off the highway and into Isla Bella (“Beautiful Island”), which opened in mid-2019 bringing a fresh breeze to the Keys, and guests will find a streamlined Gulf-side sanctuary sprawling over 24 acres of tropical gardens, including rare sand dunes, five stunning oceanfront saltwater swimming pools, and a water-sports marina. Besides a pampering spa and full gym, you’ll also find four completely distinct restaurants within, including a cool new sand-in-the-toes sushi cabana that’s one of our area favorites.
The marina is the launching pad for fishing charters, jet ski tours, and harbor cruises, as well as kayaking, snorkeling, paddle-boarding and scuba-diving. Located in Marathon between Key Largo and Key West, the 199-room resort puts occupants at arm’s distance from party-hearty Duval Street to fully experience the tranquil Keys. The spa is exceptional, and known for its full-body exfoliation and hot stone massage. That one-two punch is called “Margarita on the Rocks.”
The three-story hotel, following a nautical blue-and-white motif, hits all the mile markers: Airy minimalist suites, killer oceanfront views from all rooms with terrace-to-sand first floor spaces, world-class spa and cuisine, and imaginative activities for everyone. There is a bocce ball court and giant chessboards. Want to run with the dolphins? The hotel provides a guide for jogging the pedestrian-lane Seven Mile Bridge. Guests can even join the staff in cleaning up the ocean’s morning beach debris, or ogle the resident manatee.
The choices for dining are so wide that guests have no reason to leave the property if they prefer. The showcase is Mahina, which features local fare riffing off Hawaiian Regional cuisine. Sushi Cabana is a brand new al fresco restaurant, offering the finest of local seafood, edging the Yellowfin swimming pool. Enjoy a cheeseburger in paradise at the Burger Palace, or some luscious tropical libations at the beachside bar. Mornings are for the Marketplace, a quaint coffee shop with fun sundry accessorizing. No wonder Travel + Leisure recently ranked Isla Bella one of the top resort hotels in all of Florida.
Heading south, adjacent to Key West on Stock Island, Oceans Edge Resort & Marina is a laidback spread, sprawled across 20 acres and known for its 165-slip marina where sportsmen can dock and bring in their fresh catches to the restaurant, the Yellowfin Bar & Kitchen. The light-filled dining room grills them to their choice. The happy hour, often with live bands, is a local favorite. Catch-of-the-day tacos and poke bowls are their signature dishes. All seafood is sourced from surrounding waters.
A rarity in any hotel, Oceans Edge’s Stock Market actually sells liquor along with various sundries for hitting the beach or bringing a reminder home. Besides six saltwater swimming pools, the hotel provides glass-bottom boat tours and fishing trips. Or take a kayak into the glades. Crisp local style is how the hotel describes their waterfront rooms and terraces. Like the Isla Bella, the color scheme is simplistic blues and whites, but with a touch more Floridian pop. Think relaxed comfort, furnished balconies and spa-like baths.
An angler’s paradise, the 175 suite hotel is favored by activity-seeking vacationers and locals who dock their boats there or stop by after fishing to a nibble and a sip, such as blackened shrimp tacos and a Salty Dog. Talk is less about current news events than what’s biting that day. The suites and the bar, in a pleasant way, are a kind of Tommy Bahama-meets-Tommy Hilfiger scheme. Nautical prep.
If guests want to step out nearby, Yahman’s Authentic Jamaican Jerk Shack is a best bet. The hotel provides free cruiser bicycles, paddle boards, and kayaks to explore the lagoon. Giant tarpon are often seen along the dock, trailing the tosses when fishermen are cleaning their catches. The configuration of the cottage-style hotel spread gives the vibe of a seaside residential enclave. And to that effect, Oceans Edge is actually reached at the end of a small neighborhood lane on Stock Island. Plus the hotel provides a 10-minute shuttle to Key West’s Duval Street on the hour, daily.
For the scenic cruise down from South Beach we eschewed a traditional rental car in favor something with a little more style from Turo. A sort of Airbnb for vehicles, Turo has a massive selection of rides you can book via their website or app, with everything from six-figure supercars to classics and compact convertibles on offer from trusted hosts. Miami is particularly fertile ground for scoring a cool ride on a budget, which is exactly what we did.
Such an epic stretch of road called for something sporty, so after browsing a bit from the comfort of home—with Turo you never have to deal with those tedious rental car counters—we selected a cherry red Maserati GranTurismo. It wasn’t brand new, but that’s not the point of Turo; the buy-in on this beauty was less than a mid-range Toyota at a traditional car rental spot. As always we read the reviews carefully to make sure we were getting a pristine set of wheels that would provide plenty of joy en route.
The GranTurismo boasts Pininfarina styling, a Ferrari engine, a heavenly exhaust note and the thrill only an Italian sports car can convey. The Turo rental process was seamless; for a nominal fee the host dropped the car off at our hotel so we were ready to roll down to the Keys bright and early and with minimal inconvenience. Heads turned as we flew down the the legendary Overseas Highway, a massive grin on our face. When planning your next road trip, this is an option you surely must consider; we’re sure glad we did.