In the Florida Keys, the Conch Republic is less a nickname and more a state of mind. Despite lying only a couple of hours south of Miami, the islands feel like they belong to another universe. The archipelago offers a pristine paradise of white-sand beaches, aquamarine waters and coral-pink sunsets.
The Florida Keys carry a storied history as a magnet for outlaws, snowbirds and wanderers of all kinds — whether of the business or leisure variety. And my latest trip to the Keys included a mix of both, in fact.
Inspired by the success of a recent Gulf Coast road trip, my friend Aidan and I decided to head further south in the Sunshine State and organized a group getaway to the Florida Keys this past winter. We assembled a coterie of sun-seeking cohorts, some of whom sought to network professionally with local artists and entrepreneurs while visiting the islands.
The coral and limestone island chain extends about 220 miles from Virginia Key to Loggerhead Key, from the Atlantic Ocean to the Gulf of Mexico. My friends had arranged for a five-night visit, first staying in Islamorada and concluding the trip on Stock Island in Key West. The first half of our trip was more relaxing, dedicated to enjoying the gorgeous nature and serenity of the islands, and we spent the latter half amid the lively joie de vivre of Key West.
Key West, the busiest, most populated island in the archipelago, has sizzled as a cultural hot spot for more than a century, since Ernest Hemingway put the beach town on the literary map. Given we were a group of writers (and readers, at the very least), the Hemingway Home on Whitehead Street was one local attraction we all visited together. But even if you’re more a Fitzgerald fan than a Hemingway devotee, the six-toed cats and lush gardens are a sight to behold, regardless. The author spent 10 years living and working at his home here, penning To Have and Have Not; Islands in the Stream; and, most famously, The Old Man and the Sea.
We would have made the famously dissolute author proud during our earlier excursions to Florida Keys Brewing Co., opened in 2015 and incorporating the islands’ famous local flavors, like Key lime, in its hops. But I found my spirit of choice further up the road, at Islamorada Distilling, another locally owned institution concocting its own dark, barrel-aged and spiced rums on site.
The six of us rented a couple of cars to explore the islands, making it easy for members of our group to sneak in a little networking between activities. It was easy (and scenic) to cruise between the keys. (Key is the term for any islet near the mainland in the Caribbean and South Florida.) The flourishing artist communities in the islands and the plethora of local entrepreneurs ensured the trip was as professionally rewarding as it was personally enriching.
Though we may have parted ways for individual adventures during the day, we always made sure to convene in the late afternoon before the famous sunsets cast a glow across the shallow turquoise waters of the Gulf of Mexico. Fittingly, the sunset is feted as a daily party at Mallory Square in Key West. The nightly street carnival features street performers, live music, local artists and island psychics — the perfect blend of whimsy and festivity set against the breathtaking backdrop of the reddish-orange setting sun.
Of course, visiting the Florida Keys without sampling the famous Key lime pie is nearly blasphemous. When some of my friends set off to network or meet up with professional contacts on the island, the rest of us set out on what was, at first, an unofficial Key lime pie tasting tour of Key West and beyond. We tasted our favorite variation of the pie at the legendary Kermit’s, where we signed up for a pie-making class; and though the results were delicious on site, I must confess I’ve yet to successfully recreate that tart, tasty confection to such perfection back in New York. Perhaps it tastes better after a few rum runners (a signature Keys cocktail).
We enjoyed more delicious meals at Robbie’s Marina, where we fed tarpon from the dock, and Chef Michael’s, where a spectacular sunset over Florida Bay accompanied the freshly caught seafood. As for nightcaps, we visited Virgilio’s, an outdoor martini bar beloved by locals and tourists alike. Meanwhile, Sloppy Joe’s, a former Hemingway haunt, is a must-visit destination when sampling Key West nightlife.
At the end of our visit, Aidan and I felt immensely proud of organizing a group trip that proved a huge success for all our friends. The variety of adventure and activity on the islands — from fishing and boating to gallery-hopping and crafting — allowed everyone to pursue their own individual interests. We’d found our own perfect slice of paradise to accommodate all our needs and desires … and enough Key lime pie, conch fritters and rum runners to last us until next winter, at least
LODGING
Islander Resort
This idyllic retreat sits upon 24 acres of Islamorada’s most picturesque coastline; rise at dawn to watch the sunrise cast a pink glow across the turquoise waters.
81200 Overseas Highway, Islamorada, Florida
$$$
Little Palm Island Resort & Spa
Seaside serenity awaits at this 4-acre, adults-only private island where 30 thatched-roof bungalows boast outdoor showers, fire pits and hammocks overlooking the white- sand beaches of Little Torch Key.
28500 Overseas Highway, Little Torch Key, Florida
$$$$$
The Perry Hotel Key West
This 100-room boutique hotel proves an elegant waterfront oasis 4 miles east of downtown Key West. The Stock Island hideaway honors its maritime heritage with delectable boat-to-table cuisine.
7001 Shrimp Road, Key West, Florida
$$$
DINING
The Fish Camp
Taste the Old Keys “on the backside of paradise” at this beloved local hangout overlooking the mangroves. Expect tiki cocktails, freshly caught seafood, live music and a lively Sunday barbecue.
5 Geiger Road, Key West, Florida
$$–$$$
The Stoned Crab
Two private fishing boats deliver the islands’ most famous local seafood, stone crab, to this dockside institution. Other specialties include spiny lobster and Key West pink shrimp.
3101 N. Roosevelt Blvd., Key West, Florida
$$$–$$$$$
Sundowners
Enjoy beachside dining along Florida Bay with panoramic sunset views and delectable Key lime pie. Head to dinner early to feed tarpon off the dock at 4:30 p.m.
103900 Overseas Highway, Key Largo, Florida
$$$–$$$$
INFO TO GO
Though Key West International Airport sports only one runway, it offers daily direct flights to 22 domestic destinations via six airlines: American Airlines, Delta Air Lines, JetBlue, United Airlines, Silver Airways and Allegiant Air. Non- stop service is available to New York (LGA), Boston (BOS), Chicago (ORD or MDW), Dallas (DFW) and beyond, but international flights often connect through Atlanta (ATL) or Miami (MIA). The airport lies only 2 miles from Key West, and ride-share services such as Uber and Lyft are available on the island. Car rental kiosks are stationed at the arrivals area, with taxis queued curbside outside baggage claim. Florida Keys Marathon International Airport offers another option, servicing only private aircraft.
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