Live Your Hemingway Fantasies in the Florida Keys
Catch your dinner, drink rum, watch a sunset, and get your creative juices flowing
For over a hundred years, the Florida Keys have long been the inspiration for stories — on film, in books, and in song. In Key Largo, Bogie and Bacall met intrigue during a hurricane, Ernest Hemingway wrote A Farewell to Arms in a tiny apartment in Key West, and Jimmy Buffett made a career out of crooning about sunsets and pirates.
It’s easy to fall in love with the Keys, starting with the drive.
About 40 miles from the booming city of Miami, the Florida Turnpike abruptly ends, turning into the Overseas Highway - named for the fact that in many places you are literally driving across bridges that connect one Key from the next.
While Key West gets the lion’s share of attention with its cruise ship port, Hemingway House, pirate stories, and bar crawls — the hidden gem is the middle keys where you’ll find fishing boats, unclaimed stretches of shoreline, waterfront bars, and tranquil resorts that are less about DJs and more about sipping on a cocktail as the sun sets.
Hawks Cay Resort, located at Mile Marker 61 on the Overseas Highway is directly in the middle of Key Largo (the northernmost Key, at Mile Marker 100) and Key West (which lies at Mile Marker 0). The 60-acre resort offers spacious lanais, waterfront rooms, and even entire townhouses for rent. One of the last true resorts, Hawks Cay offers everything from massages to pickleball lessons to encounters with a retired military dolphin.
But the true reason to come to the keys is to be around — and on — the water.
There’s no better way to play out those Hemingway fantasies of The Old Man and the Sea than by chartering a boat at Hawks Cay marina, stocking it with some local beer from nearby Islamorada Brewery or Florida Keys Brewing Co., and catching dinner. The Florida Keys hold some of the best fishing in the world, with people traveling the world over to reap her treasures that include grouper, mahi, wahoo, hogfish, tuna, snapper, and Caribbean lobster (when in season). A good fishing charter will show you the prime fishing spots and will clean and filet your catch.
Once off the boat, head over to Angler and Ale, located right at the Hawks Cay Marina. Grab a cold one at the bar, and hand your catch over to the chefs, who will cook it for dinner.
The restaurant offers a cook-and-catch program, where for only $25 a pound, the chefs will prepare your fish to your liking (blackened, fried, grilled, or sashimi) and present it with two sides of your choice (fries, seasonal vegetables, slaw, salad, or fragrant and tropical coconut rice).
Hawks Cay executive chef, Patrick Cleary, says that, although the Florida Keys are known worldwide as a mecca for fishing, not many restaurant offer cook and catch programs. “A lot of restaurants won’t let you just walk in with your fish,” he says. With Angler and Ale having a more robust program catering to fishing, Cleary can get about 40 people a day who bring in their fresh catch. “The local captains know about us and tell their clients. They’ll prepare and filet the fish so we can take it cooking ready.”
Cleary says the cook and catch program is a unique experience for visitors to the Keys — and a service to families who may want to go fishing but don’t want to waste their catch or cook while on vacation. “We cater to a family-style experience. Eating fresh seafood that you caught that day brings excitement to dining.”
If you prefer to sit by the pool or snorkel rather than catch your dinner, Cleary sources his fish daily from local fishermen. “I’ve known my local fishmonger for ten years and he supplies us with Key West pink shrimp, lobster, crab, grouper, snapper, and more.” On a recent evening, Cleary was offering hogfish, just brought in from local spearfishers. On a busy evening, the restaurant can go through 100 pounds of fish.
Cleary says the vast variety of local fish, combined with produce from nearby Homestead, keeps his imagination running. “I am a chef’s chef. I work in the kitchen and I want to cook food. We’re not buying frozen stuff. For me, I’d rather put something better out there than make a dollar.”
Before sitting down to dinner (or for a nightcap), a trip to the Hawks Cay Pilar Bar is a must. The outdoor watering hole is named after Hemingway’s beloved boat, the Pilar. Filled with Hemingway photos and memorabilia, the bar, itself, resembles the Pilar complete with captain’s chairs as bar stools. Pilar Bar offers rum tastings featuring Papa’s Pilar rum, made in Key West and inspired by Hemingway’s love of adventure (and the golden liquid), along with a selection of fine cigars and light fare.
The bar also offers a well-made Hemingway daiquiri, along with other cocktails perfect for a sundowner. Pilar Bar is located on the water, so you can watch the boats go by while fashioning your own story of your day on the water — just like Hemingway did decades ago.