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Rekindling Joy for the Timeless Florida Keys

“Repeat Visit To …” is an occasional series on VacayNetwork that explores leading global destinations by journalists who have had the opportunity to go beyond the iconic attractions and well-known highlights. In this instalment, contributing writer Jamie Ross returns to the Florida Keys to find it blissfully unchanged.

This is a journey that I have a vague memory of doing once before. It was March Break 1983, 40 years ago, when I jumped into a rickety old station wagon with three unsavory student buddies, and drove 35 hours from Canada to Florida on a Spring Break race for the sun. We purposely avoided the partying crowds in the popular mainland beach cities by continuing on as far south as the road would take us, the final stop on the Overseas Highway, and found ourselves in laid-back, free-spirited, artistic, quirky, and scenic Key West, a place closer to Cuba than to Miami.

For my return engagement, I approached the whole thing in a much more mature and civilized manner — not so much reveling in a continuous happy hour, more concentrating on the Keys’ history, important reef restoration, a turtle hospital, museums, and how an innovative and sustainable approach to crabbing has changed the industry.

The islands of the Florida Keys lie along the Florida Straits, dividing the Atlantic Ocean to the east from the Gulf of Mexico to the northwest. The highway is an engineering marvel, you’ll cross 42 bridges en route, some spanning stretches of water that seem impossible for a car to clear. The scenery is delightful, from the tidal flats and aqua-blue water dotted with tropical islands, to classic Americana roadside: kitschy shops, offbeat attractions, and funky restaurants. Drivers can travel the full (113-mile (181-kilometre) length of the Overseas Highway between the Florida mainland and Key West in four hours, but to fully experience the flavor of the Keys’ five regions, I suggest extending the road trip to four or five days.

Biking the Historic Seven Mile Bridge

My first stop was a historical wonder of the Keys — one of those astounding bridges. The Old Seven Mile Bridge, better known as “Old 7,” was built more than a century ago as the centerpiece of Henry Flagler’s Florida Keys Over-Sea Railroad. Now a bridge to nowhere, the Old Seven Mile Bridge began life as part of an overseas railway system built by the American tycoon with big money and even bigger dreams. Constructed from 1909 to 1912, the bridge was a key part of Flagler’s audacious and ambitious plan to create a rail line connecting mainland Florida to Key West.

When a new bridge was built in 1982, just prior to my first visit to the Keys, Old Seven fell into disrepair as a fishing pier. Recently, a five-year, $77-million refurbishment was completed on the 2.2 mile (3.5-kilometre) section from Marathon to Pigeon Key, and it opened in January 2022 for walking and cycling. So, I grab a bicycle from Bike Marathon Bike Rentals to pedal the newly opened section to historic Pigeon Key.

Florida Keys, Key Lime Pie, United States of America, USA, Marathon, Sunset, Southernmost Point Buoy, Marathon Turtle Hospital, Pigeon Key

Grab a bicycle from Bike Marathon Bike Rentals and pedal the newly opened section of the historic Old Seven Mile Bridge to historic Pigeon Key. At top: Kermit Carpenter sells smoothies from a small stand in front of Papa’s Restaurant in Key West. He began the business more than 29 years ago during his tenure as Papa’s bookkeeper. (Jamie Ross photos for VacayNetwork.com)

Pigeon Key is one of the Florida Keys’ most historically significant locations. In the early 1900s, the island housed more than 400 of Flagler’s workers. Today, the five-acre Key is a fascinating historic site, with a small museum dedicated to Flagler’s dream, while also telling the story of his poor workers who suffered in terrible conditions.

Fine Beer at Florida Keys Brewing

After biking home from Pigeon Key to Marathon, in a head wind, I earned a beer from Florida Keys Brewing Company. The brewery and taproom opened in March 2015 and infuses its brews with local flavors such as key limes, citrus, and local honey. Just as Flagler had done a century prior, Craig McBay took a chance and followed his dreams south. The Canadian left Ontario in 2000 and eventually landed in Islamorada where he and his wife, Cheryl, opened the area’s first microbrewery. [Discover More: Canadian Finds Winning Recipe at Florida Keys Brewing Company.]

Ask McBay how he comes up with the fanciful names for his different beers on tap, and he will regale you with stories of each of his 20 or so brews: Big Dick is in honor of a departed friend, Iguana Bait is infused with the pesky reptile’s beloved hibiscus, and Bale Beach Pale Ale is a nod to the Key’s disreputable past when packages of drugs or cash would wash up on a nearby beach.

Florida Keys, Key Lime Pie, United States of America, USA, Marathon, Sunset, Southernmost Point Buoy, Marathon Turtle Hospital, Pigeon Key

Tonight’s main event! Watching a Key West sunset has always been a nightly tradition that attracts thousands of tourists each year. (Jamie Ross photo for VacayNetwork.com)

Custodians of the Sea

Situated in the heart of the Lower Keys and only 24 miles (39 kilometres) from Key West, Mote’s International Center for Coral Reef Research and Restoration is a fully equipped marine science facility dedicated to marine research and education. Coral reefs are considered the rainforests of the oceans, supporting marine life, protecting shorelines and providing food and economical benefits to humans. Mote is working with NOAA’s Florida Keys National Marine Sanctuary and the Nature Conservancy to advance culture methods for hard coral restoration.

“Our Florida coral is functionally extinct and it is going to take some swift human intervention to bring it back to a sustainable system,” warns Allison Delashmit, regional director of operations at the facility. “The big picture is the loss of reef will have a ripple effect on everything. Fish and other big predators will leave. It will cause a whole ecosystem collapse. Since the 1960s we have lost close to 80 percent of our reefs here in the Keys.”

As tours of the facility help educate visitors on the plight of the fragile reefs, so to do educational tours of the Turtle Hospital in Marathon. The tours introduce visitors to the resident sea turtles and the hospital’s curative programs for loggerhead, green, hawksbill, and Kemp’s ridley turtles. The hospital is one of the few veterinary centers in the world dedicated solely to the care of sea turtles. Opened in 1986, the hospital treats injured sea turtles and, whenever possible, returns them to the wild.

Florida Keys, Key Lime Pie, United States of America, USA, Marathon, Sunset, Southernmost Point Buoy, Marathon Turtle Hospital, Pigeon Key

The Southernmost Point Buoy,  established as a tourist attraction in 1983 by the city at the corner of South Street and Whitehead Street, marks the southernmost point in the continental United States. (Jamie Ross photo for VacayNetwork.com)

For Whom Key West Tolls

I craned my head out the van window as we arrived in Key West, seeing familiar sites in the coolest, funkiest, most eclectic, and offbeat little city in America. There are tourists in floral shirts, baggy shorts and panama hats, locals dressed in whatever strikes their fancy, including a fellow in a Spider-man costume, all striding up and down the quaint, palm-shaded streets amongst the town’s 19th-century charm.

A large portion of Key West is a designated historic district with architecture dating to the 19th and early-20th centuries. Homes both grand and modest sport plantation shutters, wrought-iron railings and charming verandahs, a style imported from the Bahamas. One of these housed the Keys’ most famous resident, author Ernest Hemingway, from 1931 to 1939. A guided tour of the home, pool, writing studio and garden, complete with a stone urinal he claimed ownership of and took home from his favorite bar. His studio, where literary miracles were spun, is exactly as he left it, and about 50 descendants of Hemingway’s cats roam throughout the museum’s lush grounds.

I checked into my downtown hotel and then headed to Mallory Square just in time to watch an iridescent sun melt into the blue sea. While artisans flogged unique handicrafts on the docks of the historic square, jugglers, acrobats, fire-eaters, stilt walkers, and performing cats drew applause from sunset revelers celebrating a daily ritual that never seems to disappoint.

Florida Keys, Key Lime Pie, United States of America, USA, Marathon, Sunset, Southernmost Point Buoy, Marathon Turtle Hospital, Pigeon Key

The Marathon Turtle Hospital opened in 1986 as one of the few veterinary centers in the world dedicated solely to the care of sea turtles. (Jamie Ross photo for VacayNetwork.com)

The nightlife is also a spectacle not to be missed, a mixture of cultures, rhythms, and lifestyles. As it was during my visit those many years ago, Duval Street was the hub, a bit wild, but that’s part of the charm. I grabbed a stool at Sloppy Joes and raised a glass to Hemingway. Then I headed off to check if the toilet facilities had been replaced.

Island cuisine offers fresh seafood, including stone crab claws that boast a unique and sustainable twist on the crabbing industry. One claw is removed and the crustacean is then returned to the sea, where that appendage grows back. Other delicacies include shrimp, spiny lobster, and yellowtail snapper, done up with Caribbean flavors. A slice of key lime pie, the area’s signature dessert, is a heavenly end to any meal. There isn’t much debated about the world of politics here, but what is hotly contested is whether the region’s well-known and prized dessert should be topped with whipped cream or meringue. I found both delectable, even the strange chocolate-covered key lime pie on a stick.

Carol Shaughnessy, a transplanted Minnesotan who now works for the local tourism board, tells me that if you were born in the Keys, you are known as a “Conch.” A “Fresh-Water Conch,” like Carol herself, is someone who has lived here for seven years, and an “Honorary Conch” is someone who does something special for the region.

I suppose if it takes you 40 years to return to such a charming destination — well, you can call me a “Conch Fritter.” The Florida Keys have grown up some since my last visit, sure, but the friendly feel and laid-back simplicity of the place has not changed at all — the same charming details that rose above the fog of that long-ago visit remain: Key lime pie, ocean fishing, diving the reefs, buskers on the wharf, Sloppy Joes, sunsets, and old man Hemingway.


Where to Stay

The Islander Resort: The 24-acre, 115-room Islander Resort is located at mile marker 82.1 oceanside. Cottage-style units feature sleek, contemporary décor with screened lanais and upscale in-room amenities. Watersports, massage and wellness services, two pools, a hot tub, and a new family splashpad are among resort offerings. Dining options include Elements Lounge & Restaurant and the casual poolside Tides Beachside Bar & Grill.

Winslow’s Bungalows by Kimpton Key West: Nestled on the quiet end of old town, Winslow’s Bungalows features 85 guest rooms, three pools, a poolside bar, daily complimentary continental breakfast, and bike-share program. The boutique hotel, known for the many historic buildings across the grounds, is an easy walk to all of the nightlife, museums, activities, shopping, and dining Key West is known for.

Florida Keys, Key Lime Pie, United States of America, USA, Marathon, Sunset, Southernmost Point Buoy, Marathon Turtle Hospital, Pigeon Key

In the early 1900s, five-acre Pigeon Key housed more than 400 of Flagler’s Overseas Railway workers. Today, the five-acre Key is a fascinating historic site, with a small museum dedicated to Flagler’s dream, while also telling the story of his poor workers who suffered in some terrible conditions. (Jamie Ross photo for VacayNetwork.com)

Where to Dine in the Upper Keys

Marker 88: A Keys’ tradition since 1967, you will find beachside dining and amazing sunsets.

Backyard Café at Key Largo Fisheries: A waterfront cafe with a patio, featuring locally sourced seafood. Set in the back of Key Largo Fisheries, a source for seafood including lobster, stone crabs and shrimp, the eatery has been a favorite in the area since 1972.

The Keys Fisheries: The restaurant is the front house for one of the coast’s biggest fish exporters. Food is literally “fresh off the boat” and the restaurant is famed for its lobster Reuben.

Atlantic’s Edge at Cheeca Lodge & Spa: Atlantic’s Edge is a culinary journey through the Caribbean, infused with local, fresh ingredients native to the Florida Keys. The chef-driven restaurant is a modern take on island-inspired cuisine that celebrates cultural influences and the native cooking styles of islands from Islamorada to Cuba, Bahamas to Turks and Caicos.

Where to Dine in Key West

Conch Republic Seafood Company: Located in a former fish house building in the Key West Historic Seaport, the restaurant overlooks a working marina. The menu is based on local and Caribbean seafood with specialties such as conch chowder, blackened Florida Keys shrimp, and baked oysters callaloo.

First Flight Island Restaurant & Brewery: In the heart of downtown Key West, the brewery is well known for being the birthplace of Pan American World Airways and the place where Pan Am’s first tickets were sold in 1927.

Bistro 245 at Opal Key Resort: Enjoy casual dining with breathtaking views of the Key West Harbor. Fresh pasta, Black Angus beef, and Key West shrimp are just a few recommended choices.

Blue Heaven: Home to the most “heavenly” breakfast in Key West (try the seafood eggs Benedict and the homemade banana bread), the shuttered blue building has a century-old history in the historic Bahama Village neighborhood. Through the years, the venue has hosted cock fighting, gambling, and Friday-night boxing matches refereed by Ernest Hemingway.

More Information: www.fla-keys.com