Opening the Door to the Florida Keys: In Pursuit of the Perfect Pie

By Jane Muller |

A journey to find the best version of Key Lime Pie could happen nowhere but the Florida Keys, where the creamy, sweet, yet tart dessert has its origins.

Not into dessert? No worries. The search provided the subtext for a tour that explored more than a literal taste of the Keys. For appetizers, how about Burlington, Ontario’s contribution to local craft beer; the superpower of shipbuilders’ houses; the unseemly origins of Hemingway’s cat fountain; and where to find 300 varieties of rum under one roof?

Will Soto performs a juggling and high-wire act at the Sunset Celebration in Key West, Fla. Soto has been entertaining for over 30 years at the nightly celebration in Mallory Square that draws crowds of people to watch buskers perform, browse vendors’ wares and applaud as the sun sinks below the horizon beyond Key West Harbor. Photo by Rob’ONeal/Florida Keys News Bureau

The route is simple. There’s one way in and out of the Keys and that’s the Overseas Highway that traverses the 362-kilometre-long archipelago. The islands are linked by bridges, with Seven Mile Bridge providing the best sensation of skimming across the aquamarine-coloured water as if in a watercraft. If you’ve seen the movie True Lies, you’ll recognize where the action scenes were shot.

While the drive along the amazing bridge is a Keys visit highlight, cycling on the 2.2-mile remnant of the original bridge that runs parallel to the modern structure deepens the experience. We rented beach cruiser bikes from Marathon Bike Rentals, complete with baskets, lights, locks and helmets and rode a couple of kilometres on bike paths to reach Old Seven Mile Bridge. It was built more than a century ago as part of oil tycoon Henry Flagler’s Florida Keys Over-Sea Railroad.

The narrow bridge was converted to accommodate motor vehicles in 1938 and was retired in 1982 when the federal government built a new span. Today it accommodates cyclists and walkers and provides amazing views. We stopped more than once to see creatures like sea turtles and stingrays and to photograph the stunning scenery.

Our destination was Pigeon Key, a tiny, five-acre island that we spied from the trestle above. The National Historic Landmark includes buildings that were home to 400 workers, mostly from New York, who built Flagler’s railway. There are daily guided tours, but you can wander the grounds on your own and explore the museum to learn more about those early residents and their incredible mission.

Ernest Hemingway Home & Museum in Key West, Fla. Winner of both the Nobel and Pulitzer prizes, the legendary author lived in the Spanish colonial villa with his second wife Pauline and their two children from 1931 to December 1939. Hemingway wrote many of his best-known works in the second-story writing studio, and the grounds are still inhabited by descendants of his six-toed cat. Photo by Laurence Norah/Florida Keys News Bureau

Chris Rowell, operations director at Pigeon Key explained that above us was the last portion of the railway to be completed, effectively stranding the workers until the job was completed in 1911. There was a rush to finish the project before Flagler died. The ensuing construction “marathon” gave the city where the island is located its name.

Flagler saw the potential of Florida and invested in its development, leaving his mark in many ways including his namesake paint colour, Flagler yellow. Several of the island’s buildings feature the cheery yellow that Flagler believed would boost the morale of the workers. Conditions were less than cheerful for those workers who doused themselves with kerosene and diesel fuel to ward off the swarms of mosquitoes.

Today’s residents include students and summer campers who spend a few days on the island to learn about marine science. The number of visitors has increased dramatically since the redeveloped Old Seven Mile Bridge opened in January of this year, according to Rowell. Taking a ferry to the island was the main option previously and a new vintage-look trolley was to begin shuttling visitors in the summer of 2022.

While on the island, we were reminded that the Florida Keys is a fantastic destination for bird watchers. Two osprey pairs were nesting near the shore, a Great White Heron patrolled the beach while warblers and other small birds could be seen flitting around the gardens.

Although we were lucky enough to see a sea turtle while cycling to the island, a sighting is guaranteed at Marathon’s Turtle Hospital. Several permanent residents wouldn’t survive if released, though there are also cute little hatchlings awaiting release. In operation since 1986, the hospital has successfully treated more than 2,000 sea turtles. Tours run seven days a week. Reservations are recommended.

Florida Keys Brewing Company located in neighbouring Islamorada also offers tours. Craig McBay who co-owns the brewery with his Floridian wife Cheryl, shared the history and evolution of the first craft brewery in the Keys while walking us through the taproom, brewing operations and the beer garden where a tasting flight confirmed the reason for their success. The Burlington, Ontario native began home brewing and “started making good beer.” That started Cheryl thinking about requests for local beer that she’d been hearing for years working as a server in the Keys.

In March 2015 they gave the area its first craft beer. Craig is the head brewer and Cheryl, dubbed the creative powerhouse of the team, designed the mermaid tap pulls, beer cap mosaics seen throughout the property and the striking murals in the brewery. In her design of the brewery’s logo, she included a small conch shell and red maple leaf as a nod to each of their heritage.

Located halfway between Key Largo and Key West in the Morada Way Arts and Cultural District, the taproom and family-friendly tropical beer garden are open daily.

While craft beer is relatively new to the Keys, rum has a long history. A trickle of rum runs through the Key West Food Tours Hemingway-themed experience, as it should, given the famed author’s penchant for rum laced with grapefruit and lime juice. That was his version of the Papa Doble daiquiri, which left out the sugar and doubled the rum. 

A sweeter cocktail was served at the historic Rum Bar that features what could be the largest collection of commercial rum, with more than 300 varieties. A tasting experience includes flights of five, seven-ounce rum shots. Our refreshing cocktail was the perfect prelude to a visit to the Ernest Hemingway Home and Museum.

There are many great reasons to take part in a guided tour and all of them were revealed during this exploration of Key West. The destinations, food and libations speak for themselves, but a great tour requires engaging guides, and that’s what Maxwell Irwin and Dana Calyton delivered.

In a city with more than 300 restaurants in four square miles, some qualified guidance is appreciated. Irwin provided highlights of several of the island’s best eateries, great deals and unique offerings. We met up at the family-owned El Siboney Cuban restaurant that has been serving authentic dishes for more than 50 years. Traditional rice and beans, tender pork and house-made sangria fueled us for the walk that fed us a steady stream of stories like how the watery hue of “haint” blue paint on front porch ceilings wards off the evil spirits of lost souls that are unable to cross water.

A tour of Hemingway’s house was an opportunity to get through the front door of one of the most impressive residences on our trek. The house is open daily and offers walk-in tours followed by a chance to check out the grounds at your leisure. That’s where the cat fountain can be seen, an example of Hemingway’s drunken exploits and his wife Pauline’s creativity.

Hemingway and a friend dragged a trough-shaped urinal home from a bar and left it in the garden. To disguise the offending fixture, Pauline transformed it with decorative tiles and a suspended clay pot spouting a stream of water where their six-toed cat could get a drink. The cat’s descendants drink there today, wander the gardens and lounge around the house, oblivious to visitors.

Another water feature is the 24- by 60-foot swimming pool, a rarity in the 1930s. It was constructed while Hemingway was away covering the Spanish Civil War. The typewriter that accompanied him, complete with its wooden case, is among the items displayed in the expansive home with its opulent chandeliers in place of ceiling fans and art deco tiles imported from France for the bathroom floors. His Key West home facilitated his passion for fishing, something shared by visitors to and residents of the Florida Keys, home to some of the best sport fishing in the world.

Commercial fishers supply local restaurants with fresh catches from the sea. While waiting for our requisite serving of Key Lime Pie at Kaya Island Eats, Irwin explained that limes came to the island from the sea. Sailors kept a supply on board as a source of vitamin C as did the sponge fishers. They’d mix turtle eggs with sweetened milk and add some lime juice to create a treat while at sea. The concoction was brought home with them and evolved into a cool custard pie when refrigerators became available.

Kaya’s authentic version is served as an individual pie, well worth the calories. Our first course of The Legendary Rasta Pasta showcased how owner Scott Taylor fuses flavours from his native Hawaii and the Caribbean with the Macadamia nut jerk pesto drizzled over goat cheese, mango, pineapple and cilantro.

There is a place in Key West where everything Key Lime is fused together in one shop and that’s where our guided tour ends and a full key lime immersion begins. We’re greeted out front by Kermit’s Key West Key Lime Shoppe’s owner Kermit Carpenter attired in a lime green chef’s hat and jacket, pin-striped pants and lime loafers.

Like a seasoned performer, he poses for photos, pie in hand. When it’s my turn, he must sense I’m up for some fun and plants the pie firmly on my chest. There’s nothing squishy going on and it takes just a second to realize it’s a fake pie that has landed on many a startled tourist.

Carpenter falls into the category of character that Carol Shaughnessy, Key West writer and publicist refers to during a later interview when she says the island is “full of character and characters.” Character includes the largest predominately wooden-built historic district, which includes more than 3,000 structures.

Back in the 1970s before preservation of the houses was mandated, Carpenter used to visit his grandmother in Key West and through her, learned to make Key Lime pie. He moved there himself from West Virginia more than 30 years ago, opened a concession stand and sold “six or so pies a day.” Now Kermit’s makes 400 pies daily between its Elizabeth Street bakery location and warehouse.

The shop features soaps, olive oil, cookies, candies, salad dressing, sauces, dry mixes, and bottles of his signature key lime juice which has his simple pie recipe on the bottle.

If we were searching for the best Key Lime dessert, his frozen key lime pie on a stick dipped in dark chocolate would have squeezed past all the competition.

Virtually every dining experience was an opportunity to try a version of Key Lime pie including breakfast at Blue Heaven, the former location of Hemingway’s boxing ring. The banana bread and the garden setting are also noteworthy.

Even the sunset cruise aboard a Sebago Watersports catamaran provided a Key Lime Pie tartlet to top off a yummy tasting menu. While the sunset is the star, the guitar-playing, request-taking, laugh-making singer was also stellar.

We ordered an entire pie at Keys Fishery in Marathon and didn’t regret the abundance even after gorging on incredibly delicious lobster Reuben sandwiches. Associated with one of the coast’s biggest fish exporters, the dock-front restaurant benefits from the freshest catches.

Conch Republic Seafood Company overlooks a marina in Key West’s historic seaport and is also famous for its dock-to-table fare. Go for the grilled option for the catch of the day instead of blackened to fully enjoy the mild flavour of the fish.

Turns out the top pie was served at Marker 88 in Islamorada. Our selection could have been influenced by the fact that it was our first dinner in the Keys, or the beach-front table with bench swings for seating, the excellent live music, and the sunset view.

Bistro 25 at Opal Key Resort is another prime location for sunset views over Key West Harbor where the nightly Sunset Celebration at Mallory Square brings street performers, musicians and arts and craft vendors to the area.

After finding the best Key Lime pie on the islands, the next challenge was to replicate it at home. Along with the memories and images, the taste of the Keys lingers.

To find more reasons to go, visit