By Michael Baginski/ The Florida Keys isn’t your typical Florida (or U.S.) destination. Sometimes quirky, always laid back, the Keys stretches for 200 km south from Miami over the Atlantic Ocean, Florida Bay, and Gulf of Mexico, boasting great year-round weather and a feeling of being in the Caribbean without leaving the North American continent.
“In the Florida Keys, we’ve always been a little bit different, a little bit off, we’ve always been a place apart,” says Chad Newman, Film commissioner and news director of the Florida Keys News Bureau. “And it comes from our culture, the history of the Florida Keys. We were started up by pirates and drug smugglers and people from different places, like Cuba and the Caribbean. So, there’s always been an amalgamation of cultures that have built up what Key West and the Florida Keys is today.”
And importantly for prospective Canadian visitors – who make up the Keys No. 1 international market (including snowbirds) – Newman says Keys residents generally maintain a world view where “We are very accepting; we embrace our differences. The official motto of the Florida Keys is ‘We are all one human family’ – and we live that every day.”
To that end and when some Canadians are casting a wary eye at travel south of the border, Newman emphasizes, “Don’t paint us all with one brush.”
“We actually seceded from the United States – in a joking manner – in the ‘80s,” he says of the short-lived Conch Republic, adding, “And ever since then, we’ve leaned into that. We’re just a little bit different, a little bit separate from the rest of the United States.”
Any plans to separate again now, we asked. “Nothing official,” he laughs.
In the meantime, the Keys will carry on in quirky style, with its inclusive attitude and fun and unusual events and festivals, like Hemingway Days and Fantasy Fest, an underwater museum, Key Lime pie eating contest, Mermaid festival, and much more.
There is also a huge Pride presence and corresponding festival.
Beyond the human element, the Keys is an idyllic archipelago of 1,700 islands and an eco-paradise of beaches, shallow-water flats, mangrove islets and coral reefs, providing habitat for a vast array of wildlife, including white herons, roseate spoonbills, pelicans, sea gulls, ospreys and countless underwater creatures including sea turtles.
There are also amazing ocean views for those driving the Overseas Highway (Highway 1), which ribbons its way from just south of Miami all the way down to Key West through The Florida Keys Marine Sanctuary – an area of natural beauty that “seems to be a world away from big cities and theme parks.”
Starting roughly 45 minutes south of Miami, the approximately four-hour drive traverses 42 bridges – including the iconic Seven Mile Bridge – comprising what Orbitz calls “one of the most spectacular road trips of your life… a dazzling buffet of tropical landscapes, cotton candy skies and water in every imaginable shade of blue and green.”
Those stopping along the way will find charming boutique hotels, restaurants serving fresh seafood, and array of activity opportunities ranging from fishing, sailing, diving and other watersports, to museums, historical and cultural offerings, flora, fauna, and boutique-type shopping experiences.
And at the end of the road, the marvellous pot of gold – charming, colourful, Key West, the southernmost continental point in the U.S.
With high season (January-April) just around the corner, Canadians will find five diverse regions that have “something for everyone” and a “small-town vibe where everybody is friendly and ready to welcome you.”
Here’s a breakdown:
Key Largo
First stop in the Keys on the drive south from Miami (about 100 km.), Key Largo is the longest island in the chain and is the gateway to John Pennekamp Coral Reef State Park, the first underwater preserve in the U.S. with 50 varieties of delicate corals and more than 600 species of fish. Visitors can scuba, snorkel or venture via glass-bottom boat excursion to the coral reef. Movie buffs can take a ride on the actual African Queen from the classic Bogart-Bacall film Key Largo, portions of which were filmed there.
Islamorada
The “new cool kid on the block” in the Keys, Islamorada has a great food scene, burgeoning arts district and is home to the Florida Keys Brewing Co. (owned by a Canadian). The destination is also heralded for its angling diversity and features the Keys’ largest fleet of offshore charter and shallow water “backcountry” boats, prompting claims that it is the Sport Fishing Capital of the World.
Marathon
Family-friendly Marathon is centrally located at the heart of the Keys between Key Largo and Key West and is home to both Seven Mile Bridge and Crane Point, a 25-hectare archaeological site that contains evidence of pre-Columbian and prehistoric Bahamian artifacts. Attractions include an intriguing museum, historic Adderley House, and several nature trails, one of which passes by the Marathon Wild Bird Center. Other attractions include a dolphin research centre and turtle hospital that welcome visitors, the Florida Keys Aquarium Encounters, and Pigeon Key, which pays homage to the construction of the first railroad through the Keys.
Big Pine and the Lower Keys
A place to nurture one’s connection to nature, the Lower Keys provide endless activity options, such as diving and back country kayaking, while Bahia Honda State Park is a prime example of the area’s natural beauty. Big Pine Key features a national refuge for miniature Key deer, tropical forest and even a few alligators. Popular nature tours offer opportunities to view migratory and wading birds and the unique flora and fauna of this tranquil natural area of the Keys.
Key West
A unique mix of Jimmy Buffet laid-back lifestyle and party central, Key West is the final stop on the Overseas Highway, where the land ends and meets the sea amid 19th-century charm and contemporary attractions. Continental America’s southernmost city, situated closer to Cuba than to Miami, is characterized by quaint palm-studded streets, century-old mansions and a relaxed citizenry of self-styled “conchs” (pronounced “konks”).
The city maintains connections to one-time resident Ernest Hemingway (including the annual Hemingway Days festival – July 22-26. 2026 – and its hilarious look-alike contest) and is a noted LGBT destination (Pride Week starts June 3-7, 2026).
But it’s during the upcoming Fantasy Fest (Oct. 17-26), that the town really gets the party going with a its “sizzling celebration that combines Carnival with Halloween.”
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