Celebrating Labor Day in the Florida Keys

Considering a Florida Keys Labor Day trip? Located just south of Miami, the place that comes to mind when you think of the Keys is likely Key West. However, there is much more to this stretch of coral islands than Key West, starting with the curious history of the Labor Day Hurricane of 1935.

This category 5 hurricane made landfall in Islamorada in the Upper Florida Keys. The tropical storm (which became known as the storm of the century) had devastating consequences, destroying the rail line that once connected Key West to Cuba.

However, the Labor Day storm led to a construction project of epic proportions: the Overseas Highway, which now connects the islands and is often referred to as the “Highway that Goes to Sea.” It features 113 miles and 42 bridges stretching across the Overseas Highway provide the backdrop for an amazing getaway.

Enjoy your weekend with one of these fun suggestions.

Try Craft Beers at Key West BrewFest

Photo Credit: keywestbrewfest via Instagram

The Key West BrewFest is a major tourist attraction for beer lovers, and there is no better place to try all the best award-winning brews.

The event, which runs from Wednesday to Labor Day Monday, was canceled in 2020 but is making a comeback this year - and it promises to excite! Spend the holiday weekend attending beer pairing dinners, beer brunches, and pool parties, as the Key West BrewFest features a packed schedule of events all over town. All proceeds benefit the Sunrise Rotary Club.

Plan Your Next Watersports Adventure

Photo Credit: keywestsunsetws via Instagram

If adventure is more your speed, the Florida Keys are an ideal place to plan your Labor Day watersports adventure. There’s no better way to experience the third-largest reef in the world than by getting out on the water.

Several tour operators offer all the water activities thrill-seekers crave, like parasailing, jet skis, and banana boat rides.

If more relaxing activities like snorkeling, kayaking, and glass-bottom boat tours are more your speed, there are plenty of those too. Companies like Fury Cat and Sunset Watersports Key West offer packages that cater to a variety of needs while allowing you to delight in the beautiful south Florida waters. Most catamaran tours also include complimentary breakfast and lunch.

Get Close to Aquatic Life at the Key West Aquarium

Photo Credit: keywestaquarium via Instagram

Looking for a kid-friendly activity on Labor Day? Head to Mallory Square to get up close and personal with sea creatures at the Key West Aquarium.

Even if you’re traveling without kids, the aquarium is an essential stop for marine life enthusiasts, as you can see and experience all kinds of sea animals. You can also explore one of its many interactive exhibits.

Visit the Ernest Hemingway Museum

Photo Credit: hemingwayhomemuseum via Instagram

Key West is where Ernest Hemingway called home, and his former residence has been converted into an extremely well-preserved museum. Visitors can take tours of his estate, which still has much of the original 17th century furniture.

It won’t take you long to understand why Hemingway spent ten years of his life on Key West when you see the home’s luxury and beautiful grounds. Perhaps the greatest curiosity of the house is the cats who still roam the area, which are direct descendants of Hemingway’s cats.

Please note that the museum only accepts cash for admission.

Experience the Florida Keys Overseas Heritage Trail

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The Florida Keys Overseas Heritage Trail features ninety miles of trails (most of them paved), connecting Key Largo to Key West. Whatever outdoor activity you enjoy - biking, walking, skating, or cycling - the trail offers jaw-dropping views you won’t soon forget.

You can also access a number of national parks from the trail, like Biscayne National Park, Crocodile Lakes National Park, and the Everglades.

Visit Marathon

Photo Credit: dolphinresearchcenter via Instagram

Finally, if you love fishing, head to Marathon. You can book a charter for all kinds of fishing, such as reef, deep-sea, and flats fishing.

But even if fishing isn’t your thing, Marathon is still worth checking out as it features several attractions like the Dolphin Research Center and the Turtle Hospital.

You can also explore the Seven-mile Bridge, which was originally part of Florida’s East Coast Railway. Now it connects the Middle Keys and the Lower Keys and is a beautiful place to jog and walk.

Final Thoughts

As you can see, the Florida Keys have plenty to offer in the way of Labor Day fun. Whether you like food, outdoor adventure, or history (or a healthy mix of all three!), you’re in for a fun weekend in southern Florida.