Every island is distinct: Five unique adventures in the Florida Keys

It's easy to see the Florida Keys as simply 'the Keys,' a single destination. However, with over 100 islands, each one presents its own exploration opportunities. Let's break down the Keys into five unique regions, each with its own theme, all linked by the Overseas Highway.

That said, don't assume fishing is limited to Islamorada or family fun is exclusive to Marathon. Each Key is its own island, but there's a wide array of attractions spread throughout the region that can be enjoyed from anywhere. You’re always close to the next cluster of mangroves or the quirky charm of South Florida.

Key Largo: Dive In

Located about 90 minutes from Miami, the northernmost islands are known as the Upper Keys. Key Largo, which stretches along the Overseas Highway, resembles a blend of a fishing village and a coastal resort. It serves as the main hub for tourism in this area.

This is primarily thanks to John Pennekamp Coral Reef State Park, celebrating its 60th anniversary in 2023. Here, you can encounter intricately shaped soft corals, vibrant schools of fish, intimidating barracuda, and perhaps even graceful sea turtles. However, the coral reefs face threats from disease, careless boating, and rising water temperatures linked to climate change.

There are initiatives underway to combat this damage, and you can contribute by being a responsible diver at any of the dive spots listed. To reach these sites, you’ll need to book excursions through Pennekamp Park or one of Key Largo’s many dive shops.

Molasses Reef is the most frequented coral reef in the state, showcasing a colorful array of sea creatures, including the majestic yet harmless Goliath Groupers. While it's easy to book a trip there due to its popularity, it can get crowded. Casual divers may enjoy it, but those seeking a less busy experience might prefer the Duane and Bibb, two US Coast Guard Cutters intentionally sunk about a mile south of Molasses Reef, which offer an advanced diving experience with abundant marine life and excellent visibility.

For a greater challenge (and reward), consider an excursion to the USS Spiegel Grove. Many recommend multiple dives here, as this 510-foot wreck (intentionally sunk) cannot be fully explored in one visit. This site is for advanced divers only, and even certified wreck divers should not attempt to cover the entire wreck in one go. However, if you venture here, you'll encounter a scene that feels like an underwater Manhattan during rush hour, with marine life thriving at another level.

Islamorada: Get Hooked

Known as the 'Village of Islands,' this aptly named area consists of several islands scattered across the deep teal waters of Florida Bay. Here, the Keys truly embody the essence of islands, rather than merely extending from the Florida peninsula. Additionally, Islamorada proudly claims the title of the sportfishing capital of the world, a claim well-deserved.

Islamorada boasts an abundance of fishing charters, and the ideal combination of an experienced captain, a solid boat, some skill, and a bit of luck will set you up for a fishing tale to share with the grandkids. Iconic species like sailfish, blue marlin, and swordfish are available through charters year-round; winter is the prime time for sailfish, while the warmer months are best for the latter two.

For a more intimate connection with the water without a motor, try kayak fishing in Florida Bay. This approach allows for stealthy pursuits of snook and permit fish, known as the elusive ghosts of the Flats (shallow fishing areas). Be prepared for a workout, as paddling can be tiring, especially after battling a bonefish.

Marathon: Family Fun

Continuing south through the Keys, you'll reach Marathon, which serves as the midpoint among the islands. The Middle Keys, particularly Marathon, offer plenty of family-friendly nature activities. Curry Hammock State Park features a gentle 1.5-mile walking trail winding through tropical hardwoods and mangrove ecosystems, making it the most strenuous hike you'll find here. Alternatively, visit Crane Point, a unique blend of a museum showcasing the history of the old Keys and a nature preserve filled with rare palm hammock trees. If you're looking for a more classic beach experience, Sombrero Beach boasts soft white sands and swaying palms that seem straight out of a postcard.

Animal lovers and older kids will definitely want to check out the Turtle Hospital, a center dedicated to rehabilitating and educating visitors about injured sea turtles. Guided tours lasting 70-90 minutes allow guests to learn about the facility, concluding with an opportunity to feed some of the patients.

Feeling hungry? Start your day with breakfast at The Stuffed Pig; it’s delicious, but be prepared to leave feeling quite full. Locals also rave about La Niña, where you can indulge in Cuban favorites like roasted pork with rice and beans and fried plantains – again, you won't be leaving here hungry.

Big Pine & the Lower Keys: Camp the Keys

While Big Pine Key isn’t the largest island in the Florida Keys, it often feels like the most rustic of the group.

This makes it an ideal location for setting up camp (or parking your RV). If you're looking for such an experience, Big Pine Resort offers around 10 acres of peaceful island terrain for those wanting to escape the hustle and bustle. However, our top pick for camping in the islands is Bahia Honda State Park, which features one of the largest and most stunning beaches in the Keys. You can choose between tent camping or cabins, but if cabins are your preference, be sure to book quickly, as they fill up fast.

Further along the Overseas Highway, you can camp at the KOA site on Sugarloaf Key, just a short drive from Key West. While this island may not offer the same rustic charm as Big Pine, it still provides a pleasant outdoor experience and is an affordable base for exploring Key West.

If you're in need of hearty diner fare before leaving Big Pine, be sure to stop by the Florida Keys Cafe, where the food is as satisfying as it is tasty.

East of Key West lies Stock Island, famous for its shrimp boats harvesting the 'pink gold' of the local waters. This is a popular spot for Keys locals to enjoy a meal – while tourists are around, you'll find yourself mingling with residents at places like The Docks, where the seafood is likely to have been caught just hours earlier, or Roostica, a wood-fired pizza place that perfectly satisfies cravings for a great pie. For delicious Cuban and Caribbean cuisine, try El Mocho for good value or El Siboney, a favorite among locals. And gentlemen, if you’re in need of a haircut and a beer, consider visiting the aptly named Beards & Brews for both.

Key West: Creative Culture

The Overseas Highway culminates in Key West, yet the island's offerings are far from over. While Key West is undeniably part of the Keys – in fact, it’s the most renowned island in the chain – it possesses a distinct atmosphere. Though fishing and salvaging sunken ships have been historical activities here, for over a century, Key West has built its identity as a refuge for artists, the LGBTQIA+ community, and others seeking a welcoming space.

A wonderful starting point to explore Key West’s vibrant character is The Studios of Key West, a nonprofit arts center featuring artist studios spread across three floors (and home to a branch of South Florida’s beloved bookstore, Books & Books). Stop by to discover more about the island’s artistic scene or to catch regular performances, readings, and events.

The Fort East Martello Museum was originally intended to serve as a fort, but its purpose as a military site quickly faded. Instead, it has transformed into a museum filled with quirky artifacts, celebrating the art and history of the island. As the sun sets, make your way to Mallory Square at the end of Duval Street to witness a lively scene of buskers and local artists showcasing their talents (or, if you prefer, watch a dog perform on a tightrope). Wrap up your day with a delightful meal at Cafe Sole, which artfully combines flavors from southern France, South Florida, and the Caribbean.