The Ultimate Guide to the Florida Keys

It’s easy to think of the Florida Keys as just that – ‘the Keys,’ a singular, undifferentiated destination. However, there are more than 100 islands in the Keys, each offering its unique angle of exploration. Therefore, let’s split the Keys into five distinct regions, each with its own theme, all connected by the Overseas Highway.

With that said, don’t think you can only go fishing in Islamorada or have family fun in Marathon. Each Key is its own island, but there is a wide array of attractions across the region that can be enjoyed, more or less, wherever you are. At the very least, you’re never that far from the next little stand of mangroves or South Florida eccentricities.

Key Largo: Dive In

Located about a 90-minute drive from Miami, the northernmost Keys are known as the Upper Keys. Like many of the islands’ towns, Key Largo, which sprawls along the Overseas Highway, feels like a blend between a fishing village and a dedicated coastal resort. This area is also the central hub for tourism in this part of the Keys.

This prominence is largely due to the presence of John Pennekamp Coral Reef State Park, which celebrated its 60th anniversary in 2023. Here, visitors will have the chance to see intricate forms of soft coral, vibrant schools of fish, formidable barracuda, and perhaps even massive, yet graceful, sea turtles. However, the coral in the Florida Keys is currently facing challenges due to disease, careless boating practices, and the adverse effects of climate change, such as rising water temperatures.

There are significant efforts underway to reverse this damage, and you can help by practicing responsible diving at any of the dive sites available in Key Largo. To access these, you’ll need to organize excursions through Pennekamp Park or at any of Key Largo’s many dive centers.

Molasses Reef is the most visited coral reef in the state, home to a rainbow of sea life, including some imposing but harmless Goliath Groupers. Because of its popularity, it’s easy to plan a trip out to Molasses Reef; however, due to the high traffic it can be quite crowded. Casual divers might not mind, but those seeking a more advanced and less congested diving experience may want to opt for the Duane and the Bibb, two US Coast Guard Cutters that were intentionally scuttled about a mile south of Molasses Reef. This location is ideal for advanced divers looking to explore marine life and enjoy excellent visibility.

For an even bigger challenge (and a rewarding experience), consider an excursion to the USS Spiegel Grove. This 510-foot wreck (also intentionally sunk) is said to be a unique dive that cannot be fully explored in one trip alone. This site is reserved for advanced divers, and even those with wreck diving certification should proceed with caution. Still, if you make it out here, you’ll discover an environment reminiscent of an underwater Manhattan during rush hour; the marine life here is truly extraordinary.

Islamorada: Get Hooked

The ‘Village of Islands’ is aptly named – a collection of several islands scattered across the deep teal waters of Florida Bay. This is where the Keys truly feel like islands, rather than an extension of the Florida Peninsula. Islamorada also proudly identifies itself as the sportfishing capital of the world, a claim that certainly holds water.

There’s a plethora of fishing charters available in Islamorada. An experienced captain, along with a good boat and some skill (and luck), are the best prerequisites for reeling in an unforgettable fishing story. Iconic species like sailfish, blue marlin, and swordfish are caught via charters throughout the year; winter boasts the best sailfish fishing, while the warmer months are when the latter two species are most active.

If you’re looking to be closer to the water without the noise of a motor, consider kayak fishing in Florida Bay. This unique approach allows you to stealthily pursue snook and permit fish, which are among the most elusive species in the area. It’s crucial to be fit for this type of fishing; if you think paddling is tiring, imagine doing so after battling a bonefish!

Marathon: Family Fun

Continuing south in the Keys will lead you to Marathon, essentially the midpoint across the islands. Marathon and the Middle Keys are especially family-friendly, featuring numerous nature-based activities. Curry Hammock State Park offers a straightforward 1.5-mile walking path through tropical hardwoods and mangrove habitats, as strenuous a ‘hike’ as you will find here. Alternatively, you can visit Crane Point, a combination museum covering the old Keys and nature preserve, showcasing several acres of rare palm hammock trees. If traditional beach experiences are what you seek, head to Sombrero Beach, where the fine sand and swaying trees resemble something out of a postcard.

Animal lovers will want to take time to stop at the Turtle Hospital, a rehabilitation center dedicated to treating and releasing injured sea turtles. Visitors can enjoy guided tours of the facility, typically lasting 70-90 minutes, concluding with an opportunity to feed some of the residents.

If you’re feeling hungry, start your day with breakfast at The Stuffed Pig; it’s delectable, but be warned—you’ll leave feeling quite full! Locals also rave about La Niña, a spot serving Cuban favorites like roasted pork with rice and beans, plus fried plantains—you certainly won’t depart hungry.

Big Pine & the Lower Keys: Camp the Keys

Big Pine Key may not be the most expansive of the Florida Keys, but it often feels like the most rustic island in the archipelago. This makes it a great destination for pitching a tent or parking an RV. If you’re interested in camping, Big Pine Resort offers approximately 10 acres of island ground for travelers eager to escape the hustle and bustle. However, our favorite camping experience is at Bahia Honda State Park, which boasts one of the largest and most beautiful beaches in the Keys. Here you can choose between tent camping or cabin rentals, though if you prefer the latter option, it’s advisable to act quickly as they tend to fill up swiftly.

Moreover, if you continue along the Overseas Highway, you can also find camping options at the KOA site on Sugarloaf Key, just a brief drive from Key West. While it may not be as rustic as Big Pine, it still provides a pleasant outdoor experience and serves as a budget-friendly home base for exploring Key West.

If you’re searching for classic diner-style food before departing Big Pine, be sure to visit the Florida Keys Cafe, where the hearty meals are as delicious as they are substantial.

Just east of Key West lies Stock Island, known for its shrimp boats that harvest the ‘pink gold’ of local waters. Many locals frequent this area for dining out—while some tourists may stop by, you’ll blend in with residents at eateries like The Docks, where the seafood was likely caught just hours ago. Alternatively, enjoy wood-fired pizza at Roostica or savor Cuban and Caribbean cuisine at El Mocho, which is well-rated for its value, or El Siboney, which is favored among locals.

Key West: Creative Culture

The Overseas Highway culminates in Key West, though the adventure through the islands is far from over. Key West is famously recognized as the most notable island in the chain, yet it feels distinctly unique. Historically, residents have engaged in fishing and salvaging wrecked ships, but for over a century, Key West has formed its identity as a hub for artists, the LGBTQIA+ community, and individuals seeking acceptance.

A fantastic starting point to discover Key West’s vibrant character is at The Studios of Key West, a nonprofit arts center displaying artist studios spread across three floors (a branch of South Florida’s famed bookstore is also located here). Visitors are welcome to explore the island’s artistic community or enjoy regular performances and readings.

Additionally, Fort East Martello Museum, originally intended as a fort, has transitioned into a museum showcasing the island’s eclectic arts and history. When the sun sets, don’t miss Mallory Square at the end of Duval Street, where a lively assortment of buskers and artists showcase their talents to the crowd, creating a truly captivating atmosphere. Finally, cap off your visit with a meal at Cafe Sole, offering a delightful fusion of flavors from South Florida, the Caribbean, and the south of France.