The “Sportfishing Capital of the World”: A Florida Keys Village with Beaches and Boutique Resorts

Driving along the Overseas Highway through the Florida Keys, you quickly realize that each community along the way has its thing. First, Key Largo — the “Diving Capital of the World.” Then, not to be outdone, there is Islamorada, the “Sportfish Capital of the World.” It’s a spot where anglers flock from all over the globe to try their hand far offshore for marlin, sailfish, and mahi-mahi, as well as to the backcountry for flats fishing, targeting tarpon, bonefish, and snook. It seems that in this town, there are as many different kinds of fishing and things to catch as there are islands in the Keys. 

But it’s a unique place for several reasons. The town’s official name is Islamorada, Village of Islands, because the incorporated area includes several neighboring keys. But to locals, Islamorada (or Isla, as they say there) refers to the cozy village located on Upper Matecumbe Key, between Mile Markers 79 and 83 — one of the best islands in Florida. It’s a close-knit small town, but also a spot full of beautiful resorts that range from exclusive enclaves to larger beachfront hotels. 

Thanks to its beautiful beachside resorts, extensive dining options, and laid-back island small-town vibe, Isla is preferred by many experienced Keys travelers to the busier islands like Key West or Marathon. It has a hint of the Old Florida that so many come here to seek, and if you’re seeking time on or beside the water, whether it’s casting a line, paddling a kayak, or lounging in the sand at a beach resort, it’s hard to beat Islamorada. 

A word of caution about the beaches in this part of the world: There aren’t many, and the best ones are at resorts. So, if you want to capitalize on beach time, you’ll need to book the right hotel. There are several choices located on the oceanside of the island, including Chesapeake Beach, Islander Resort, Cheeca Lodge, The Moorings Village, and Amara Cay Florida Keys Resort. Many more have small, beachy patches, which are good for swimming and launching kayaks.

But that doesn’t mean there aren’t a few spots worth checking out, regardless of where you’re staying. On the south end of Lower Matecumbe (Mile Marker 73.5) is Anne’s Beach. There’s a boardwalk and some pretty sand patches, best enjoyed at low tide. It’s a Keys beach, so don’t expect too much, but it’s possible to find a nice private place to hang out by the water, and the scenery is gorgeous. Another glorious way to spend the day is by kayaking or paddleboarding — the island’s mangrove-lined bayside has shallows full of wildlife. Plus, some of the nicest reefs for snorkeling are a boat ride away from the oceanside.

For a small island, there’s no shortage of options when it’s time for dinner. A trip to the Keys isn’t complete without a meal on the water, and Islamorada delivers. The Islamorada Fish Company is a road trip staple, with dockside dining under a tiki and enormous tarpon in the water (they’re fed regularly). Next door are two more top-rated choices: Morada Bay for sand-between-your-toes dining and Pierre’s for an upscale beachfront French experience, with 4.3 and 4.2 stars, respectively, on Tripadvisor. All three are located on the bayside and have amazing sunset views.