The largest and longest of all the Florida Keys, hence the name, Key Largo was made internationally famous in the 1948 Bogie-Bacall film of the same name. Even before that movie (which, incidentally, was filmed almost entirely on a Hollywood soundstage), the island had an excellent reputation among sportfishing enthusiasts and intrepid vacationers.

Today, Key Largo still welcomes thousands of anglers as well as snorkelers and scuba divers who are eager to explore the underwater beauty of John Pennekamp Coral Reef State Park. The town itself is small-town Florida through and through, despite quite a bit of it given over to ticky-tacky tourist paraphernalia.

Over the course of May’s weekends, the loosely-themed Key Largo Food & Music Fest brings together concerts and food-sampling events across the island. The similarly spread-out Key Largo Food & Wine Fest (Aug.) sees a range of local restaurants offering special menus and pricing, along with wine-tasting events, progressive wine dinners, cooking demonstrations, art shows, and more.

Somewhat more cohesive (at least by Keys standards) is the Key Largo Pirates Festival (Oct.). Beginning with a “pirate raid” and parade, as so many of these buccaneer-themed festivals do, the festival features costume contests, an arts-and-crafts area, a parade, and, uh, underwater poker.

Getting to Key Largo

Key Largo is at mile marker 100 on the Overseas Highway, about 60 miles (1.5 hours drive) south of downtown Miami and about 100 miles (two hours) north of Key West.