Islamorada is the smallest of the four “big” towns in the Florida Keys. Like Key Largo, the main attractions on Islamorada are fishing—it’s known as the “Sportfishing Capital of the World”—as well as snorkeling, diving, and relaxing. The town has its share of tourist-oriented kitsch along with its friendly small-town Florida vibe.

The weekend-long Islamorada Island Festival (Apr.) takes place at Founder’s Park (87000 Overseas Hwy.), with live music, arts and crafts, and the “Taste of Islamorada” contest in which local restaurants compete for various awards and the crowds get to sample their offerings.

The Islamorada Sport Fishing Festival (Sept.) was recently resurrected after a more than quarter-century hiatus. The event is aimed squarely at anglers, with product demonstrations, seminars, and a fishing tournament. There are also games, food vendors, and local artists displaying their wares.

Getting to Islamorada

Islamorada is located 83 miles (about 1.5 hours’ drive) south of Miami, about 23 miles (30 minutes) south of Key Largo, and about 77 miles (two hours) north of Key West. You enter the town from the north at about mile marker 91.