Continuing south on US-1, Key Largo blends into Islamorada (pronounced “EYE-la-mo-RA-da”), the self-proclaimed “Sportfishing Capital of the World,” where anglers from all over the world come to try their hand at catching the elusive, hard-fighting bonefish that dwell in the shallow saltwater “flats” and the deep-sea tarpon, marlin, and sailfish. Though now famous for its fishing and fun-in-the-sun, Islamorada (Purple Island) used to be synonymous with death and destruction: On September 2, 1935, a huge tidal wave, whipped up by 200-mile-per-hour hurricane winds, drowned over 400 people trying to escape on what turned out to be the last train ever to travel along the old Florida East Coast Railway. Most of the dead were World War I veterans, members of the “Bonus Army” who had marched on Washington DC, in 1934 and had been given jobs working to build the Overseas Highway. A stone pillar at the south end of Islamorada, along US-1 at mile marker 82, was erected by the WPA to remember the event.
At the center of Islamorada sits one of the older tourist traps in south Florida: the Theater of the Sea (MM 84.5, 305/664-2431, daily, $34 adults), a funky friendly place where you can watch performing sea animals or even swim with dolphins ($199).
Islamorada is also home to what may be the most pleasant and plushest lodging option in the Florida Keys: The Moorings Village (123 Beach Rd., 305/664-4708, $409 and up), on the ocean side of mile marker 81.5. The Moorings is an idyllic and much-loved retreat, with 18 self-sufficient wooden cottages on 18 acres, alongside a beautiful 1,100-foot white-sand beach.
The Moorings also have a nice restaurant and café, both at Morada Bay: Pierre’s (81600 Overseas Hwy., 305/664-3225) which serves urbane renditions of traditional key favorites; and The Beach Café & Bar, both on US-1 at mile marker 81.6. For a more down-to-earth taste of the keys, try the nearby Green Turtle Inn (305/664-2006, Tues.-Sun.), where specialties include shrimp-and-grits and local fish.