Islamorada (Spanish for “purple isle”), the only settlement on Upper Matecumbe Key, marks the beginning of the Middle Keys. The island’s Hurricane Memorial (Mile 82) honors victims of the Labor Day hurricane in 1935, which washed out much of the railroad and was one of the most powerful ever recorded in the U.S.Two sites can be visited off Lower Matecumbe Key. Lignumvitae Key State Botanical Site (Accessible via boat tours from Robbie’s Marina. +1 305 664 9814. 7 days a week. Fare), an uninhabited 280-acre [113.3-hectare] island, contains a rare virgin tropical hardwood forest that includes gumbo-limbo, pigeon plum, and poisonwood. At the Indian Key State Historic Site (Also accessible via boat tours from Robbie’s Marina. +1 305 664 4815. Thurs.-Mon.; Fare), the foundations of buildings and cisterns from an 1830s wrecking village, established to salvage ships that had run aground on the reef, are still visible amid the tropical undergrowth.
At the Long Key State Recreation Area (Mile 67.5. +1 305 664 4815. Adm. fee), swimming is poor, but beachcombers may find the rubbery egg cases left by sea turtles. The Golden Orb Trail here leads through a delightful mangrove-edged lagoon.
The Long Key Viaduct sweeps toward tiny Conch Key, then Rte. 1 angles across Grassy Key and into Marathon, the heavily developed commercial center of the Middle Keys. Amid the sprawl is Crane Point Hammock, where you’ll find a thatch-palm hammock with the combined Museum of Natural History of the Florida Keys and Florida Keys Children’s Museum (Mile 50. +1 305 743 9100. $7.50 adults, $4 students, children under 6 free).