Check out this great New York Times article describing a classic coastal road trip down the Florida Keys.  Link to the article is provided,  and an excerpt is below.  

44 Islands and 42 Bridges: A Florida Keys Road Trip by Elaine Glusac

A new self-guided tour available via a free cellphone app from the history museum Florida Keys History & Discovery Centerintroduces hurricanes, pirates and island pioneers, winding up back at Cheeca Lodge where many of these original “Conchs” were buried.

A model of Indian Key at the Florida Keys History and Discovery Center in Islamorada, Fla. Credit Scott McIntyre for The New York Times

To delve deepest into Keys history, Brad Bertelli, the curator of the Florida Keys History & Discovery Center told me, travelers have to leave the road at Islamorada, and become waterborne.

He and I launched rental kayaks from Robbie’s marina in Islamorada, a popular stop for feeding tarpon the size of teenagers, and headed for the offshore Indian Key Historic State Park. The 11-acre, mangrove-fringed island, with a shady tamarind grove and spiky sisal plants bordering the paths, holds the remains of a 19th-century wrecking village devoted to salvaging goods from ships that ran aground on the reef.

In the 1830s, Indian Key was the seat of Dade County, site of a bowling alley and an inn promising “one of the most favorable situations in the United States for persons who are suffering from pulmonary, dyspeptic and numerous chronic diseases, and obliged to seek refuge from the chill blasts of a northern winter,” according to a sign posted on the site. Prominent Keys travelers, including the ornithologist John James Audubon, passed through.

“Wreckers were thought of as the pirates of the day,” said Mr. Bertelli, looking the part with a bandana tied around his head. “Like used car salesmen, there were some bad apples.”

Today, the ghost of its town square is a large field surrounded by rock foundations of storehouses, cisterns and homes, eventually abandoned after the Second Seminole War in 1842. A three-story observation tower offers views to distant Alligator Lighthouse, marking the reef where the wreckers plied their trade, and, in the opposite direction, Lower Matacumbe Key, the source of fresh water, which allowed the island to flourish.