With the prospect of a three- to four-hour drive from Fort Lauderdale to Key West, flying directly to the southernmost point in the US offers a convenient, if costly, option for those travelers on tight schedules. But the balmy, flat, and winding 110 miles of the Overseas Highway that run from the Florida mainland to the bottom of US-1 will yield wild and weird corners for those able (or willing) to take the time.

From the geological wonders of Devil’s Milhopper to the picturesque sands of Bahia Honda, Florida has a varied and truly amazing state park system. One of its most distinctive parks is also one all too easily overlooked on a drive through the Keys. Located a half-mile, ocean-side, off Islamorada lies the lush but unassuming Indian Key Historic State Park. Accessible only by boat, the uninhabited 11-acre island was, two centuries ago, the original county seat for Dade County.

But that simple historical fact doesn’t begin to belie the tranquil key’s colorful and, at times, lurid history. From here, Jacob Housman built a formidable “wrecking” business in the early 19^th century, salvaging valuable cargoes from ships that met their ends on the treacherous reefs in the surrounding waters. In 1838, the Philadelphia botanist Dr. Henry Perrine moved to the island, bringing with him a host of non-indigenous flora, including agave (used in the manufacturing of sisal), tamarind, and large yucca plants. By the close of that decade, the island boasted a population of about 60, and even a nationally advertised resort hotel. Later, Henry Flagler would use the key as a base for dredging operations during the construction of his Overseas Railroad.

But Indian Key’s golden heyday drew its last breaths in the wee hours of August 7, 1840, when an invasion force of more than 130 Spanish-speaking Seminoles descended upon the island from nearby Lower Matecumbe Key. Twelve hours later, six people were dead (including Perrine) and much of the looted settlement laid in smoldering ruins. The United States Navy subsequently used Indian Key as a base of operations for the Second Seminole War, but the island’s halcyon days as a thriving, self-sustaining commercial center were effectively done.

Today, visitors may rent canoes and kayaks from Robbie’s of Islamorada and paddle out to Indian Key. Make the most of the trip by enlisting the services of historian, author, and tour guide Brad Bertelli of Historic Upper Keys Walking Tours to bring the island’s crumbling foundations and crunching gravel streets back to bustling life. If you appreciate vivid detail, humor, and a healthy overdose of enthusiasm for esoterica in your docent, then the affable Bertelli – who, with co-author David Sloan, recently published Bloodline: A Local’s Guide to 50 Famous Film Locations in the Florida Keys, an indispensable, trivia-packed self-guided tour for fans of the Netflix Original Series Bloodline – is your man.

Back in Islamorada, at the Florida Keys History & Discovery Center, where Bertelli also serves as the Curator/Historian, a fine scale model of Housman-era Indian Key provides additional perspective.

It is worth noting that there are no restroom facilities, nor fresh water, nor trash cans on Indian Key. But there is some decent snorkeling off its craggy northeastern shore. So any which way, plan accordingly.