A darkly alluring Gothic labyrinth beckons at the center of this pastel town. Built in 1847, the cemetery crowns Solares Hill, the highest point on the island (with a vertigo-inducting elevation of 16ft). Some of the oldest families in the Keys rest in peace – and close proximity – here. With body space at a premium, mausoleums stand practically shoulder to shoulder. Island quirkiness penetrates the gloom: seashells and macramé adorn headstones with inscriptions like, ‘I told you I was sick.’
Get chaperoned by a guide from the Historic Florida Keys Foundation (305-292-6718), with guided tours ($15 per person) that usually go at 9:30am on Tuesdays and Thursdays. Call to reserve a spot.