Early settlers named this key after their schooner, Island Home, but to make it sound more romantic they translated it into Spanish: Isla Morada. The Chamber of Commerce prefers to use its literal translation, "Purple Island," which refers either to a purple-shelled snail that once inhabited these shores or to the brilliantly colored orchids and bougainvilleas.
Early maps show Islamorada as encompassing only Upper Matecumbe Key. But the incorporated "Village of Islands" is made up of a string of islands that the Overseas Highway crosses, including Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, Craig Key, and Fiesta Key. In addition, two state-park islands accessible only by boat—Indian Key and Lignumvitae Key—belong to the group.
Islamorada (locals pronounce it "eye-la-mor-ah-da") is one of the world's top fishing destinations. For nearly 100 years, seasoned anglers have fished these clear, warm waters teeming with trophy-worthy fish. There are numerous options for those in search of the big ones, including chartering a boat with its own crew or heading out on a vessel rented from one of the plethora of marinas along this 20-mile stretch of the Overseas Highway. More than 150 backcountry guides and 400 offshore captains are at your service.
Islamorada is one of the more affluent resort areas of the Keys. Sophisticated resorts and restaurants meet the needs of those in search of luxury, but there's also plenty for those looking for something more casual and affordable. Art galleries and boutiques make Islamorada's shopping scene the best in the Upper Keys, but if you need groceries, head to Marathon or Key Largo.