Islamorada

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. 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're shopping for groceries, head to Marathon or Key Largo.