Some of the islands you will travel on the Overseas Highway are Key Largo , Plantation Key , Windley Key , Upper Matecumbe Key , Teatable Key , Lower Matecumbe Key , Craig Key , Long Key , Conch Keys , Duck Key , Grassy Key , Crawl Key , Vaca Key , Bahia Honda Key , Spanish Harbor Key , Big Pine Key , Little Torch Key , Middle Torch Key , Big Torch Key , Ramrod Key , Summerland Key , Cudjoe Key , Sugarloaf Key , Saddlebunch Keys , Boca Chica Key , Stock Island , Key West .

Other Islands of note.
Upper Keys - Indian Key, Lignum Vitae Key, Shell Key, Rodriguez Key, Tavernier Key.
Middle Keys - Boot Key, Pigeon Key, No Name Key.
Lower Keys - Little Pine Key, Sand Key, Boca Grande Key.

While Looe Key no longer shows above water, having been eroded over the years, it is still an very active destination for diving so it is listed here with other real islands.

Almost 70 miles west of Key West lies a cluster of seven islands, composed of coral reefs and sand, called the Dry Tortugas. The main island is Garden Key where Fort Jefferson is, Loggerhead Key with a lighthouse, Bush Key, Long Key, Hospital Key, Middle Key and East Key.