For those who have spent time driving up and down the Keys, they have seen the green and white road signs announcing the names of the scores of islands stitched together by the asphalt and bridges used to build the Overseas Highway. Some of the islands are better known than others. Anyone with even a whiff of familiarity with the Keys recognizes names like Key West and Key Largo.
Islands connected by the highway like Knights Key, Big Pine, Bahia Honda, maybe even Ramrod Key, have less familiar names. That last one, Ramrod Key, found in the area of MM 26, was named after the ship Ramrod that wrecked on the reefs offshore in the early 1800s. Certainly, Marathon and Islamorada are familiar names, but no matter how many travel writers label them keys, Marathon Key and Islamorada Key are not real places. Marathon and Islamorada are both umbrella terms for collections of islands.
Considering the long, long list of islands making up the Florida Keys archipelago, and there are hundreds of them, some interesting name choices have been made. Concentrating on just those islands beginning with the letter “d,” some prime examples are the Desolation, Don Quixote, and Dildo keys.
The Desolation Keys are located northwest of Boca Chica Key. Boca Chica is the second to last island along the highway before reaching Key West — Boca Chica, Stock Island, Key West. The Desolation Keys are 2.5 miles north of the road. As is the case with nearly every island in the chain, Desolation was not their only name. On an 1861 U.S. Coast Survey, the islands were identified as the Dissolution Keys. The U.S. Coast & Geodetic Survey Chart no. 169, dated 1878, noted Desolation Keys. In 1909, U.S. Coast Survey Chart no. 585, “Key West Harbor & Approaches” also designated the islands as Desolation Keys.
They have also been called the Grassy Keys. The name Grassy Keys should not be confused with the more familiar Grassy Key. Grassy Key is one of the islands linked by the highway and probably best known because it is home to the Dolphin Research Center at MM 59. Locals know the island was home to Milton Santini, the man who caught and trained the television star Flipper (her real name was Mitzi). Mitzi, by the way, is buried on the grounds of the Dolphin Research Center.
Another curious choice of names is Don Quixote Key, located about one mile north of Horseshoe Beach. The beach is one of those places that locals have been chilling at for decades. It is found on West Summerland Key. In terms of the Overseas Highway, West Summerland is the island between Bahia Honda and Big Pine Key. In a 1935 report to The U.S. Coast & Geodetic Survey, “This small key lies to the south of No Name Key. The origin of the name is obscure, and the name is rather unusual. It is fairly well established locally.”
One of the more attention-grabbing names of all the Florida Keys is Dildo Key. Located seven miles south-southeast of Flamingo, the provocative name might not stem from the first thought that jumps to mind. An interesting thing about the word dildo is that it is a surprisingly old word that has been used to describe a phallic-looking object used for its imagined purpose all the way back to 1598.
In the case of Dildo Key, the name is based on something of a pricklier nature — Cerus pentagonus, a cactus sometimes called the triangle cactus, Night-Blooming Cerus, or the dildo cactus. The climbing cactus, readily found on the island, produces small, red fruits about two inches long that are a kind of dragon fruit. High in magnesium and fiber, dragon fruit is also known as pitahaya and strawberry pear.
Not to end this in the dumper, but the Dump Keys cannot be ignored for reasons Upper Keys backcountry fishing guides have understood for decades. The Dump Keys are between Plantation Key and Snake Bight and are, apparently, great places for fishing guides making the run to Flamingo and Cape Sable to make a comfort stop. Appropriately, the two islands were known as the Sh*t Keys for years. The name changed to the more reader-friendly Chit Keys, and is now marked on maps and charts as the Dump Keys.