The EvergladesChokoloskee is on the north end of Ten Thousand Islands in the Everglades. The Census has the population at 391. It is joined to Everglades City by a man made causeway.
Wiki includes the following history about Chokoloskee:
Edgar Watson showed up in the Chokoloskee Bay country in the early 1880s. He had supposedly gotten into trouble in Columbia County in northern Florida, to which his parents had migrated sometime after 1870, and had then gone out to the Indian territory (later known as the Oklahoma Territory) where he allegedly killed Belle Starr, herself allegedly an outlaw. He then returned to Florida and killed a man in Arcadia, apparently in self-defense. After that Ed Watson moved to the Ten Thousand Islands area, then part of Monroe County, where he bought a claim on the Chatham Bend River and began raising vegetables.
On a trip to Key West, Watson got into an argument with Adolphus Santini (an early Chokoloskee settler) and tried to cut his throat. Santini survived, but the incident cost Watson $900. After that Watson bought a claim on the Lost Man's River, also in Monroe County. A man named Tucker soon squatted on the claim and would not leave. Eventually Tucker and his nephew were found murdered, and suspicion fell on Watson. After that Watson went back to Fort White, Columbia County. While there he again became involved with bad company, and came under suspicion in the deaths of two men.
There are dozens of air boats in Everglades City and Chokoloskee. They take tourists for noisy rides down mangrove tunnels and grass flats.
The business model here has changed from commercial fishing to rum smuggling to marijuana importation to tourism over the last 100 years. Our Captain, tells us that he is the 5th generation born here.
In the 1980s, these remote population centers became notorious as drug smuggling hubs. A local source admits that the towns have lots of "felons" who received a "higher education" at the federal penitentiary because of the war on drugs.
in 1983, more than 300 were arrested in Everglades City and nearby Chokoloskee. That's probably close to the entire male population. It was also a center for rum smuggling during the prohibition era. "There are two expression that no one uses in this town anymore," the Miami News quoted an unidentified resident as saying. "One is that this town is going to pot. The second is that we are waiting for our ship to come in."
We spend two nights here and move on to Lake Griffin near Leesburg. The GPS routes us straight up US 27, a huge blunder involving seemingly endless traffic lights.