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Tucked Between Everglades National Park and the Ten Thousand Islands, Little Chokoloskee is Considered one of Florida's Last Frontiers
Sitting between Everglades National Park and the Ten Thousand Islands on Florida's far southwestern coast, remote Chokoloskee sits on equally remote, one square mile Chokoloskee Island. The town has been a tomato field, a sugar cane patch and an outlaw hideout. It was essentially its own little world until the 1950s when the Tamiami Trail connected neighboring Everglades City to the rest of Florida.
Today, Chokoloskee is still considered one of Florida's last frontiers. Homes cover the island, but they are not packed together like sardines. There are condos, modest manufactured homes and beautiful waterfront residences, as well as a couple of RV resorts with active marinas. Despite its "of the map" location, Chokoloskee is a tourist and sport fishing destination, with several outfitters offering Gulf and Everglades fishing trips. Most residents are crab fishermen. The historic, red Smallwood Store was owned and operated by the town's first postmaster and is now a rustic museum with a wooden floor and artifacts from Chokoloskee's rural history. Nearly all services and supplies are found five miles away in Everglades City, which is only accessible via boat or the causeway named Smallwood Drive.
Population: 1,200 (city proper)
Percentage of Population Age 45 or Better: 70%
Cost of Living: 6% below the national average
Median Home Price: $390,000
Climate: Summer temperatures are in the 80s and 90s, and winter temperatures are in the 40s, 50s and 60s. On average, the area receives 53 inches of rain per year.
At Least One Hospital Accepts Medicare Patients? No
At Least One Hospital Accredited by Joint Commission? No. The closest hospital, which is accredited, is in Naples, 28 miles away.
Crime Rate: Below the national average
Public Library: No
Public Transit: No
Political Leanings: Conservative
Is Florida Considered Tax Friendly for Retirement? Yes
Cons: Hurriance Irma caused significant damage in 2017 and Ian in 2022 brought flooding. Hurricane Donna did the same in 1960, as did Andrew in 1992 and Wilma in 2005. More will do damage in the future.
Notes: Thanks to the mounds built by the Calusa Indians in pre-Columbian times, Chokoloskee is about 18 feet above sea level.
Recommended as a Retirement Spot? Maybe. The remote location, distance to a hospital and hurricane threat should be considered.
Sticking out into Hurricane Alley, Florida was a land no nation seemed to want. Ruled successively by Spain, France, England, and the Confederate States of America, the state had a backwater reputation. Other than St. Augustine and Pensacola, there were few cities. The area was rural and populated by frontier farmers.
In the late-1800s, changes came when railroads began chugging down both coasts. Industrialist Henry Flagler's Florida Easy Coast Railway even made it all the way to Key West. The Great Florida Land Boom, the build-up to World War II, and the space industry also helped turn Florida into one of the nation's most populous states. In 1900, there were about 500,000 residents. Today, there are more than 20 million, almost 351 people per square mile.
Why do people keep coming? Tourism marketing is one reason. Annually, millions visit Orlando's theme parks and the state's 663 miles of white sand beaches. Taxes generated by the billion dollar vacation industry allow Florida to prosper without a personal income tax. Budget-sensitive retirees have flocked to its cities and shorelines.
If you can ignore the hurricanes, the state's climate is relatively mild. Only five other states are sunnier. Florida's system of state universities and community colleges is sizable, and its big cities are meccas for culture and the arts. Sarasota is a good example. Its Ringling Museum Complex contains internationally known art museum, a circus museum, an historic theater, and a 66-acre garden. Museums near Orlando range from a Zora Neale Hurston gallery to a Madame Tussauds.
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