Book Now!

The Conch Connection

Secrets You Don't Know About Historic Key West

Updated on: Feb 24, 2021 7:40:20 PM

Key West is positively a real-life Shangri La! The tiny island is approximately 4 miles long and 2 miles wide however, it can keep a “history nut” occupied for hours, days…..even weeks! Whether your interest is in the original settlers and inhabitants, politics, nature, architecture, famous residents or visitors including poets, writers, singers or pirates and treasures, marine life or quirky culture, Key West will have something to pique your interest.

Early native island residents named Key West “Cayo Hueso”, which translated means “Island of Bones”, or more commonly referred to as “Bone Island”. The island was actually used as a giant graveyard and was scattered with human bones!

The original inhabitants were believed to be Indians who had developed villages and structures on the island. The Calusa’s who were known to be peaceful, defended their territory when Juan Ponce De Leon “discovered” the new land in 1513. De Leon’s discovery did lead to the 16th century Spanish invasion, though he was not successful in conquering the Indians.  Here's a fantastic article detailing some of DeLeon's history in the New World.  

A fabulous place for seeking historical details, as experienced and perceived in early Key West life, may be found by reading "A Sketch of Key West, Florida” by Walter C. Maloney. Originally penned in 1876,sketchofhistoryo00malo_0007 this 88 page essay is filled with fascinating details of what was at the time, the largest city in Florida.

Photo Credit: Floridiana Facsimilie Reprint by University of Florida Press, Gainesville 1968








“Key West; The Old and The New” by Jefferson Beale Browne

Published in 1912, this version, eloquently and respectfully written was begun as a more detailed version of Walter Maloney’s documentation of Key West in their era.  An archived copy of his work can be found HERE


Key West has been a favorite destination for famous people throughout history including; Ulysses S. Grant, Grover Cleveland, William Taft, Calvin Coolidge, Harry Truman, John F. Kennedy, Dwight D. Eisenhower and post White House visitors were: Jimmy Carter, Bill Clinton and George Bush.

Things to do in Key West

Other famous residents and visitors have included Ernest Hemingway, Tennessee Williams, Calvin Klein, Kelly McGillis,  Jimmy Buffet, David Allen Coe, Truman Capote,  John James Audubon, Mel Fisher,  Robert Frost  and Kenny Chesney….. among others.


Key West is littered with museums for every imaginable historic interest.  Below are just a few of the many that you will find.  Some  are a bit more elusive than others, but are none the less worthy of investigation.

1884 Cartograph of Key West

Video Credit: Bravura Media Company


During and following the war in Cuba, many fled to America’s southernmost city. The Cuban influence can be easily seen in the local culture, cuisine, art, landmarks, music and cigars. Cayo Hueso Y Habana Historeum is a great place to begin your Cuban History Hunt…. but be certain to leave plenty of time, and appetite to enjoy a few of the bevy of tantalizing dining options available. Many restaurants have some historic importance, as well.


Some additional Key West fun facts and history hunter’s challenges include locating or visiting;

  • The birthplace of Pan American Airlines
  • The oldest restaurant, established in 1909
  • The oldest island bar
  • The first known island church/place of worship
  • Pirate wrecks
  • The resting place of the cemetery’s first guest
  • Visit in February during the annual Civil War Heritage Days

Read, research and prepare for an exciting adventure….. then book your transportation with Key West Express!

Make Your Own History Book Now

Hero Image Photo Credit: Flip Schulke, Public domain, via Wikimedia Commons

Topics: Insider, Museums, Attractions, Activities, Walking Distance, Old-Town, Tours, Information, Beach, Kids

Have something to say? Comment below!!

Subscribe Here!

Recent Posts