Family admires vintage diving helmets in a well-lit museum exhibit.

Museums & Historic Sites

History here doesn’t hide—it strolls the streets, sails the waters, and lingers in lighthouses, forts, and railways. Museums and historic sites across the Florida Keys tell stories of shipwrecks, pioneers, and a railroad that once seemed impossible. Wander through homes of famous writers, climb old fort walls, or step into tiny museums bursting with artifacts. Each stop layers new depth onto the turquoise backdrop. These listings will guide you to the places where past and present meet—sometimes quirky, often surprising, always unforgettable.

Fred the Tree Florida Keys

Fred the Tree: The Florida Keys’ ‘Celebri-Tree’

Fred the Tree — the Florida Keys’ beloved, thriving and resolute “celebri-tree” that grows improbably on the historic Old Seven Mile Bridge — is a movie star.

Cat on a desk in the Hemingway House with a typewriter in a cozy, book-filled study.

Ernest Hemingway

Learn about Ernest Hemingway, his literary reputation and his larger-than-life persona. Credited with establishing Key West as a literary haven, Hemingway left a legacy that remains vibrant today.

Historical marker for African Cemetery at Higgs Beach under palm trees.

Key West African Cemetery

Listed on the National Register of Historic Places, a memorial honors the African Burial Ground at Higgs Beach.

People painting a large mural of a steam train on a bridge.

Florida Keys Over-Sea Railroad

On Jan. 22, 1912, when Ruby Whitlock was eight years old, she watched the arrival of the first train that ever traveled down the Florida Keys Over-Sea Railroad tracks from mainland Florida to Key West.

Group of people in formal attire, some holding hats and flowers, in a vintage photograph. Henry Flagler and his wife.

Henry Flagler: Railroad Visionary

Henry Morrison Flagler never lived in the Florida Keys, but he left a lasting and valuable mark on the island chain.

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USCGC Ingham Maritime Museum

USCGC Ingham Memorial Museum — historic Coast Guard cutter & floating maritime museum in Key West, where legends of service meet immersive history.

Key West

Hellings Curry Museum/ Home of the Key West Woman’s Club

Explore Key West history in a stunning Queen Anne mansion with free guided tours!

Key West

Alex Vega Key West Firehouse Museum

Explore Key West's historic firehouse museum with unique artifacts and fun tours!

Meetings Max
25

Key West

Harry S. Truman Little White House

Presidential museum in Key West.

Weddings Max
300
Meetings Max
50
Total Space
572 sq ft
Largest Room
572 sq ft