Discover the Secrets of Historic Key West
Key West is known for its beautiful sunsets, colorful architecture and laid-back island lifestyle, but beneath its tropical charm lies a fascinating history that spans centuries. From Native American settlements and Spanish explorers to literary legends, presidents and treasure hunters, the island has countless stories waiting to be discovered.
Whether you're a history enthusiast or simply curious about the island beyond Duval Street, Historic Key West offers a remarkable journey through Florida's past.
Why Is Key West Called Cayo Hueso?
Long before Key West became a popular vacation destination, it was known as Cayo Hueso, Spanish for "Bone Island."
When early Spanish explorers arrived, they found the island scattered with human bones believed to have been left behind by Native American burial grounds. The name remained long before the English translation evolved into what we know today as Key West.
The island's earliest known inhabitants were the Calusa Indians, who built villages throughout Southwest Florida and the Florida Keys. Although Juan Ponce de León arrived in 1513, the Calusa fiercely defended their homeland, and Spanish settlement efforts faced significant resistance.
Photo Credit: Floridiana Facsimilie Reprint by University of Florida Press, Gainesville 1968
Step Back in Time
For visitors wanting a deeper understanding of Key West's early history, one of the most fascinating historical accounts is "A Sketch of Key West, Florida" by Walter C. Maloney.
Originally published in 1876, the book provides a firsthand look at daily life during a time when Key West was Florida's largest city. It remains one of the most detailed historical records of the island's early years.
Another excellent read is "Key West: The Old and the New" by Jefferson Beale Browne, published in 1912. Building upon Maloney's work, Browne documents the island's people, architecture, economy and unique culture during the early twentieth century.
Famous Visitors and Residents
Throughout its history, Key West has welcomed presidents, artists, authors, musicians and adventurers seeking inspiration from the island's unique atmosphere.
Several U.S. presidents—including Harry S. Truman, Dwight D. Eisenhower and John F. Kennedy—visited Key West during their presidencies, helping cement the island's place in American history.
The island has also attracted many notable writers, performers and public figures, including:
- Ernest Hemingway
- Tennessee Williams
- Truman Capote
- Robert Frost
- Jimmy Buffett
- Kenny Chesney
- John James Audubon
- Mel Fisher
- Calvin Klein
- Kelly McGillis
- David Allan Coe
If you'd like to explore more of the island beyond its history, check out our guide to Things to Do in Key West.
Explore Key West's Museums
One of the best ways to experience the island's history is by visiting its outstanding museums. Each tells a different chapter of Key West's remarkable story.
Some visitor favorites include:
- Key West Art & Historical Society at the Custom House Museum
- Mel Fisher Maritime Museum
- Truman Little White House
- Ernest Hemingway Home & Museum
- Key West Lighthouse & Keeper's Quarters Museum
- Key West Shipwreck Treasure Museum
- Fort East Martello Museum
- Key West Firehouse Museum
- Heritage House Museum
- Oldest House Museum & Garden
- Florida Keys Eco-Discovery Center
- Fort Zachary Taylor Historic State Park
- Dry Tortugas National Park and Fort Jefferson
- Key West Cemetery
- Florida Keys Museum of Natural History
- Cayo Hueso y Habana Historeum
- Lofton B. Sands African-Bahamian Museum
- Flagler Station Oversea Railway Historeum
Whether you're interested in maritime history, military forts, literary icons or local culture, there's a museum for every interest.
Discover Key West's Cuban Heritage
Cuba has played a major role in shaping Key West's identity.
During the nineteenth century, thousands of Cuban immigrants settled on the island, bringing traditions that still influence local cuisine, music, architecture and cigar making today.
One of the best places to learn about this rich heritage is the Cayo Hueso y Habana Historeum, which explores the close relationship between Key West and Havana.
After exploring the exhibits, take time to enjoy authentic Cuban cuisine, fresh Cuban coffee or visit one of the island's traditional cigar shops.
1884 Cartograph of Key West
Video Credit: Bravura Media Company
Hidden Historic Treasures
History lovers will discover countless hidden gems throughout Key West. Keep an eye out for:
- The birthplace of Pan American Airways
- The island's oldest restaurant, established in 1909
- Historic waterfront bars that have welcomed generations of visitors
- Sloppy Joe's
- Captain Tony's
- Pepe's Cafe (Key West's oldest - 1909)
- The first churches built on the island
- Pirate legends and shipwreck stories
- The fascinating Key West Cemetery
- Historic homes tucked along Old Town's quiet streets
Many of these landmarks are within walking distance of one another, making Historic Key West one of Florida's most enjoyable places to explore on foot.
Experience Historic Key West with Key West Express
Traveling aboard the Key West Express places you just minutes from the Historic Seaport, making it easy to begin exploring the island's rich history shortly after arriving. Historic Key West isn't simply a collection of landmarks—it's a living story waiting to be explored one street, museum and waterfront at a time.
Spend the day visiting museums, discovering historic landmarks, strolling Old Town's charming streets and uncovering stories that have shaped one of America's most unique destinations.
Whether it's your first visit or your tenth, there's always another chapter of Key West's history waiting to be discovered.
Frequently Asked Questions
Why is Key West called Cayo Hueso?
Spanish explorers named the island Cayo Hueso, meaning "Bone Island," after discovering human remains believed to be from Native American burial grounds.
Who were the first inhabitants of Key West?
The Calusa people were among the earliest known inhabitants of the region before European exploration.
What is the oldest part of Key West?
Old Town Key West contains many of the island's oldest homes, historic buildings and cultural landmarks.
What are the best museums in Key West?
Popular museums include the Custom House Museum, Mel Fisher Maritime Museum, Truman Little White House, Hemingway Home and the Key West Lighthouse Museum.
Why is Cuban culture so important in Key West?
Cuban immigrants helped shape the island's history, influencing its architecture, cuisine, cigar industry, music and traditions.
Can you walk to most historic attractions?
Yes. Many of Key West's museums, landmarks and historic sites are located within easy walking distance in Old Town.
Where did Ernest Hemingway live in Key West?
Ernest Hemingway lived at the Hemingway Home & Museum on Whitehead Street, one of the island's most visited historic attractions.
What is the Key West Cemetery known for?
The cemetery is famous for its unique epitaphs, historic graves and fascinating stories dating back to the nineteenth century.
Is Historic Key West family-friendly?
Absolutely. Museums, historic homes, parks and walking tours provide enjoyable experiences for visitors of all ages.
What's the best way to visit Historic Key West?
Travel aboard the Key West Express, arrive near the Historic Seaport and explore Old Town's rich history on foot.
Hero Image Photo Credit: Flip Schulke, Public domain, via Wikimedia Commons
