KEY WEST,  FLORIDA

By  Mike Miller Updated March 3, 2025

Key West, Florida is about 129 miles southwest of Miami along US Highway 1, the Overseas Highway. 

It is also 106 miles north-northeast of Havana, Cuba as the crow flies. 

Map of the Florida Keys

That sounds pretty close to places you've heard of, but Key West is light years away in culture and history from almost any other place most folks have visited.

The town and island was originally called Cayo Hueso by the Spanish, a term that means "bone key".  Many Key West businesses still use the name.

Vintage Postcard Boca Chica Bridge

When Great Britain took control of Florida in 1763, the Spanish and Native American population of Key West were largely removed to Havana.

When Spain took control back about 20 years later, there was no attempt to resettle the mostly deserted island.

City Hall, Key West, Florida 1876
Flickr/Florida Keys Public Library

It began to be used by Cuban fishermen and loyalist settlers from the Bahamas who had fled the United States after the Revolutionary War.

These early white Bahamian settlers were known as Conchs, pronounced conk, like conk in the head). They began to really populate the Keys in the years after 1830.

MORE ABOUT THE HISTORY OF KEY WEST, FLORIDA

Map of Key West, Florida

This earlier isolation and current end of the road status gives Key West Florida its romantic bohemian flavor today.

Truman's Little Whitehouse

Key West became nationally famous when U.S. President Harry S. Truman made the island city his winter "Whitehouse" after World War Two.

Key Deer on the Way to Key West, Big Pine Key

KEY WEST SECEDES FROM THE UNITED STATES OF AMERICA

The personality of the people of Key West was demonstrated dramatically in 1982 when the citizens decided to leave the USA and founded the Conch Republic.

Flag of the Conch Republic

This action was taken in response to a blockade set up by the Federal Government in Florida City at the Last Chance Saloon.

The blockade was supposedly to search for illegal drugs and immigrants.  It immediately caused a huge 17 mile traffic jam and was hurting the tourism industry.

Read a great account of the entire incident at this link.

THE FOUNDING OF THE CONCH REPUBLIC

Sonny McCoy

One of the interesting characters I knew during my engineering career was Sonny McCoy.  He was an architect and had been Mayor of Key West and Mayor of Monroe County. 

In 1978, while mayor, he waterskiied on a single slalom ski from Key West to Havana.  His trip on September 10, 1978 took six hours and 10 minutes.  Ironically, he passed away on September 10, 2020 at the age of 92.

He was quoted as saying about the trip, "I felt terrible until about 10 miles out of Key West, and for the next 100 miles I was feeling awful."

Duval Street, Key West
Flickr/WildRedHead

The Naval Air Station Key West is a major employer, and conducts year round training for naval aviators.

Key West Custom House

The military presence is one of the reasons Harry Truman chose Key West as the winter White House when he was president.

The Conch Train in Key West

The heart of Key West is Duval Street and its central business district.

This district takes up most of the northwest corner of the island.

Key West Lighthouse
Flickr/Pom'

There are many restaurants here and the famous Sloppy Joe's Bar, the legendary drinking hangout of Ernest Hemingway.

Sloppy Joe's, Hemingway's Hangout

Other major streets are Whitehead, Simonton, Front, Greene, Carolina, Eaton and Truman Avenue.

Hemingway Home

Ernest Hemingway's home is on Whitehead and is open to the public.  You will probably see some descendants of his many six toed cats.

Sloppy Joe's, Hemingway's Hangout

There are hundreds of things to do in Key West. Something always seems to be happening.

Key West Sunset at Mallory Square

A daily event that locals and tourists both love is the evening sunset celebration at Mallory Square.

There are also many great hotels in Key West to serve as your base of operations.  Be forewarned, however:  lodging is very expensive in Key West.

KEY WEST FLORIDA POPULAR ANNUAL EVENTS

Some popular annual events include:

• Key West Race Week - international sailing event – January
• Key West Literary Seminar – January
• Conch Republic Independence Celebration – April 23
• Taste of Key West - April
• Red Ribbon Bed Race – April
• Survivors Party – May
• Queen Mother Pageant – May
• PrideFest – June
• Cuban-American Heritage Festival – June
• Hemingway Days Festival – July
• WomenFest – September
• Fantasy Fest – October
• Goombay Celebration – October
• Robert the Enchanted Doll Day – October 24
• Boat and Holiday Parade – December
• Pirates in Paradise Festival (Pirate Fest) November 26 - Dec 5

Robert the Doll

THINGS TO DO IN KEY WEST, FLORIDA

Key West Butterfly and Nature Conservatory
1316 Duval St, Key West, FL 33040 | (305) 296-2988

The Key West Butterfly and Nature Conservatory is a magical place filled with beautiful butterflies and tropical birds. We enjoy walking through the lush gardens and seeing the colorful butterflies up close.

Visitors appreciate the peaceful atmosphere and the educational exhibits about butterfly life cycles. The conservatory also features lovely koi ponds and cascading waterfalls.

It's a zen place for families and nature lovers to relax and enjoy the beauty of nature. The friendly staff is always ready to answer questions and provide interesting facts.

Fort Zachary Taylor Historic State Park
601 Howard England Way, Key West, FL 33040 | (305) 292-6713

Fort Zachary Taylor Historic State Park is a Civil War-era fort located near the southern tip of Key West. It’s a fascinating blend of history and natural beauty. We enjoy exploring the historic fort and learning about its role in the Civil War.

Visitors appreciate the beautiful beach and the excellent snorkeling opportunities. The park offers shaded picnic areas and scenic walking trails.

It's an invigorating spot for a day of history, relaxation, and outdoor activities. The well-preserved fort and informative displays make it an educational experience.

Key West Lighthouse and Keeper's Quarters Museum
938 Whitehead St, Key West, FL 33040 | (305) 294-0012

The Key West Lighthouse and Keeper's Quarters Museum offers stunning views and rich history. We enjoy climbing the 88 steps to the top of the lighthouse for panoramic views of Key West.

Visitors appreciate the well-preserved keeper's quarters and the interesting exhibits about lighthouse history. The museum provides insights into the lives of the lighthouse keepers and their families.

It's a great place to learn about maritime history and enjoy the beautiful scenery. The friendly staff and well-maintained grounds make it a pleasant visit.

U.S. Coast Guard Cutter Ingham Maritime Museum
Truman Waterfront Park, Southard St, Key West | (305) 292-5072

The U.S. Coast Guard Cutter Ingham Maritime Museum is a fascinating piece of naval history. We enjoy touring the historic ship and learning about its service during World War II and Vietnam.

Visitors appreciate the well-preserved artifacts and the informative exhibits. The museum provides a unique look at life aboard a Coast Guard cutter.

It's an interesting place for history buffs and military enthusiasts. The knowledgeable guides and interactive displays make it an engaging experience.

Papa’s Pilar Rum Distillery, Hemingway Rum Company
201 Simonton St, Key West, FL 33040 | (305) 414-8754

Papa’s Pilar Rum Distillery, Hemingway Rum Company is a great place to learn about the art of rum making. We enjoy the guided tours that take you through the distilling process and the history of Hemingway's connection to rum.

Visitors appreciate the tasting room where they can sample the award-winning rums. The distillery's rustic decor and friendly staff create a welcoming atmosphere.

It's a fun place for rum enthusiasts and those interested in Key West's cultural heritage. The informative tour and delicious rum make for an enjoyable experience.

Smathers Beach
2601 S Roosevelt Blvd, Key West, FL 33040 | (305) 809-3700

Smathers Beach is Key West's largest public beach, offering a perfect spot for relaxation and water activities. We enjoy the soft white sand and the clear turquoise waters.

Visitors appreciate the amenities, including volleyball courts, picnic areas, and water sports rentals. The beach is great for swimming, sunbathing, and snorkeling.

It's a wonderful place for a family outing or a day of fun in the sun. The beautiful scenery and well-maintained facilities make it a favorite destination.

Sloppy Joe's Bar
201 Duval St, Key West, FL 33040 | (305) 294-5717

Sloppy Joe's Bar, pictured and discussed earlier, is a legendary watering hole with a rich history dating back to 1933. We enjoy the lively atmosphere and the live music that fills the air.

Visitors appreciate the famous Sloppy Joe sandwiches and the wide selection of drinks. The bar is a great place to soak up the local culture and enjoy a fun night out.

It's also known for its connection to Ernest Hemingway, who was a regular patron. The friendly staff and vibrant crowd make every visit enjoyable.

Naval Air Station Key West
Boca Chica Field, Key West, FL 33040 | (305) 293-3333

Naval Air Station Key West, discussed earlier, is a vital military installation known for its strategic training operations. Visitors appreciate the opportunity to see military aircraft and the base's beautiful coastal location. The station provides crucial training for Navy pilots and is an important part of the Key West community.

Audubon House & Tropical Gardens
205 Whitehead St, Key West, FL 33040 | (305) 294-2116

The Audubon House & Tropical Gardens in Key West is a charming historical site and botanical garden built by Captain John Huling Geiger in the 1840s as a residence for his family, who lived there for more than a century.

We enjoy exploring the beautifully restored 19th-century home and learning about John James Audubon’s 1832 visit to the Keys. You can view some of his artwork within the Geiger home or visit the Gift Shop for one-of-a-kind finds.

Visitors appreciate the lush tropical gardens filled with exotic plants and orchids. The guided tours provide fascinating insights into local history and Audubon’s life. 

To see even more interesting places in Key West, click on the link towards the bottom of the page for my FLORIDA KEYS TRAVEL GUIDE.

KEY WEST WEBCAM

Click icon for real time streaming video of Key West,
then be patient.  It sometimes takes a while to load.

Key West is the end of the Keys island chain.  Here is a guide that tells you all about the rest of the Keys:

FLORIDA KEYS TRAVEL GUIDE