Legends of Key West, Florida Walking Tour

Key West is well known for pristine beaches and a rowdy nightlife, but there is far more to the majestic island than just sand, surf and suds. The southernmost tip of the continental United States has attracted a myriad of artists and writers over the years and they have left their respective marks on Key West culture. Explore the literary and artistic side of the "Conch Republic" and discover the city's cultural treasures along the way.

Ernest Hemingway fell in love with both the natural beauty of the island and the atmosphere at Hog's Breath Saloon. The accomplished author spent many hours courting both a strong glass of whiskey and his second wife inside the popular Duval Street bar. Hemingway lived and wrote at his Key West residence amid his family of cats. The now famous "Hemingway Cats" have grown to a clan of nearly 100 and pounce at your feet as you tour the grounds. Many of the cats still bear the "six-toe" abnormality inherited from the writer's first tomcat, given to him by a local boat captain.

Hemingway wrote the novel, Farewell to Arms while nestled among the courtyard palm trees and sipping whiskey on cool south Florida mornings. You will notice the trophies from Hemingway's many African safaris mounted on the wall or stuffed and free-standing in the study. The property also features the first swimming pool built in Key West. Look for the penny Hemingway pressed into the concrete near the pool entrance as an expression of his disdain for the cost of building the swimming pool. "Here, take the last penny I've got," the writer reportedly exclaimed as he pushed the copper coin into the still wet cement.

907 Whitehead Street
Key West, FL 33040
United States
24.330447 N 81.480197 W

The name Jimmy Buffett has become synonymous with Key West. Buffett's flagship Margaritaville restaurant and recording studio are both located in the seat of Monroe County. Buffett has spent many hours drinking Hurricanes and tuning his guitar inside the Shrimp Boat Sound recording studio. While you can't tour the inside of the building, you just might catch a glimpse of the "Trop-Rock" crooner entering or exiting the studio. The best possible vantage point for sightings of Buffet or any of his celebrity musician buddies would be along the edge of the dock next to the property. The singer has mere steps to walk after pulling his boat ashore and reaching the back door of the studio.

On any given day, excited fans and would be singing stars can be seen huddled near the entrance to the studio with a camera in hand. If you get lucky, you might hear Buffett and friends warming up or trying out a new tune. Even though Jimmy Buffett was born in Alabama, the "Conch Republic" has made his their favorite native son, with the lyrics to the hit song Margaritaville or the cult favorite Laid Back and Key Wasted known by all who live on the island of Key West. The studio does not have a public address listed or any visible numbers on the building. The coordinates and address listed in this guide are to the Schooner Wolf boat slip located adjacent to the studio, which was built on the marina patio.

402 Applerouth Lane #2A
Key West, Florida 33040
United States
24.331655 N 81.481090 W

Key West Memorial Sculpture Garden features 36 bronze busts and statues celebrating both famous residents and infamous notables who once called the "Conch Republic" home. Enter the sculpture garden via the Waterfront Playhouse walkway, adjacent to Mallory Square. Walk back in time as you meander through the garden and discover the characters who formed the early community of Key West as well as modern day mavens and marvels who keep the unconventional island spirit alive and thriving. Master sculptor, James Mastin created all of the statues and busts entirely by hand. The Wreckers sculpture is the largest in the garden, measuring 25 feet tall and 18 feet long. While the creation does not depict any known individual it does convey the likeness of brave men who raced to save both cargo and lives from the many shipwrecks off the coast of Key West during the 1800's.

310 Wall Street
Key West, Florida 33040
United States
24.333239 N 81.462534 W

President Harry Truman spent so much time at his Key West vacation home that the mansion was dubbed the "Little White House." President Truman retreated to the warm tropical climate for 175 days during his presidency. Although the historic home is most known for the former Commander in Chief's occupancy, the structure was intertwined with American history long before it gained the "Little White House" moniker. President Taft vacationed at the home in 1911 and Inventor Thomas Edison spent six months on the property in 1918 while he was developing nearly 50 new weapons to be used in the World War I.

President Truman and his Joint Chiefs of Staff created a plan to combine the Department of War and the Department of the Navy into a new division - the Department of Defense while lodging at the "Little White House." Although the Key West home was supposed to be used as a refuge from the stressful daily workings of the presidency, Truman signed scores of important documents into law while rejuvenating in the Florida Keys. President Dwight Eisenhower also vacationed at the "Little White House" and convalesced during the winter of 1955 after suffering from a heart attack. President Kennedy met with British Prime Minister Macmillan inside the historic home, just a few weeks before the Bay of Pigs operation. Presidents Jimmy Carter and Bill Clinton also vacationed on the property during their terms in office. Walk in the footsteps of former world leaders as you tour the grounds and historic structures.

111 Front Street
Key West, Florida 33040
United States
24.331838 N 81.482358 W

Become an official "Parrot Head" for an afternoon at Jimmy Buffett's original Margaritaville restaurant. See what a cheeseburger in paradise really tastes like, and you can even wash it down with a signature Buffett frozen concoction. If you happen into the eatery at the right time, you might get to hang out with the singer, or at least catch an impromptu jam session. Even if celebrity sightings aren't in the cards for you, that will not damper the great time to be had in Margaritaville. Live musical performances, made in Key West merchandise and Buffett themed souvenirs are on tap daily at the Duval Street restaurant. Arrive early if you plan on getting a seat on a Saturday night.

500 Duval Street
Key West, Florida 33040
United States
24.332022 N 81.481072 W

John James Audubon's home and studio were turned into a museum several decades after the naturalist lived on the island studying and drawing the flamingo. Explore the historic home, tropical gardens and art gallery displaying images of tropical birds captured forever by the artist's brush and oil paint. John James Audubon first visited the island in 1832. Before leaving the tropical paradise, he spent days in the home's courtyard sketching 18 "new" birds for his Birds of America project. After listening to a bit of Audubon and property history, you embark upon an unguided tour through the home and garden pathways. Luxurious antique furnishings fill the home and colorful Orchids and Bromeliads dot the exterior landscape. Swing past the gift shop to browse reprints of Audubon's artwork where you can purchase a souvenir of the experience and display a little taste of Key West in your own home.

205 Whitehead Street
Key West, Florida 33040
United States
24.332991 N 81.482166 W

Poet Robert Frost wrote some of his most famous works while relaxing at his cottage in Key West. The property, also known as Heritage House was a frequent gathering spot for notables such as Tennessee Williams, Gloria Swanson and Thornton Wilder. Over 200 years of Key West history is on display inside the main house and Frost cottage. Museum displays of artwork, literary creations and handmade furnishings are scattered about the structures. The poet wintered in the cottage for sixteen years, soaking up the tropical warmth and laid back elegance of the Florida Keys.

A prominent Key West family, the Porters built the home and cottage in 1934. Jean Porter opened the home for tours and historic displays while writing the novel, "Conch Smiles" about her experiences on the island. She was also instrumental in preserving other historic buildings in the "Old Town" district of Key West, including the Audubon House.

410 Caroline Street
Key West, Florida 33040
United States
24.557502 N 81.805127 W

Directions to Starting Point

Take a taxi to Truman Avenue and ride until you see Whitehead Street and turn right. Travel straight one block and Hemingway's Home and Museum will be the at the edge of the last turn on your right. If walking, Whitehead Street is one block north of Duval Street. The Key West Conch Train makes a loop around the "Old Town" district from Front Street to Mallory Square. You can catch the train at the Front Street Depot, Flagler Street Station or Roosevelt Boulevard and disembark at the main station depot at the corner of Front and Duval Street and walk two blocks north to the Hemingway House and Museum.

Tour Distance

Starting Point - The distance from Hemingway House to Jimmy Buffett's Shrimp Boat Sound Recording Studio is .3 miles and takes approximately six minutes to walk. The distance to point 3, Key West Memorial Sculpture Garden is .4 miles and takes approximately 7 minutes to walk. You will walk .2 miles, taking approximately 3 minutes to arrive at Truman's Little White House. Journey .2 miles further and reach Audubon House in approximately three minutes. The final stop on the tour, Robert Frost Cottage is 522 feet away and will take you about a minute to reach on foot.