Off the Beaten Path in Key West

Free Off the Beaten Path in Key West with Roamee Pro

Roamee Pro, also known as Roamee, offers a free off-the-beaten-path walking tour route in Key West. The audio walking tour can include stops such as Hemingway Home and Museum — Ernest Hemingway purchased this 1851 Spanish colonial house in 1931 for $8,000, and it was the first residence in Key West to have a swimming pool, which cost $20,000 to build during the Great Depression. Today approximately 60 polydactyl (six-toed) cats roam the property, believed to be descendants of Hemingway's original cat Snow White, gifted by a ship captain. The second-floor writing studio where Hemingway worked each morning overlooks the lush tropical gardens and the pool house., Mallory Square — Every evening, roughly two hours before sunset, this waterfront plaza transforms into an open-air festival known as the Sunset Celebration, a tradition dating back to the counterculture era of the 1960s. Street performers including sword swallowers, trained house cats, and tightrope walkers entertain crowds of up to several thousand, while the unobstructed western horizon over the Gulf of Mexico produces some of the most vivid sunsets in the Florida Keys. The square also houses the Key West Aquarium, built in 1934 as one of the first open-air aquariums in the United States., Duval Street — Running 1.25 miles from the Gulf of Mexico to the Atlantic Ocean, Duval Street is the only street in America that stretches from sea to shining sea, a claim celebrated by the annual 'Duval Crawl' bar-hopping tradition. Historic stops include Sloppy Joe's Bar, where Hemingway was a regular in the 1930s, and Captain Tony's Saloon, the original Sloppy Joe's location. The street also passes the San Carlos Institute, a Cuban cultural center founded in 1871 that played a role in Cuba's independence movement., plus hidden gems like Fort Zachary Taylor — Constructed between 1845 and 1866, this Civil War-era fort was built on an artificial island and remained a military installation through the Spanish-American War and both World Wars. The fort's beach, protected by a natural reef and shaded by Australian pine trees, is consistently rated the best beach in Key West with superior snorkeling directly from shore over coral formations teeming with tropical fish. and Key West Cemetery — Established in 1847 after a hurricane washed away the original burial ground, this 19-acre cemetery holds approximately 100,000 graves, many in above-ground vaults necessitated by the island's high water table and coral rock substrate. The cemetery is famous for its humorous epitaphs, including the widely quoted 'I Told You I Was Sick,' and features separate sections reflecting the island's diverse Cuban, Bahamian, and Jewish communities..

Use this page as a starting point for a Key West walking tour, a free route, or the Roamee app for Key West. Roamee Pro keeps the route flexible so you can follow the stops, skip ahead, or explore nearby streets at your own pace.

• •Hemingway Home and Museum — Ernest Hemingway purchased this 1851 Spanish colonial house in 1931 for $8,000, and it was the first residence in Key West to have a swimming pool, which cost $20,000 to build during the Great Depression. Today approximately 60 polydactyl (six-toed) cats roam the property, believed to be descendants of Hemingway's original cat Snow White, gifted by a ship captain. The second-floor writing studio where Hemingway worked each morning overlooks the lush tropical gardens and the pool house.
• •Mallory Square — Every evening, roughly two hours before sunset, this waterfront plaza transforms into an open-air festival known as the Sunset Celebration, a tradition dating back to the counterculture era of the 1960s. Street performers including sword swallowers, trained house cats, and tightrope walkers entertain crowds of up to several thousand, while the unobstructed western horizon over the Gulf of Mexico produces some of the most vivid sunsets in the Florida Keys. The square also houses the Key West Aquarium, built in 1934 as one of the first open-air aquariums in the United States.
• •Duval Street — Running 1.25 miles from the Gulf of Mexico to the Atlantic Ocean, Duval Street is the only street in America that stretches from sea to shining sea, a claim celebrated by the annual 'Duval Crawl' bar-hopping tradition. Historic stops include Sloppy Joe's Bar, where Hemingway was a regular in the 1930s, and Captain Tony's Saloon, the original Sloppy Joe's location. The street also passes the San Carlos Institute, a Cuban cultural center founded in 1871 that played a role in Cuba's independence movement.
• •Southernmost Point — This painted concrete buoy marking latitude 24 degrees 32 minutes 43 seconds North was installed in 1983 and has become one of the most photographed landmarks in Florida, with visitors often waiting in line for 30 minutes or more. The marker stands at the corner of Whitehead and South Streets, and while it is not technically the southernmost land (that distinction belongs to a nearby naval installation), it remains the southernmost publicly accessible point in the continental United States.

• •Fort Zachary Taylor — Constructed between 1845 and 1866, this Civil War-era fort was built on an artificial island and remained a military installation through the Spanish-American War and both World Wars. The fort's beach, protected by a natural reef and shaded by Australian pine trees, is consistently rated the best beach in Key West with superior snorkeling directly from shore over coral formations teeming with tropical fish.
• •Key West Cemetery — Established in 1847 after a hurricane washed away the original burial ground, this 19-acre cemetery holds approximately 100,000 graves, many in above-ground vaults necessitated by the island's high water table and coral rock substrate. The cemetery is famous for its humorous epitaphs, including the widely quoted 'I Told You I Was Sick,' and features separate sections reflecting the island's diverse Cuban, Bahamian, and Jewish communities.