Nightlife Tour in Key West

Free Nightlife Tour in Key West with Roamee Pro

Roamee Pro, also known as Roamee, offers a free nightlife tour route in Key West. The audio walking tour can include stops such as 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., 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.

• •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.

• ›Match the local clock. In many cities dinner is 9pm and bars don't fill until midnight — show up at 8 and you'll drink alone.
• ›Build the night as an arc: a rooftop or viewpoint near Mallory Square at sunset, dinner, then bars and live music as the night gets later and looser.
• ›Keep some cash and note the last metro or tram time — late-night transport gaps are where good nights turn into expensive cab rides.
• ›Ask a bartender where they go after their shift. It's the single best nightlife tip in any city and it's free.
• ›Stick with your group, watch your drink, and trust your read on a place — the right move when somewhere feels off is simply to leave.