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Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

The Best Songs about Key West Ever Made

The Best Songs about Key West Ever Made

December 30th, 2020 | Bars & Nightlife

Whether you’re traveling here soon, call our island city home, or are simply dreaming of a beach vacation, we’ve designed a playlist of Key West songs that capture the essence of our sunny shores. There are countless tracks about the Keys (check out our Quintessential Key West Playlist), but we’ve narrowed it down to the best of the best. From beachy tunes to much loved anthems, here are some of the best songs about Key West ever made.

We've compiled the best Key West songs into a Spotify playlist! Follow the link to hear what we've been listening to.

“Magic” by Kenny Chesney

Although never explicitly mentioning Key West, Kenny Chesney’s lyrics about a magical destination leave little to the imagination. The country crooner transports you to Keys with lyrics “I believe there is magic here...In the music that drifts out on the street, It’s in the barflies drinking their beer..It’s lazy days with Hemingway.” The song is a departure from Chesney’s signature style and sound (“Magic” features steel drum, piano, and saxophone), but the tune will make you want to grab a drink and kick back. Chesney also cemented his love for Key West when he featured the Half Shell Raw Bar on the cover of his hit single “When I See This Bar.” iTunes | Amazon | Spotify

“Key West (Philosopher Pirate)” by Bob Dylan

Bob Dylan certainly doesn’t come to mind when thinking of Key West, but the legendary singer-songwriter recently immortalized the city in a 9:35-minute song, titled “Key West (Philosopher Pirate)”. As it turns out, Dylan’s connection to Key West goes back decades! The late Captain Tony Tarracino said Dylan would visit his saloon on Greene Street. “Key West (Philosopher Pirate)” is featured on “Rough and Rowdy Ways,” the artist’s 39th studio album, released earlier this year. The accordion-heavy song lyricizes Key West as “the enchanted land”, “land of light”, and the “gateway key to innocence and purity,” while also mentioning famous landmarks like Bayview Park, Mallory Square and the Truman Little White House.  iTunes | Amazon | Spotify

“Tin Cup Chalice” by Jimmy Buffet

Jimmy Buffet wrote the lyrics for ‘Tin Cup Chalice’ while sitting at Mallory Square, explaining, "This was my first Key West song. I was running from a bad marriage and a trail of debt, and wound up at the end of America. Nobody cared about either there, and they took the time to applaud the sunset at the end of the day." While Buffet certainly captures Key West’s care-free attitude with this sentiment, his lyrics further convey the island state-of-mind: “I want to go back to the island, Where the shrimp boats tie up to the pilin', Give me oysters and beer for dinner every day of the year, And I'll feel fine, I'll feel fine.” Just like Dylan, Buffet was also a fan of Captain Tony’s Saloon. The pub was featured in his tune, “Last Mango in Paris”. iTunes | Amazon | Spotify

“Key West is the Best” by Steve Tolliver

Named ‘Songwriter of the Year’ by the Trop Rock Music Association, Steve Tolliver’s ‘Key West is the Best’ is an ode to everything we love about the place. He sings of coral reefs, turquoise water, and even seeing Michael McCloud perform live at the Schooner Wharf Bar! Being an experienced boater himself, Tolliver much prefers the “countless bars and come-as-you-are down on Duval Street” to destinations like Havana, Antigua, and St. Barts. iTunes | Amazon | Spotify

“Drunk on Mallory Square” by Dani Hoy

While many songwriters sing of the magic or ‘one human family’ of Key West, a booze fueled ditty about a night on Mallory Square may be all we need. Local singer-songwriter Dani Hoy does just that in “Drunk on Mallory Square”. Howling at the moon, paying a visit to Hog’s Breath Saloon, following the chickens, drinking whiskey, beer, and rum punch, just to “get up the next day and do it again” is all too relatable for many. iTunes | Amazon | Spotify

More tunes we love:

“Key West Heart” by Hugo Duarte

“Where the Gulf Meets the Ocean” by John Frinzi

“Meet Me in the Keys” by Howard Livingston & Mile Marker 24

“Conch Republic Song” by Michael McCloud

“Cayo Hueso” by Rob Mehl

“Everyone Matters (One Human Family)” by Don Middlebrook

“Laid Back and Key Wasted” by Jim Morris

“Key West Time” by Jesse Rice

“The Florida Keys Song” by Gerd Rube

“Always Saturday Night” by Thom Shepherd

“Key West Address” by James T. Slater

“I Moved to Paradise” by Yankee Jack


Learn more about everything Key West has to offer by visiting The Gates Key West Blog, which highlights the island’s greatest assets. Stay and save! Choose from our best rates and special offers when you book direct with The Gates Hotel, a Conde Nast award-winning Key West destination.