Key West

About two decades ago, when Jimmy Buffett visited Honolulu, he in the process helped another artist make his own eventual connection to Key West. In the early 2000s, ukulele player Jake Shimabukuro was performing in a local surf shop when Buffett stopped by and, impressed, left a note encouraging the young musician to attend an upcoming concert, where he would actually end up playing live.

Things can feel like a bit of a circus heading into the high season in Key West. Naturally, two artists are embracing the concept of clowns for one big visual impact. Illustrator Kristyn LaMoia and performer Nina Pilar are teaming up for a night of new work and shows on Feb. 28 titled “Fancy Clown” upstairs General Horseplay at HiNote Bar.

When artist ransome outlined his ideas for a Key West residency in 2023 at The Studios of Key West, he wanted to examine the history of Bahama Village, blocks away from his temporary home, as it was shaped by its original inhabitants. Now, the painter and collage artist is presenting these visual works at his “Ghost in Bahama Village” exhibit, which will run through February in the Sanger Gallery.

Described as bringing a vibrancy to her folk-pop songs, musician Rachael Sage is a six-time Independent Music Award Winner, who is taking her uplifting performances to the southernmost city.

There is evolution in Tom Flip’s black and white styled portraits. The photographer and bartender knows that his popular twice-a-decade portraits demonstrate more than just him taking good pictures. These portraits are a way for the inhabitants of Key West and beyond to look back at who they were as an island at one moment in time.

Key West comes alive with the nationally recognized Mile 0 Fest that brings Red Dirt and Americana music to iconic venues across the island. This has rapidly become a huge draw for tourists, selling an overwhelming majority of tickets to visitors. The festival is produced by Mako Moco, which puts on shows year-round in other states. 

The "Red High Heel Shoe Drop" at Bourbon St. Pub in Key West by owner Joe Schroeder saw female impersonator "Sushi" lowered in an oversized shoe on New Year's Eve for 25 years. An event that was seen by tens of thousands and broadcast to even more.

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