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Zac Kellum @ Mac’s Place
Singer songwriter Zac Kellum marks his first appearance at Mac’s, delivering a soulful country sound.
Wynn Taylor
Wynn Taylor takes the stage for a live performance at Rams Head Southernmost.
Rams Head SouthernmostTim Palmieri & Friends
Tim Palmieri returns to Key West with his Funky Friends for a run of shows at The Green Parrot. The lineup features Rob Somerville on sax and vocals, Beau Sasser on bass and keys, and Michelangelo Carubba on drums. The engagement includes multiple sets.
The Green Parrot2026 MCS Supper Club Fundraiser
Celebrate the island community at First Flight Restaurant during the MCS Supper Club, the annual fundraiser benefiting the Montessori Children's School of Key West. Tickets include a curated dinner and dessert menu, live entertainment, and appearances from special guests, plus an open bar featuring house beers and wines. Attire is Island Formal, a chance to bring out outfits that rarely get worn. Childcare is available at the school as a PJ Party, and a Conch Train will shuttle parents between the school and First Flight and back. Keep the evening going with an on-site afterparty with DJ Max following the pinata. An online silent auction will run during the event, with access details to be shared a few days beforehand.
First Flight Island Restaurant & BreweryYour morning shortcut
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