Just a Few Friends, Key West Labor Day Weekend

Just a Few Friends - Key West

Labor Day Weekend | August 29 - September 1, 2025

Key West, Florida

www.justafewfriendskeywest.com

Celebrate the music, stories, and sunshine-soaked spirit of Key West during Just a Few Friends, a four-day island-style festival held every Labor Day Weekend. Inspired by the lifestyle and legacy of a certain beloved tropical troubadour, this event invites fans, friends, locals, and curious wanderers to experience the place that helped shape the soundtrack of endless summers.

Set in iconic locations throughout Old Town, this multi-day celebration includes two Milagro Margarita Bar Strolls, a Cheeseburger Beach Battle and Tribute Concert at the Southernmost Beach Resort, a lively Second Line Memorial Procession, and the high-energy Party in the Park-a free concert at Truman Waterfront featuring nationally recognized artists and regional favorites.

Live entertainment includes:

Will Kimbrough - award-winning songwriter and co-writer of Buffett's "Bubbles Up"

The Nautical Wheelers featuring Jockey Jord and Roger Bartlett - original Coral Reefer guitarist

Nadirah Shakoor - longtime Coral Reefer vocalist

Howard Livingston and the Mile Marker 24 Band - Florida Keys legends

Plus late-night performances by Cayman Smith-Martin and more

Other festival events include author talks, pool parties, sailing excursions, the Coconut Telegraph Trolley Tour, family-friendly experiences, a mustache contest, and exclusive event badge perks. Official Event Badges grant access to featured concerts, exclusive discounts, and a locals-only QR code filled with sponsor-only offers.

Festival badges and select tickets are available now through www.justafewfriendskeywest.com. Last year, most events sold out in advance, and attendance exceeded expectations, with more than 10,000 fans gathering to celebrate music, memories, and friendship-Key West style.

Whether you're local, a longtime fan, or discovering the music for the first time, you're invited to raise a glass, kick off your flip-flops, and spend the weekend with just a few friends in paradise.

Disclaimer: All events are not affiliated with or endorsed by Jimmy Buffett's Estate or Margaritaville Enterprises.

URLs:

Facebook: https://go.evvnt.com/3202838-2?pid=91 

Instagram: https://go.evvnt.com/3202838-3?pid=91 

Category: Festivals | Festival

Artists / Speakers: Howard Livingston and the Mile Marker 22 Band, Will Kimbrough, Nadirah Shakoor, Jocky Jord, Cayman Smith-Martin, Gypsies In The Palace Buffett Tribute Band, Margaritas in Paradise, Jimmy Buffett tribute band