Key West Songwriters Festival: A "Who's Who" of Hit Writers and Artists

Stories behind the songs in idyllic locale 

What could be better than a week of songwriter rounds?  How about a week of songwriter rounds and surprise artist appearances under palm trees ruffled by tropical breezes with the deep blue Atlantic to the east and the shallow flats of the Gulf of Mexico to the west?

That’s the way it was at the 27^th Annual Key West Songwriters Festival, May 3-7, 2023. Even if you weren’t aware of the Festival, the dozens of guitar cases being lifted down from the aircraft overhead bins and even more circling on the baggage claim carousels at Key West International Airport were a pretty good clue that something special was happening.

BMI was ‘the Hostess With the Mostest’ (or ‘the Hosts With the Mosts’) for the Festival alongside Rams Head Presents and The Florida Keys Tourist Development Council. The yearly tradition brings together music lovers and music fans to watch over 250 songwriters perform across the island.

Once again, the list of artists and songwriters appearing during the Festival was a “who’s who” of music talent that encompassed multiple music genres and fans could choose from more than 50 plus shows at venues across the island with over 30 free events.

As with Nashville’s Tin Pan South, the Festival’s shows were spread across many venues from the Key West Amphitheater and Salty Frog’s to the Hard Rock Café and Sloppy Joe’s and plenty more as well.  Those guitar cases were seen zipping along with their owners on golf carts or lined up stageside ahead of shows.

So many magic moments at almost every show with songwriters sharing the stories behind the well-known songs and premiering new music in this idyllic location. (Dates for the 2024 Festival are already set. See below.)

One of my favorite events of the entire Festival was the NSAI invitation-only brunch, hosted by Nashville Songwriters Association International (NSAI), The Mechanical Licensing Collective (MLC) and The Bluebird Café.

At the NSAI brunch, we got to watch and hear some incredible songwriters including Brian White, Doug Johnson, Liz Rose, Keesy Tinmer and Rebecca Lynn Howard, with the special performances hosted by Phil Barton. Perhaps best of all, I also got to hang with our NSAI music family!  

The 2023 lineup included Jelly Roll - he did not disappoint with his swirling genres from country rock to his song rapping favorites, three-time Grammy Award-nominee Elle King, one of the most talented and easy-on-the-eyes country stars Michael Ray, country newcomer Mitchell Tenpenny, renowned songwriter Rivers Rutherford, festival favorite James Slater, prolific chart-topper my friend Jeffrey Steele, former Mavericks frontman Raul Malo and the songwriting super-trio dubbed the Love Junkies (Hillary Lindsey, Lori McKenna and Liz Rose), Jack Ingram, Robert Randolph and more hit songwriters and country stars. 

Each show featured songwriter rounds, during which writers showcase their hits and share the stories behind their biggest songs. Randolph took the stage with the Dylan Altman Blues Band and James Slater performed during Wednesday night’s kick-off party at Ocean Key Resort’s Sunset Pier, followed by performances from Bob DiPiero, Luke Laird and Steele. Jelly Roll was Friday evening’s headliner and Ray rocked the streets during Saturday night’s block party. Other featured acts include Ronnie Bowman, Kostas, Ella Langley and Emily Shackelton. Saturday was a free “block party” high-energy performance by Michael Ray in the heart of Duval Street. Nothing short of amazing! See the full lineup here. 

Most of the festival’s shows featured a rotating group of performing songwriters and free admission. The whole city joined in with shows being presented at island city bars, restaurants, resort beaches and poolsides as well as event headquarters, the Rams Head Southernmost Bar & Restaurant at 804 Whitehead St.

The Key West Songwriters Festival is the largest festival of its kind in the world and is known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. In its 27th year, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.

The dates for next year’s Key West Songwriters Festival have now been announced: May 1 – May 5, 2024. It’s never too early to plan ahead for travel and lodging.  Hope to see you there! 

More about the Kew West Songwriters Festival here.