Everything You Need to Know About the Key West Songwriters Festival

It wouldn’t be spring in Key West without the annual Key West Songwriters Festival. This iconic festival - and largest of its kind in the world - honors nearly 200 veteran and up-and-coming artist/songwriters who write hits for country, folk, pop, blues, and rock’s hottest music billboard acts. For five days and nights, May 3 - 7, 2023, artists take over Key West venues, perform their original songs, and tell the stories behind them.

The beauty of the KWSF is that it provides the chance to hear the songs you know and love in their most basic form. It’s also a great opportunity for songwriters to connect, network, and make a name for themselves. In fact, the festival has been credited with helping to launch artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris to superstardom.

Here’s everything you need to know about the annual Key West Songwriters Festival, including dates, ticketing info, and the most anticipated events of 2023. Read on.

Key West Songwriters Festival 2023 Dates

This year, the festival will run from Wed. May 3 through Sun. May 7, 2023.

Key West Songwriters Festival 2023 Location

KWSF is one of the liveliest times of the year in Key West and an excellent way to visit select venues all over the island. Musical acts will be performing at Key West mainstays like the Key West Theater, Blue Heaven, Irish Kevin’s, Schooner Wharf Bar, Green Parrot, Sloppy Joe’s, Conch Republic Seafood Co., and even 24 North Hotel’s very own Sunset Green Event Lawn.

[See Raul Malo and Kostas at 7:30 p.m., followed by Robert Randolph, Timmy Sims, Jeffrey Steele, and the Dylan Altman Blues Band at 9 p.m. on May 4 at the Sunset Green Event Lawn. Get your tickets to this Key West Songwriters Festival event before it sells out!]

Key West Songwriters Festival 2023 Lineup and Schedule

Headlining this year’s 27th annual festival is singer/rapper/songwriting sensation Jelly Roll, alongside acts Elle King, Mitchell Tenpenny, Rivers Rutherford, Raul Malo, The Love Junkies, Robert Randolph, Michael Ray, Marti Frederiksen, and Jeffrey Steele. We’ve only included where to see these hot ticket shows below, but check out the full Key West Songwriters Festival schedule here.

-Robert Randolph: May 3, 7 p.m. at Sunset Pier Kick Off Party at Ocean Key Resort. Visit KWSF website for ticket info.; May 4, 9 p.m. at Sunset Green Event Lawn at 24 North Hotel. Tickets.

-Marti Frederiksen: May 3, 9 p.m., Key West Theater. Tickets.

-Jeffrey Steele: May 3, 10 p.m. at Key West Theater. Tickets.; May 4, 9 p.m.; Sunset Green Event Lawn at 24 North Hotel. Tickets.

-Mitchell Tenpenny: May 4, 4 p.m. at Key West Theater. Tickets.

-Michael Ray: May 4, 5:30 p.m. at Key West Theater. Tickets.; May 6, 7 p.m. at Songwriters Main Stage at the 200 Block of Duval Street beginning. Free.

-Raul Malo: May 4, 7:30 p.m. ay Sunset Green Event Lawn at 24 North Hotel. Tickets. May 6, 9:30 p.m. at Key West Theater. Tickets.

-Elle King: May 4, 8 p.m. at Key West Theater. Tickets.

-The Love Junkies: May 4, 9:30 p.m. at Key West Theater. Tickets.; May 5, 9:30 p.m. at San Carlos Institute. Tickets.

-Jelly Roll: May 5, 8 p.m. at Key West Amphitheater. Tickets.

-Rivers Rutherford: May 5, 8 p.m. at San Carlos Institute. Tickets.; May 6, 9:30 p.m. at Key West Theater. Tickets.

Best Events of Key West Songwriters Festival 2023

The five nights of the festival are stacked with stellar performances, but we think these events offer something extra special:

The Key West Theater will have more than one Bloody Mary Bash featuring music and a Bloody Mary menu. The May 4 show will be with Danny Myrick and Bob DiPiero, followed by Earl Bud Lee & Friends on May 5. Shows begin at 10:30 a.m.

The Fury Catamaran is getting in on the festival action as well by hosting a Live Music Sunset Sail on May 4 and 6 at 6 p.m. The sails feature live musical performances by KWSF artists, plus appetizers, margaritas, and a full liquor bar. Performers on the bill include Bridgette Tatum (who co-wrote Jason Aldean’s mega hit “She’s Country”), Andi-Zack-Johnson (who has written for Brothers Osborne, Danielle Peck, Vince Gill, and Josh Thompson), Ken Johnson (who has written for artists like Harry Connick Jr. and Uncle Kracker), Lewis Brice (named one of Rolling Stone Country’s “New Country Artists You Need to Know”), Emma Zinck, Seth Michael, and Key West local Nick Norman.

For a block party bash with the Key West community, check out the Songwriters Main Stage at the 200 Block of Duval Street beginning at 7 p.m. on Saturday, May 6, hosted by radio broadcaster and "Dick Clark of Nashville," Storme Warren. The free show will star Jordan James, Meg McRee, Ben Chapman, and Michael Ray.

Key West Songwriters Festival 2023 Tickets

Many of the festival venues are free to enter and shows typically begin early in the afternoon before playing well into the night. Places like the Key West Theater, San Carlos Institute, Sunset Green Event Lawn, and Coffee Butler Amphitheater will host the bigger names of the festival, so grab your Key West Songwriters Festival tickets to these events in advance. For unprecedented access to all the shows, check out the Platinum ticket option.

The Key West Songwriters Festival is a quintessential slice of Americana that meshes perfectly with the laid-back vibe of Key West. So get down to the KWSF, happening May 3 - 7, 2023, and pack your guitar, we’ve got just the space for it and plenty more for you at 24 North Hotel. Book direct to save up to 25% and see which of our special offers works for you.

For more live tunes, stop by Republica Bar & Lounge inside 24 North Hotel. The Cuban-inspired craft cocktail lounge features an exciting mixology menu, complemented by charcuterie boards and live music seven nights a week.