The largest festival of its kind, the Key West Songwriters Festival returns May 3 - 7, 2023 to celebrate the most successful, chart-topping songwriters in country music. KWSF is their chance to take center stage, whether it be performing for thousands on the biggest stages on the island, or in more intimate settings where they are apt to engage more authentically with their audience. That said, here are the artists to keep on your radar at the Key West Songwriters Festival 2023:

Bridgette Tatum

Live on the Fury Catamaran on Thurs. May 4, 2023 @ 6 p.m. Tickets.

You may know Bridgette from the most-played song of 2009 - Jason Aldean’s hit “She’s Country” - which she co-wrote. Tatum’s repertoire is as long as it is robust with star power, writing hit songs for artists like Gretchen Wilson, Randy Houser, and Ashley Cooke. And if that’s not enough, the artist/songwriter/producer continues to build her empire with a mentoring service for aspiring songwriters. Catch Bridgette aboard the Fury Catamaran for a special sunset sail, which includes performances by more KWSF artists, plus appetizers, margaritas, and a full liquor bar.

Jeffrey Steele

Live @ Sunset Green Event Lawn on Thurs. May 4, 2023 @ 7:30 p.m. Tickets.

Jeffrey Steele is both singer and songwriter. With credits on tracks by Tim McGraw, Faith Hill, LeAnne Rimes, Rascal Flatts, Billy Ray Cyrus, and others, Steele has charted many of his own material throughout the decades. See Jeffrey Steele live at the Sunset Green Event Lawn at The Gates Hotel, along with a stacked lineup including Raul Malo and Kostas, Robert Randolph, Timmy Sims, and the Dylan Altman Blues Band (see more on the Dylan Altman Blues Band next).

Dylan Altman Blues Band

Live @ Sunset Green Event Lawn on Thurs. May 4, 2023 @ 7:30 p.m. Tickets.

Dylan Altman has become quite the popular fixture on the country music circuit, writing songs for Tim McGraw, Jake Owen, Trace Adkins, and Jason Aldean. You’ll find him performing live every day of the festival (Wed. May 3 @ Sunset Pier Kick Off Party @ 6:30 p.m.; Fri. May 5 @ Green Parrot @ 5:30 p.m. and 10 p.m.; Sat. May 6 @ Curry Mansion @ 5 p.m.; and Sun. May 7 @ Key West Theater @ 9 p.m.), but we’ll be at his May 4 performance at the Sunset Green Event Lawn - it’s our backyard!

[Looking for more experiences aboard the Fury? The Gates Hotel has partnered with the catamaran to offer an exclusive Fury Excursion Package which includes up to 25% off your nightly rate, plus you get to choose one of their unforgettable Key West watersport experiences like a sunset sail or snorkeling around North America's only living coral reef.]

Elle King

Live @ Key West Theater on Thurs. May 4, 2023 @ 8 p.m. Tickets.

You may recognize Elle King from movies alongside her famous father Rob Schneider, but King is first and foremost, a four-time Grammy-nominated singer/songwriter whose voice and music speaks for itself. Sing along to her top 10 single “Ex’s and Oh’s” at the Key West Theater with The Love Junkies, Ella Langley, and Madeline Edwards.

Jelly Roll

Live @ Key West Amphitheater on Fri. May 5, 2023 @ 8 p.m. Tickets.

Best known for his collaborations with Lil Wyte, Struggle Jennings, and Tech N9ne, Jelly Roll is having quite the breakout year. The rapper/singer/songwriter just took home three CMT Music Awards for ‘Male Video of the Year’, ‘Male Breakthrough Video of the Year’, and ‘Digital-First Performance of the Year’, all for his hit "Son of a Sinner". Jelly Roll headlines KWSF, but you only have one opportunity to see the Tennessee-born songwriting powerhouse - and that’s at the Key West Amphitheater the Friday of the fest.

Michael Ray

Live on Duval Street on Sat. May 6, 2023 @ 7 p.m. Free.

Florida-born Michael Ray got his big break after winning The CW’s The Next: Fame is at Your Doorstep, and has since gone on to top the charts with his original music. The best thing about his KWSF performance: it’s absolutely free. Radio broadcaster and “Dick Clark of Nashville” Storme Warren hosts the free outdoor concert at the KWSF Main Stage at the 200 block of Duval Street. The show also features Jordan James, Meg McRee, and Ben Chapman.

For the complete line-up of artists, visit the Key West Songwriters Festival 2023 schedule.

Booking a trip to Key West Songwriters Festival 2023? The Gates Hotel Key West is recognized by Condé Nast as one of the best hotels in Florida. Located in New Town, our regular shuttle service to Old Town makes your trip as laid-back and relaxed as the tunes you’ll be enjoying during the festival. Enjoy a day by the pool with bites from our food truck or a drink from our onsite bar and cigar lounge. See our special offers, which include exclusive rates just for Florida residents.