There are music festivals… and then there is the Key West Songwriters Festival.
From April 29 through May 3, 2026, Key West transforms into one giant live music venue filled with acoustic sets, surprise performances, unforgettable stories, and the songwriters behind some of the biggest hits in country music.
And the best part? Many of the performances happen in intimate island bars, waterfront venues, historic theaters, and beachside stages where you are only a few feet away from the artists.
It is personal, authentic, and very Key West.
Why This Festival Is Such a Big Deal
The Key West Songwriters Festival is the largest festival of its kind in the world and has become known as a launching pad for future stars.
Artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Randy Houser, Michael Ray, and Maren Morris all played this festival before becoming household names.
That is what makes it different.
You are not just watching concerts. You are hearing the stories behind the songs, often from artists who wrote them before the rest of the world catches on.
Daily Event Guide 2026
Here is your easy to follow breakdown of the Key West Songwriters Festival so you know where to be, when to go, and which venues you absolutely should not miss.
Tuesday April 28 – The Early Kickoff Energy
📍 Island Dogs Bar - Come as you are!
505 Front Street, Key West, FL 33040
🕘 9:00 PM
• Come As You Are kickoff party
The unofficial start to festival week. Expect locals, songwriters, and visitors all mixing together before the madness officially begins.
Wednesday April 29 – Festival Opening Day
📍 Dante’s Pool Bar & Restaurant
955 Caroline Street, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
📍 Southernmost House
1400 Duval Street, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
with Storme Warren hosting The Big 615 on TuneIn
📍 Wicker Guest House - Poolside Garden Stage
913 Duval Street, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
📍 Ocean Key Resort - Sunset Pier Kick Off Party - FREE SHOW
hosted by Storme Warren
0 Duval Street, Key West, FL 33040
🕕 6:00 PM Jeffrey Steele
🕕 7:15 PM The Brummies
📍 Island Dogs Bar
505 Front Street, Key West, FL 33040
🕖 7:00 PM – 10:00 PM
📍 Salty Frog’s Bar & Grill
407 Front Street, Key West, FL 33040
🕗 8:00 PM – 11:00 PM
📍 Key West Theater
512 Eaton Street, Key West, FL 33040
🕗 8:00 PM Taylor Phillips, Ashley Cooke, Tyler Reeve
🕤 9:30 PM James Slater, Aaron Raitiere, Thomas Edwards
📍 Rick’s / Dirty Harry’s Complex
202 Duval Street, Key West, FL 33040
🕘 9:00 PM – Midnight
📍 The Alamo - HD Radio Late Night Hang
4 Petronia Street, Key West, FL 33040
🕙 10:00 PM – 1:00 AM
Thursday April 30 – The Island Fully Turns Into a Music Festival
📍 White Tarpon
700 Front Street, Key West, FL 33040
🕚 11:00 AM – 3:00 PM
📍 Southernmost Beach Resort - Beach Bash
1319 Duval Street, Key West, FL 33040
🕛 12:00 PM – 4:00 PM
• Beach Bash
📍 Marquesa Hotel
600 Fleming Street, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
📍 La Concha - Hotel Pool
430 Duval Street, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
📍 Rams Head Southernmost - Dulce Vida Tequila Truck Stage
804 Whitehead Street, Key West, FL 33040
🕐 1:00 PM – 10:00 PM
📍 Ocean Key Resort Sunset Pier
0 Duval Street, Key West, FL 33040
🕑 2:00 PM – 4:00 PM
📍 The Capitana - Tropical Key West Vibes Show!
2401 N Roosevelt Boulevard, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
📍 Curry Mansion Inn
511 Caroline Street, Key West, FL 33040
🕓 4:00 PM – 6:00 PM
presented by Brightwild
📍 The Bluebird at Blue Heaven
729 Thomas Street, Key West, FL 33040
🕓 4:00 PM – 7:00 PM Liz Rose & Friends
📍 Blue Flamingo Resort
3820 N Roosevelt Boulevard, Key West, FL 33040
🕓 4:00 PM – 7:00 PM
📍 Key West Theater
512 Eaton Street, Key West, FL 33040
🕓 4:00 PM Ryan Beaver, Heath Warren, Jeff Middleton
🕓 5:30 PM Doug Johnson, Johnny Clawson, Jordan Dozzi, Rebecca Lynn Howard, Elisha Hoffman, Hannah McFarland
📍 Marker Resort Pool Party
200 William Street, Key West, FL 33040
🕠 5:30 PM – 7:30 PM
📍 The Key West Hotel - Bali Bar
325 Duval St, Key West, FL 33040
🕔 5:00 PM – 8:00 PM
📍 Fury Sunset Sail
325 Duval St, Key West, FL 33040
🕔 6:00 PM – 8:00 PM Stephen Barker Liles, Brian Kelley
📍 Greeen House Mothership - "Smoke Out" BBQ
532 Duval St, Key West, FL 33040
🕕 6:00 PM – 9:00 PM DJ Smoke, Mike Stack and D-Lew
📍 Lunara Live: Waterfront
Solaire at Lunara Bay - 12 Andrea Lane
🕖 7:00 PM Jenna LaMaster, Kylie Frey, Aniston Pate
🕖 8:00 PM Orlando Mendez, Tyler Reeve, Chord Overstreet
🕖 9:00 PM Ashley Cooke (Free Show)
📍 Key West Theater
🎸 Guitar Auction
🕖 8:00 PM Lee Thomas Miller, Wendell Mobley
🕖 9:30 PM Hardy, Ernest, Craig Wiseman
📍 San Carlos Institute
516 Duval Street, Key West, FL 33040
🕖 8:00 PM Chuck Mead, Guthrie Trapp, Aaron Raitiere
🕖 9:30 PM Bob DiPiero, Jeffrey Steele, James Slater, Mark Collie
📍 The Backyard at Kaya
618 Duval Street, Key West, FL 33040
🕙 10:00 PM – 1:00 AM
📍 Duval Star Karaoke @ Backyard Bar - Publisher Karaoke
Hosted by SJ McDonald
618 Duval Street, Key West, FL 33040
🕙 10:00 PM
Friday May 1 – Big Crowds and Big Names
📍 Beachside Resort & Residences Poolside
3841 N Roosevelt Boulevard, Key West, FL 33040
🕚 11:00 AM – 2:00 PM
📍 Hyatt Centric Key West Resort - Blue Mojito Bar
601 Front Street, Key West, FL 33040
🕛 12:00 PM – 3:00 PM
📍 Southernmost Resort Pineapple Pool Party
1319 Duval Street, Key West, FL 33040
🕛 12:00 PM – 4:00 PM
📍 Rams Head Southernmost - Dulce Vida Truck Stage
804 Whitehead Street, Key West, FL 33040
🕐 1:00 PM – 5:00 PM (and 5:00 PM - 10:00 PM)
Hunter Cottingham PLLC Presents: Hometown Pub Takeover
📍 Wicker Guest House Poolside
913 Duval Street, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
📍 Ocean Key Resort Sunset Pier
0 Duval Street, Key West, FL 33040
🕑 2:00 PM – 4:00 PM
Gracy Tyler & Friends presented by Dulce Vida Tequila
📍 Southernmost House
1400 Duval Street, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
Storme Warren host of the Big 615 on TUNEIN
📍 NAS Key West Sigsbee Sunset Lounge
Naval Air Station Key West
🕒 3:00 PM – 7:00 PM
*Restricted access to Military Personnel with Base Access only*
📍 Perry Hotel - Salty Oyster Dockside Bar
7001 Shrimp Road, Stock Island, FL 33040
🕓 4:00 PM – 7:00 PM
📍 Curry Mansion Inn
511 Caroline Street, Key West, FL 33040
🕓 4:00 PM – 6:00 PM
Presented by Brightwild
📍 Key West Theater
512 Eaton St, Key West, FL 33040
🕓 4:00 PM Summer Oversteet, Ava Suppelsa, Kylie Frey
🕓 5:30 PM Danny Myrick, Pauk Jenkins, Jim McCormick
📍 Sloppy Joe’s Bar
201 Duval Street, Key West, FL 33040
🕠 5:30 PM – 9:30 PM
📍 Green Parrot Sound Check
601 Whitehead Street, Key West, FL 33040
🕠 5:30 PM – 7:00 PM
📍 Key West Theater
512 Eaton St, Key West, FL 33040
🕓 8:00 PM Tommy Sims, Chuck Mead, Guthrie Trapp
🕓 9:30 PM Wendell Mobley, Chuck Cannon, Tim Nichols
📍 San Carlos Institute
516 Duval St, Key West, FL 33040
Open: TXSU Winner Gloria Anderson
🕓 8:00 PM Bruce Robison, Jack Ingram, Larry Joe Taylor
🕓 9:30 PM Robert Earl Keen, Liz Rose, Lori McKenna
Presented by Texas Heritage Songwriters Association
📍 La Te Da Cabaret
1125 Duval St, Key West, FL 33040
🕓 8:00 PM Kristen McNamara, Fancy Hagood
🕓 9:00 PM Rissi Palmer, Rebecca Lynn Howard, Elisha Hoffman
🕓 10:00 PM Shane Stevens, Tia Sillers, Danielle Blakey
📍 Curry Mansion Goes Country - FREE SHOW
511 Caroline St, Key West, FL 33040
🕠 8:00 PM Aaron Raitiere
🕠 8:35 PM Aniston Pate
🕠 9:15 PM McCoy Moore
Presented by Brightwild
📍 Irish Kevin's
211 Duval Street, Key West, FL 33040
🕠 10:00 PM – 1:00 AM
📍 Green Parrot - HD Radio Late Night Hang
601 Whitehead St, Key West, FL 33040
🕓 10:00 PM - 2:00 AM
Saturday May 2 – Peak Festival Weekend
📍 Hogs Breath Saloon
400 Front Street, Key West, FL 33040
🕥 10:30 AM – 1:30 PM
📍 Key West Theater - Bloody Mary Bash
512 Eaton Street, Key West, FL 33040
🕚 11:00 AM Robert Earl Keen & Friends
📍 Conch Republic Seafood Company
631 Greene Street, Key West, FL 33040
🕚 11:00 AM – 2:00 PM
📍 Marker Resort Pool Party
200 William Street, Key West, FL 33040
🕛 12:00 PM – 3:00 PM
📍 Winslow’s Bungalows - Key West Historic Inns
725 Truman Avenue, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
📍 Rams Head Southernmost - Dulce Vida Tequila Truck Stage
804 Whitehead St, Key West, FL 33040
🕐 1:00 PM – 10:00 PM
📍 Oceans Edge Pool Party
5950 Peninsular Avenue, Key West, FL 33040
🕐 1:00 PM – 5:00 PM
📍 Oceans Key Resort Sunset Pier
0 Duval St, Key West, FL 33040
🕐 2:00 PM – 4:00 PM
📍 Hyatt Centric Key West Report - Blue Mojito Bar
601 Front St, Key West, FL 33040
🕐 2:00 PM – 5:00 PM
📍 Rick’s / Durty Harry’s
202 Duval Street, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
📍 La Concha - Tropicado
430 Duval Street, Key West, FL 33040
🕓 4:00 PM – 7:00 PM
📍 Hellings Curry Museum
319 Duval Street, Key West, FL 33040
🕓 4:00 PM – 7:00 PM
Key West Woman's Club presents All Women's Round
📍 Curry Mansion
511 Caroline Street, Key West, FL 33040
🕓 4:00 PM – 6:00 PM
Presented by Brightwild
📍 Southernmost Beach Resort - Derby Party - South Beach Stage
1319 Duval Street, Key West, FL 33040
🕔 5:00 PM – 8:00 PM
📍 Fury Sunset Sail
631 Greene Street, Key West, FL 33040
🕕 6:00 PM – 8:00 PM
The Rum Strummers (Jacob Rice, Jeff Middleton, Justin Klump)
📍 Duval Street Stage - FREE SHOW
200 Block of Duval Street
🎸 Guitar Auction
🕕 6:15 PM DJ Smoke
🕕 7:00 PM Cody Lohden
🕕 7:30 PM Ashley Cooke
🕕 8:05 PM ERNEST
Presented by Captain Morgan & Rams Head
📍 William Weech - American Legion Post 168
Key West Cultural Center & Veterans Museaum
Suggested $5 Donation
803 Emma St, Key West, FL 33040
🕕 8:00 PM James Slater & Kristen McNamara
🕕 9:00 PM Marti Frederiksen, Steve McEwan
🕕 10:00 PM Guthrie Trapp, James Slater, Tommy Simms, DJ Smoke
📍 Key West Theater
512 Eaton Street, Key West, FL 33040
🕚 8:00 PM Tim Nichols, Trent Tomlinson, Taylor Phillips
🕚 9:45 PM Bobby Pinson, Tia Sillers, Lindsay Rimes
📍 The Backyard @ Kaya
618 Duval St, Key West, FL 33040
🕕 10:00 PM - 1:00 AM Tyler Reeve and Friends
📍 The Key West Hotel - Bali Bar
325 Duval St, Key West, FL 33040
🕕 9:00 PM - 12:00 AM
Sunday May 3 – Closing Day
📍 Williams Hall - Sunday Songs: Music & Mimosas!
In honor of Ronnie Bowman
729 Fleming Street, Key West, FL 33040
🕛 12:30 PM – 3:30 PM Butter & Grit, Elisha Hoffman, Rebecca Lynn Howard, Tommy Sims, Chuck Cannon, Danny Myrick, Megan Linville
📍 Southernmost Beach - South Beach Stage
1405 Duval Street, Key West, FL 33040
🕛 12:00 PM – 3:00 PM
📍 Sloppy Joe’s
201 Duval Street, Key West, FL 33040
🕛 12:00 PM – 4:00 PM
📍 Blue Flamingo Resort - Sunday Fun-day Pool Party
3820 N Roosevelt Boulevard, Key West, FL 33040
🕐 1:00 PM – 4:00 PM
With Dulce Vida Tequila
📍 Rams Head Southernmost - Dulca Vida Tequila Truck Stage
804 Whitehead Street, Key West, FL 33040
🕑 2:00 PM – 6:00 PM
📍 Southernmost House
1400 Duval Street, Key West, FL 33040
🕒 3:00 PM – 6:00 PM
📍 Key West Theater - ALL STAR ENCORE!
Songwriters & Stories
512 Eaton Street, Key West, FL 33040
🕗 8:00 PM - Anna Willson & Monty Powell
🕗 9:00 PM - Danny Myrick, Megan Linville, Megan Barker, Rachel LaRen
🕗 10:00 PM - Raul Jenkins, Steve McEwan, Kurtis John, Casey Levasseur
🔥 Local Tip:
Shows and schedules can shift throughout the week, especially with surprise guests and island weather. Download the official Key West Songwriters Festival app or check their website daily for updates.
What Makes the Festival Special
Unlike massive stadium festivals, the Key West Songwriters Festival feels intimate.
One moment you are listening to a Grammy winning songwriter at a waterfront sunset show. The next, you are hearing the next big artist perform in a tiny island bar with 50 people packed inside.
The entire island becomes part of the experience.
You will find performances:
- At bars on Duval Street
- On the beach
- At historic theaters
- Inside resorts and restaurants
- At hidden local venues all over the island
For 5 days, music is EVERYWHERE.
Top Artists and Songwriters to Watch in 2026
While the full lineup continues to grow, the festival is known for bringing in some of Nashville’s biggest writers along with breakout artists on the rise.
Keep an eye out for:
- Platinum selling country songwriters
- Grammy winning hit-makers
- Rising Nashville artists
- Surprise guest appearances
- Acoustic collaborations you will not see anywhere else
This festival is famous for “you never know who might show up.”
That unpredictability is part of the magic.
A Local Tip for Experiencing the Festival
Do not over schedule yourself.
One of the best parts of this festival is wandering into places you did not plan on visiting.
Some of the most memorable moments happen when you accidentally discover an artist before everyone else does.
Grab a drink, slow down, and follow the music.
Why This Festival Fits Key West So Perfectly
The Key West Songwriters Festival works because it matches the island itself.
It is creative, relaxed, authentic, and built around storytelling.
You are not just hearing songs. You are hearing where they came from, how they were written, and sometimes even the stories behind the heartbreak, parties, and life moments that inspired them.
That feels very Key West.
More Than a Festival
The festival also supports important causes including:
- The BMI Foundation
- Michelle’s Foundation
- Music education initiatives
So while everyone is having a great time, the event is also helping support the future of songwriting and young musicians.
My Final Thought
If you love live music, this is one of the best weeks of the entire year to be in Key West.
For 5 days, the island turns into a nonstop soundtrack of stories, acoustic sets, sunset concerts, and unforgettable moments.
And whether you are a country music fan or just someone who loves the energy of Key West, this festival has a way of pulling everyone in.
You Should Be Here,
🐓KWT🐓
