Kenny Chesney Heads To Key West For 'Carry On' Video

Official Announcement | Published: May 14, 2026 4:48 PM EDT

(EBM) Beyond the obvious, there's the essence of old Key West - a place where poets, pirates, painters and passionistas live and dream. For Kenny Chesney, infused with the magic of the writers' haven by no less than Jimmy Buffett, it's the characters, old bars, dusty streets and often unseen places that have drawn him to the storied town for years.

And after locking down the entire country radio panel in its very first week, "Carry On," a sweeping single that invokes Schooner Wharf, an open-air bar on William Street's historic Harbor Walk, needed an equally historic video. So, the songwriter/superstar from East Tennessee decided to show people seeking freedom, joy or just an escape what makes classic Key West so magnetic. Working alongside longtime collaborator Shaun Silva, the pair created a set of performance "Polaroids" intercut with those side streets and disappearing moments.

"Key West isn't about who you are," Chesney explains, "but what's in your soul. It's the great equalizer, with wisdom to be found just about anywhere if you listen. I knew I wanted this video to show people that heart - beyond what tourists see - and give them a sense of what this song's really reaching into in terms of how to live."

Whether on his bicycle, making his way through local neighborhoods, a boat out on the ocean or holding down the bar at Schooner Wharf, Chesney delivers a to-the-camera performance that creates a link to every dreamer playing for tips in a city where Ernest Hemingway, Shel Silverstein, Thomas McGuane, Jerry Jeff Walker, Tennessee Williams and, yes, Jimmy Buffett drew inspiration. As much an homage to the young man he once was as a reminder to not miss the lessons that are scattered in your daily journey, "Carry On" was shot to double down on the shoot your shot, savor the moment approach to life that's defined Chesney and No Shoes Nation.

"It's a different kind of freedom," Chesney offers. "People here aren't running after anything, but letting go of all that - and hanging onto what makes them happy. That's the deal, really. It's what I wanted this video to represent, and what I think reflects how this song hits me."

Three minutes of feel good groovage that offers some bartender wisdom over moments of reggae undertow, bluegrass harmonies and a summer anthem chorus, "Carry On" became only the third single in Mediabase history to close out the panel in its first week. It celebrates noted artist/sailor and musician David Wegman, who first captured people's imaginations in Heart Life Music, Chesney's No. 1 New York Times Hardcover Nonfiction and Combined Print & E-Book Nonfiction debut.

"If you want to understand making the most of every day, of filling your time with creativity and laughter and adventure, David Wegman is all of that, and more," Chesney enthuses of his special guest star. "When we started filming, I wanted him to be part of this, so people could see what 'Carry On' draws from. We had the best day shooting at his place, where you never know if you'll find painters, musicians on tour or just friends from somewhere around the world... But that's what makes it so awesome. Open your arms and just welcome what life brings you."

With 158 stations out of 158 stations buying in, "Carry On" embodies everything great about who and what Kenny Chesney is. After all, if it feels good, do it... feels like a full-tilt summer refrain.