THROUGH THE LENS: Cayamo and Outlaw Country Cruises Provided Roots Music Fans Memorable Experiences on the High Seas

During the past 24 years promoter and organizer Sixthman has presented over 150 themed festivals on the high seas. Those festivals, which push off from its Miami, Florida home port, now number 28 and permit guests (over 300,000 so far) to be captive audiences with their favorite artists, athletes, actors, comedians, and more. Or, perhaps it’s a more apt description to say that the artists and others are the captive ones, since once on board you’re on the ship to stay. There’s no shuttling off to the next town.

Two of these festivals, Cayamo and Outlaw Country Cruise, are of note to ND readers and Lens column fans since both present stellar line-ups of roots musicians, mixing legends such as Emmylou Harris, John Hiatt, Jeff Tweedy, and Lucinda Williams with up and comers like Devon Gilfillian, Rainbow Girls, Roberta Lea, and Will Hoge.

This year Cayamo, its 17th, set sail on February 28, 2025 and returned on March 7 with stops in St. Croix, US Virgin Islands, and St. John’s, Antigua. Boom Baker, Larry John Fowler, Brenda Rosser, Alan Perry, and Mike Hammer were there to capture the action, with Boom and Brenda sharing some highlights. And with over 113 sets, plus songwriting sessions, interviews, and other activities there was a lot of action.

The 9th edition of the Outlaw Country Cruise was held the previous week, February 22-27, it visited ports in Nassau, Bahamas, and St. Thomas, ND photographer Jean Van Devanter White shared her photos with us.

With six photographers covering a couple hundred sets, there are more photos in the gallery below than usual. A true feast, one not available anywhere else.

Cayamo 2025, by Boom Baker

Contemplating Cayamo every year is like Christmas morning. I can hardly wait to get to the port to greet and catch up with old friends. This year, there were 1,852 passengers, 378 making their maiden voyage, and the 17-timers club who have been on all Cayamo Cruises was down to 35. There was also a wedding of two long-time Cayamo veterans, with Steve Poltz officiating. It was only fitting as Poltz himself was married on board during the 2020 outing.

One of the best collaborations was “Tweedy Creek” where Jeff Tweedy teamed up with Nickel Creek to perform some of his songs. Tweedy said it was a dream come true to play with the trio.

Bluegrass Situation’s Nightcap set was hosted by Fruition and included guest appearances by Sara and Sean Watkins, Daniel Rodriguez, Devon Gilfillian, John Craigie, Rainbow Girls, Roberta Lea, Simeon Hammond Dallas, and Will Hoge. Phew! The highlight was a guitar shredding between Devon Gilfillian and Fruition guitarist, Jay Cobb Anderson. It was epic.  

The “Echoes of Her” set had Ani DiFranco hosting Emmylou Harris, Grace Potter, and Mary Gauthier, with Jaimee Harris providing guitar accompaniment.

Absolutely the most fun and most hilarious songwriter in the round was Susan Werner and Friends’ “Songs Of No Redeeming Value” set with Gabe Lee, Jaimee Harris, and Robby Hecht. The amusing performances resulted in near uncontrollable laughter. The climax was when Werner and Lee held up a beach towel to hide their view from the audience while they attempted to disrobe only to reveal a topless Lee and Werner’s blouse open in the front when they dropped the towel.

Cayamo 2025, Brenda Rosser 

Cayamo is always more than a music cruise — it’s a celebration of artistry, connection, and the enduring power of song. What better way to kick things off than to have an unannounced, un-billed act perform the first set of the voyage. The anticipation was building as it’s always someone special. And it was: I’m With Her, playing together for the first time in five years.  I also loved Nickel Creek’s mesmerizing show, and Fruition’s first appearance on board, as well as newcomer Whitney Mongé.

Gabe Lee and his backing band King Margo put on a fun set kick off on Saturday. Lee was voted a “Soundcheck” artist on the boat last year; he deftly handled the leap from Soundcheck to the ship’s largest stage. Lee also hosted “Cayamo After Dark,” a late night session. It was an all-piano show with Susan Werner and John Fullbright, which quickly became mostly covers featuring songs by The Beatles, John Prine, and even Supertramp, among others, with sing-a-longs being encouraged. The highlight was when all three sharing a single keyboard doing Elton John’s “Crocodile Rock.”

Jaimee Harris’ set, with Fullbright’s band backing, was masterful. Her powerful voice and skillful guitar playing created a sound that is both timeless and contemporary. She brought me to tears with “Worthy,” and I appreciated her inclusion of Nanci Griffith’s “Ford Econoline.”

John Driskell Hopkins opened his Pool Deck set with a video about his diagnosis of ALS, and the foundation he has formed.  It was a show of emotionally moving songs that also highlighted his talented band members, Leah Calvert and Mike Rizzi.

Click on any photo to view the gallery as a full-size slideshow.