The Outlaw Country Cruise Keeps Swinging With Asleep at the Wheel

by Kevin Wierzbicki

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Who better to keep the Outlaw Country Cruise swinging than the kings of western swing themselves, Asleep at the Wheel? Music cruise specialists Sixthman put together a stellar lineup for the 2026 sailing of the Outlaw Country Cruise which happened to be the 10th anniversary of the beloved festival at sea. Taking place March 20-25 aboard the Norwegian Cruise Line ship Pearl, the Outlaw Country Cruise boasted performances by the like of the Nitty Gritty Dirt Band, Steve Earle, Margo Price, Jim Lauderdale, Southern Culture on the Skids, Jesse Dayton, Swamp Dogg and dozens of others.

One of the most highly-anticipated acts this year was Asleep at the Wheel, the long-running western swing band led by the deep-voiced Ray Benson. On March 21, the first of two "at sea" days for the Outlaw Country Cruise, Benson led his band through an impressive set that included favorites like "Miles and Miles of Texas," "Milk Cow Blues" and a cover of the Bobby Troup chestnut "(Get Your Kicks On) Route 66."

In a nod to their icons Bob Wills and His Texas Playboys, the all-time great western swing band, Asleep at the Wheel played the Wills tune "Faded Love." And speaking of Wills, the guys also reeled off their version of Waylon Jennings' "Bob Wills is Still the King." The show was one of the musically sweetest of the cruise, powered by fiddle, steel guitar and Benson's "voice of God" vocals.

Some of the other acts performing on the first sea day were the trio Unbepamen who are Matt Stevens, Pete Murcott and Billy Hamill. The three performed on acoustic guitars, mostly taking turns playing their self-penned songs. Roland Dixon also performed on acoustic guitar, by himself.

But on the big Pool Deck Stage, Los Angeles band NOCONA rocked the crowd with their raucous Texas-informed outlaw country rock. At sea days were also a good time for cruisers to explore some of the other things the Outlaw Country Cruise had to offer, like the opportunity to purchase a tattoo from Liberty Tattoo where tat artist Jason and several others applied ink to interested outlaws.

A must-do was a visit to the Outlaw Country Cruise merch store where just about every act had goodies for sale; t-shirts, vinyl, CDs and other assorted items were sailing out the door! Also in the merch store was where cruisers could buy raffle tickets for a chance to win Outlaw Country Cruise swag like autographed albums from the Beat Farmers and an autographed bass drum head with the colorful Outlaw Country Cruise logo. Proceeds from the raffle were slated to be donated to charity. Also in the merch store fans could see and purchase clothing items from Elizabeth Cook's Women for Sheriff clothing fashion line which included bandannas and other pieces of clothing. Later in the cruise there would be a fashion show featuring the line.

On the third day of the Outlaw Country Cruise the Pearl would arrive in Harvest Caye in Belize; our next article will detail some of the fun that happened there. For information on the 2027 sailing of the Outlaw Country Cruise go here.

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