The Outlaw Country Cruise: Summer Dean Gets the Party Started

by Kevin Wierzbicki

It was only a coincidence that the first day of this year's sailing of the Outlaw Country Cruise fell on the first day of spring. But what better way to tell winter to get lost than five days of fun in the sun? The Outlaw Country Cruise celebrated a 10th anniversary in 2026 and took place March 20-25 aboard the Norwegian Cruise Line ship Pearl as she cruised from Miami to the exotic ports of Harvest Caye in Belize and Roatan in Honduras. The music cruise specialists at Sixthman put together a fantastic lineup for the floating festival that included Lucinda Williams, Nitty Gritty Dirt Band, Steve Earle, Asleep at the Wheel, Jim Lauderdale and many other exciting performers. And getting the honor of being the first act to perform this year was Texas honky-tonker Summer Dean.

Summer Dean

A sassy performer to be sure, Dean wore an ever-present grin as she sang and shimmied her way through her show on the Pearl's Atrium stage, a relatively intimate venue. Backed by a crack band that included vaunted pedal steel player Geoff Queen, the vibe in the venue was pure honky-tonk as Dean reeled off fun cuts like "Somebody's Knockin'," the amusing "Yes Ma'am, He Found Me in a Honky Tonk" and a song she sang at her Grand Ole Opry debut last year, "She Ain't Me," which she dedicated to her "future mother-in-law." Summer also noted that the song was first released by Leona Williams who at one time was married to the great Merle Haggard. Another song that Summer sang was her own composition "She's in His Arms But I'm in the Palm of His Hand."

Shortly after Summer Dean's opening show, the Outlaw Country Cruise officially got underway with the traditional "family photo" where everyone gathered at the pool deck to raise a complimentary whiskey sour shot and toast the good times ahead. Then Jesse Dayton played a rowdy set for the sail-away show as the Pearl moved out of Miami bound for Belize. Among the songs that Dayton performed was the Waylon Jennings favorite "Don't You Think This Outlaw Bit's Done Got Out of Hand" and he also told a funny story about Waylon. One time when Dayton was on tour with Jennings, Waylon came to him and said "Well Hoss, they want me to do the Lola Falana tour." Puzzled by the comment, Dayton later found out that what Waylon meant to say was "Lollapalooza." Jesse also played the stomping "The Ballad of Boyd Elder," the modern rocking country "Daddy Was a Badass" which included a long guitar solo and "I May Have to Do It (Don't Have to Like It)."

Jesse Dayton

Other highlights of the first day of the Outlaw Country Cruise included a packed show in the Atrium by Southern Culture on the Skids. The band treated the crowd to a set that included songs from throughout their career including the favorites "Nitty Gritty" and "Liquored Up and Lacquered Down."

Southern Culture on the Skids

Meanwhile Andrew Leahey, who often plays with a full band, played a solo acoustic show at the ship's medium-sized venue Magnums. At one point Leahey took requests from the audience which overwhelmingly requested that he play "Guilty Man" and he nicely obliged.

Andrew Leahey

Another great show was Swamp Dogg in the large Stardust Theater. Strong of voice and quick with a quip, many of which were littered with profanities, the nearly 84-year-old soul singer thrilled a packed house with songs like "The World Beyond," the long and rocking soul jam "If I Die Tomorrow (I've Lived Tonight" and the oft-covered country standard that was a hit for Johnny Paycheck, "(Don't Take Her) She's All I Got." Trivia buffs will know that the song was written by Swamp Dogg, under his real name Jerry Williams, Jr., along with the rock 'n' roll legend Gary U.S. Bonds. Noting his age and the fact that he stopped getting Social Security payments a long time ago, Swamp Dogg joked that he would be grateful for anyone sending him money by Zelle.

Swamp Dogg