If you are planning to book an overseas trip in the sun next year and love country music, why not choose a holiday at sea filled with sunshine and country music? Picture the scene: a seven-day, once-in-a-lifetime cruise visiting the western Caribbean with like-minded people on board, all sharing the same love for country music as you. Add live country music to the mix with artists you already know and love and you’ve got it made! It’s a trip you can even take on your own, as you’ll undoubtedly make friends in no time. You won’t just be soaking up the sun and live music as the cruise has so much more to offer such as activities, the best kind of food and drink and so much more!
Flying Dutchmen Travel is proud to announce its seventh Country Cruising adventure, setting sail in Spring 2027, for seven nights. Departing from Tampa, Florida, the festival-at-sea returns to the Celebrity Summit, traveling April 11-18, 2027.
The voyage is scheduled to visit Western Caribbean ports: Cozumel, Belize, and CostaMaya, with a star-studded lineup including some of Country music’s finest singer/songwriters. For more information and to book cabins, visit countrycruising.com.
The first of numerous lineup announcements include Randy Travis and his More Life Tour, Craig Morgan, Paul Overstreet, and James Dupré as well as fan-favorites from the last sailing, Whey Jennings, Dirty Grass Soul, and Chad Bushnell.
One of the most respected multi-genre artists of all time, Randy Travis will bring his renowned More Life Tour to the ship featuring lead vocalist James Dupré. Dupré will perform classic hits from the legend’s iconic career, with his original touring band to celebrate Travis’ everlasting legacy. The seven-time GRAMMY award winner will be onstage with his wife Mary, interacting with fans as he is unable to sing due to aphasia from his 2013 stroke. Last year, the tour played over 50 venues to 60,000+ fans across the country. Due to overwhelming demand, the tour returns this spring for a limited run. In addition to the More Life Tour shows, special programming will pay tribute to the Country Music Hall of Fame member throughout the week.
Craig Morgan is a singer, actor, author and soldier who has amassed more than 2.5 billion career streams and over 25 songs on the Billboard charts. A 2008 inductee of the Grand Ole Opry, Morgan’s music has formed the soundtrack to our lives for two decades, including hits “Redneck Yacht Club,” “Almost Home,” “Soldier,” and “That’s What I Love About Sunday.” Prior to becoming a country music star and TV sensation, Craig spent seventeen years serving our country in the Army and Army Reserve and in 2023 enlisted again in the Army Reserve, continuing his military career as a Chief Warrant Officer 2. He remains committed to supporting active duty and veteran members of our military through work with Operation Finally Home, the USO and more.
Fittingly on theme, renowned Country singer/songwriter Paul Overstreet, will head up one of Country Cruising’s biggest fan favorites, the heralded Songwriters Rounds. Featuring fellow artists on the ship, alongside Overstreet’s impeccable track record of hit songs like “When You Say Nothing At All,” “Forever and Ever, Amen,” and “Deeper Than The Holler,” the two-time GRAMMY award winner brings his influence and expertise to the party. Overstreet has collected several accolades during his 40+ year career including multiple ACM, CMA, and Dove Awards. The NSAI Songwriter’s Hall of Famer released his latest single, “Doin’ It to Country Songs” last month to Texas Radio.
James Dupré will also be performing his own sets onboard including favorites from recent solo projects, It’s All Happening and Perfect Time. Dupré was a season nine contestant on NBC’s The Voice, gracing the stage as a representative of team Adam Levine. The Rolling Stone “Country Artist You Need To Know” continues to release music regularly while touring the nation with Randy Travis’ More Life Tour as the recurrent lead vocalist.
Country musician Whey Jennings, Bluegrass/southern rock band Dirty Grass Soul, and Americana vocalist Chad Bushnell are confirmed to return to Country Cruising following their notable 2025 onboard performances.
Last year’s cruise sailed from Fort Lauderdale, Florida, to Nassau, Bahamas, providing a first-class sailing experience for guests. Featuring onboard activities including rum tastings, poker tournaments, live podcasts, and line dancing, Country Cruising brought the party! Voyagers were also invited to take part in multiple shore excursions including food tours, dolphin watches, ecological adventures, and snorkeling in the clear, blue water. Emceed by award-winning radio broadcaster Storme Warren, the ship hosted 2,000 country music fans of all ages, and past cruisers are still raving about their trip.
“This was my first cruise and it was amazing! We are definitely coming back in 2027!”
(- Kimmie M., Country Cruising Guest)
“We have already put our deposit down for 2027. We had an amazing week, so much talent on this amazing outing!”
( – JP L., Country Cruising Guest)
Since its inception, Country Cruising has long been known for its unique itineraries and one-of-a-kind live shows. Past performers include Blake Shelton, Chris Young, Kelsea Ballerini, Trace Adkins, LOCASH, Clay Walker, Taylor Austin Dye, and many more.
About Randy Travis
With lifetime sales exceeding 25 million, Randy Travis is one of the most successful multi-genre artists of all time and a 2016 inductee into the Country Music Hall of Fame. He has been a member of the Grand Ole Opry since 1986. His accolades include seven GRAMMY Awards, 11 Academy of Country Music Awards, 10 American Music Awards, two People’s Choice Awards, seven Music City News Awards, eight Dove Awards from the Gospel Music Association and five Country Music Association Awards. Three of his performances earned CMA Song of the Year honors: “On the Other Hand” (1986), “Forever and Ever, Amen” (1987), and “Three Wooden Crosses” (2002). To date, he has 23 No. 1 singles, 31 Top 10 hits, and more than 40 appearances in feature films and television shows. His discography includes four Gold albums, four Platinum albums, one Double Platinum album, one Triple Platinum album, and one Quintuple Platinum album. In 1992, Travis was recognized by the USO for his support and dedication to US Troops, including five USO tours, and was named the recipient of the Bob Hope Entertainment Award. In 2004, Travis was honored with a star on the Hollywood Walk of Fame and is celebrated on Nashville’s Music City Walk of Fame. Since his near-fatal stroke in 2013, Travis, with the support of his wife Mary and rigorous physical therapy, has made significant strides in his recovery, including improvements in speaking, walking and singing. In 2019, he released his critically acclaimed memoir Forever and Ever, Amen, co-authored with Ken Abraham. In 2021, CMT named Travis the CMT Artist of a Lifetime. In 2022, he released his award-winning documentary More Life garnering six Telly Awards. In May 2024, With the assistance of AI, Travis and Warner Music Nashville released “Where That Came From,” marking his first new recording in over a decade, showcasing his signature vocals. The single debuted at No. 45 on Billboard’s Country Airplay chart, receiving an enthusiastic reception from both fans and country radio. For more information, visit RandyTravis.com.
About Craig Morgan
Singer, author, actor, and soldier Craig Morgan has made a name for himself as a country music hitmaker who has amassed more than 2.5 billion career streams and charted over 25 songs on Billboard. With signature hits including “Redneck Yacht Club,” “Almost Home,” “International Harvester,” “Soldier,” “That’s What I Love About Sunday,” and his faith-filled tribute, “The Father, My Son, and the Holy Ghost,” the multi-faceted entertainer’s music has formed the soundtrack to our lives for over two decades. His new music, American Soundtrack (BBR Music Group/BMG Nashville), is no exception, with each of the EP’s six songs infused with Craig’s faith and patriotism. Craig received one of country music’s highest honors when he was inducted as a member of the Grand Ole Opry in 2008. Prior to becoming a country music star and TV sensation, Craig spent 17 years serving our country in the Army and Army Reserve and in 2023 enlisted again in the Army Reserve, continuing his military career as a Chief Warrant Officer 2. He remains an avid supporter of America’s military personnel and has made nearly two dozen overseas trips to perform for our troops. Craig is a member of the U.S. Field Artillery Hall of Fame and recipient of the USO Merit Award. In 2018, he was awarded the Army’s Outstanding Civilian Service Medal, one of the highest awards the Department of the Army can bestow upon a civilian, in recognition of his significant dedication to our military men and women around the world. He remains committed to supporting active duty and veteran members of our military through work with Operation Finally Home, the USO and more. His emotional and inspiring memoir – God, Family, Country – is available now. In the book, Craig details all aspects from his inspiring life, revealing never-before-heard stories including the impetus behind his recent enlistment in the Army Reserve, how he worked alongside the CIA as a soldier in Panama, fought sex traffickers as an undercover agent in Thailand, forged his own path to country music stardom, and lives his life by the deepest values: God, family, country. Learn more at craigmorgan.com and engage with Craig on socials HERE.
About James Dupré
James Dupré was born and raised in Bayou Chicot, Louisiana. He was named one of Rolling Stone Magazine’s “Country Artists You Need to Know” and has spent years sharing his smooth baritone voice with his fans across social media and at venues and festivals across the United States, Canada, and Europe. The one-time aspiring meteorologist turned paramedic became a YouTube sensation in 2007 which ultimately led to an invitation to perform on The Ellen Degeneres Show. Shortly after, he released his debut album It’s All Happening in 2010, which charted on Billboard. After signing a record deal with Warner Music Nashville in 2011, Dupré began performing and touring full-time. In 2015, Dupré appeared on NBC’s The Voice (Season Nine) with a four chair turn, landing him a spot on Adam Levine’s team. Following his departure from The Voice, James released his sophomore album Stoned to Death, yielding two singles charting on the Billboard Indicator chart: “Hurt Good” and the title track. The father of five made his acting debut in the film The Price playing the son of a country singer portrayed by Randy Travis. In 2019, James was handpicked by Randy and his wife, Mary, as the special guest vocalist for the “More Life” Tour. Along with Randy’s original band, James performs all of the Country Music Hall of Famer’s biggest hits. James released his third studio album, Home and Away, in 2020 with three singles: the title track, “Another Love Song,” and “Painfully Pretty.” In September 2023, he made his Grand Ole Opry debut in Nashville, Tenn.. In May 2024, James was featured on CBS Sunday Morning as being the first ever “vocal bed” on a commercially released song. The single, “Where That Came From,” was the first new music released by Randy Travis in over a decade, and was produced with the help of Artificial Intelligence to reimagine Randy’s legendary vocals on new music. For more information, visit JamesDupre.com.
About Flying Dutchmen Travel
At Flying Dutchmen Travel (FDT), we specialize in crafting unforgettable travel experiences designed around you. With over 50 years of experience, we’ve helped more than 150,000 travelers create memories that last a lifetime. Whether you dream of a music-themed cruise, a family getaway, or an adventurous river cruise, we ensure that every journey is perfectly tailored to your desires. Since our founding in 1974, we’ve become known for our personalized service and commitment to excellence. In 2010, we broke new ground by booking our first music charter with Royal Caribbean Cruise Line (RCL). This move transformed the industry and helped us become RCL’s number-one charter client in just ten years. Our cruises have featured artists like Blake Shelton, Melissa Etheridge, Kenny Loggins, and Dave Koz, allowing travelers to connect with their favorite performers on the open sea. As the only woman-owned agency in the music charter space, we bring a fresh perspective to every planned trip. With a deep understanding of global travel, we’re here to meet your personal and group travel needs— whether you’re looking for adventure, relaxation, or a unique event experience. To explore FDT’s new offerings or to start planning your next adventure, visit flyingdutchmentravel.com.
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