Country Cruising 2027 is bringing you one-of-a-kind shows and experiences that we’re incredibly proud of—events that set our cruise apart from any other.
Ready to trade the everyday for an unforgettable country music escape? Throughout the day, the decks come alive with boot-stompin’ beats at our poolside parties. As the sun dips low, mosey on over to the main theater for evening shows that’ll have you singing along like you’re front row at a stadium concert. Swing by the Sky Lounge for a little acoustic charm or cozy up in the Rendezvous Lounge for some down-home melodies that feel like a warm hug. With music echoing through the Grand Foyer and beyond, every moment is pure country bliss at sea.
Keep your eyes and ears open for surprise pop-up performances from your favorite artists—you never know where they’ll show up next! Don’t miss out!
Our roots in country music run deep, and this year on Country Cruising, we proudly honor one of the genre’s most legendary voices and most beloved figures—Randy Travis.
In this unforgettable main-stage experience, Country Cruising artists will come together to perform their own heartfelt renditions of Randy’s timeless hits as Randy shares in the
experience with the fans and fellow artists he has inspired for decades.
More than a performance, this is a collective expression of gratitude and respect—celebrating a friend, a hero, and a living legend of country music. Together, artists and guests will honor the music, the memories, and the man whose legacy continues to shape the heart of country music.
It’s a once-in-a-lifetime moment—where country music comes full circle.
Few songwriters have shaped modern country music the way Paul Overstreet has. Travis’s “Forever and Ever, Amen,” and Keith Whitley’s “When You Say Nothing At All” might
be two of the most important songs in Country music history. Overstreet co-wrote both of
them. In addition he’s had hits recorded by
George Jones, Kenny Chesney, Blake Shelton, and many more. Who can forget Overstreet’s own
hits like “Daddy’s Come Around,” “Seein’ My Father In Me,” and more.
On Country Cruising, Paul brings that legacy to life as host of our intimate Songwriters Rounds. Stripped of production and pretense, these sessions are just voices, guitars, and the real stories behind the songs—shared by the people who lived them. With Randy Travis joining the voyage, guests are invited into a rare, full-circle moment in country music history.
No barriers. No spotlight. Just master storytellers, honest conversation, and an exclusive, can’t-be-repeated experience found only on Country Cruising.
Returning this year, a fanfavorite experience at sea originated on Country Cruising. The Gospel Show brings together artists from across the Country Cruising lineup—voices you know and love—united by faith, soul, and shared purpose. Expect unexpected pairings, stripped-down performances, and moments that feel deeply personal.
Country Cruising is officially crossing the pond—and we couldn’t be more excited to welcome DJ Chris Armstrong from Northern Ireland, UK onboard!
Known for electrifying dance floors across Europe, DJ Chris Armstrong has built a global reputation for blending modern country hits, timeless classics, and crowd-favorite anthems into unforgettable party experiences. From boot-scootin’ line dances to late-night celebrations, Chris knows how to read a room and keep the energy high from the first beat to the last song.
His addition marks an exciting milestone for Country Cruising—proof that our country family stretches far beyond borders. With Chris onboard, guests can expect packed dance floors, nonstop fun, and a fresh global twist on the country music they love.
Country Cruising hits the other side of the pond—and the party just got bigger.
Returning by overwhelming demand, Whey Jennings’ Late-Night Jam is one of the most talked-about experiences on Country Cruising—and for good reason.
This after-hours session brings together an all-star mix of artists for an unforgettable, no-rules jam under the night sky. If you missed it last year—or couldn’t stay awake—you missed something truly special. This isn’t a scheduled show or polished setlist; it’s country music at its most authentic, spontaneous, and unforgettable.
Stay up late. Stay a little longer.
Because this is the jam everyone talks about long after the cruise ends.
Step onto the dance floor with Vaquera Vikki, one of the country music world’s most enthusiastic and experienced line dance instructors. With over 15 years of teaching under her belt, Vaquera Vikki brings energy, passion, and a love of dance that’s completely contagious.
Bootscootin’ Phil is back—raising the bar on your dance moves with engagement, comedy,
grace, community spirit, and high energy that just doesn’t quit!
Whether you’re a seasoned dancer or stepping into boots for the first time, Vaquera Vikki and Phil makes
every class fun, accessible, and unforgettable. From classic line dances to dynamic, partner, guests of all skill levels will find themselves smiling, moving, and making memories on the floor.
On Country Cruising, the connection goes far beyond the stage. Artists and guests share the ship—and the experience—together.
You might find yourself at the blackjack table with an artist, raising a glass during a whiskey tasting, or exploring a port on an artist-hosted shore excursion. These aren’t scheduled meet-and-greets—they’re real, spontaneous moments that happen when everyone cruises as one community.
It’s rare access, genuine connection, and country music lived beyond the spotlight.
Flying Dutchmen Travel | CST 20569170-40 | © Country Cruising All Rights Reserved
