Wynonna Judd will be part of a multi-generational cast of country stars leading the 2027 Country Music Cruise, a seven-day voyage promising nonstop live music, themed nights and fan experiences at sea. The sailing runs February 7–14, 2027 aboard the Celebrity Silhouette, departing Ft. Lauderdale with stops in San Juan and St. Maarten. Cabin sales open to the public today.
Star-studded lineup aims to deliver nonstop country
The cruise bills Clint Black, Wynonna Judd and Joe Nichols as headliners among a broad lineup that spans veteran hitmakers, bluegrass favorites and contemporary country performers. More than 100 live performances are planned across multiple stages, with appearances slated from The Bellamy Brothers, Neal McCoy, Jimmy Fortune, Rhonda Vincent and Darryl Worley, plus tributes and specialty sets.
Programming highlights include Grand Ole Opry at Sea, All-Star Jams and a Waylon Jennings tribute featuring Tommy Townsend and Jerry Bridges. A range of acts from across the genre will also perform, including Moe Bandy, T. G. Sheppard, Billy Dean, Wade Hayes, John Berry, The Isaacs, The Malpass Brothers and several ensemble projects and tribute groups.
Fan experiences and philanthropy at the heart of the voyage
Beyond concerts, the cruise will offer a packed slate of fan-centric activities: meet-and-greets, Gospel Hour, line dancing, cornhole tournaments and themed evenings across eight dining and entertainment venues aboard the ship. Host Nan Kelley will guide many of the onboard events and special presentations.
The sailing continues its fundraising relationship with the Country Music Hall of Fame and Museum, with guitar auctions and other onboard initiatives that have raised more than $140, 000 in recent years. Organizers expect another sellout as fans flock to what is described as a floating country music festival with a packed schedule of performances and interaction opportunities.
Other cruises underscore country’s appeal at sea
Country-themed voyages beyond this sailing are also staking out 2027 as a big year for fans. A separate anniversary cruise this spring will feature Randy Travis as a special guest on a Celebrity Summit sailing in April 2027. While no full vocal set is anticipated from the country legend, he is slated to make appearances throughout that voyage alongside performers including James Dupré, Craig Morgan and Paul Overstreet.
Previous sailings of country-focused cruises have drawn thousands of attendees and packed schedules that included rum tastings, poker tournaments, live podcasts, shore excursions and hosted events with high-profile emcees. Prices for those itineraries have started in the low thousands per person, and advance bookings often fill quickly.
With Wynonna Judd on the roster for the February 2027 Country Music Cruise, organizers are leaning into a multi-generational approach that pairs legacy performers with contemporary favorites and specialty tributes. Fans seeking a week of live country music, interactive programming and charity-driven events will find the cruise a concentrated celebration of the genre at sea.