Win a Five-Night Cruise for Two on Boots on the Water!

Enter for your chance to win this unforgettable at-sea getaway with a slew of country music hit-makers!

By

Lauren Jo Black

| Posted on

June 24, 2025

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8:00 pm

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Boots on the Water Sweepstakes

Get ready for the ultimate country music getaway! We’re giving one lucky winner and a guest the chance to set sail on Boots on the Water, a five-night cruise experience happening February 13 through February 18, 2026. Sixthman, a pioneer in music festivals at sea for over 20 years, and Vibee, Live Nation’s premier music-led destination experience company, are bringing back Boots on the Water for its highly anticipated second sailing. 

Sweepstakes Ended: Winner Will Be Announced Soon!

Sailing from Tampa, Florida, the cruise will visit the stunning ports of Costa Maya and Cozumel, Mexico aboard the Norwegian Jewel, where guests can book unforgettable excursions, from exploring ancient Mayan ruins to snorkeling in crystal-clear waters or simply relaxing on a sun-soaked beach. And the best part? It’s all set to the live soundtrack of some of country music’s biggest stars.

Boots on the Water 2026
Boots on the Water 2026

Superstar Lineup

The incredible lineup features performances from Clint Black, Terri Clark, Diamond Rio, Chris Cagle, David Lee Murphy, Deana Carter, and Sarah Gayle Meech, plus unforgettable songwriter sessions presented by The Listening Room. 

Guests can also enjoy unique themed activities and experiences like Boot Scoot USA, Shut Up & Dance, Full Throttle Yoga, and even get inked at Liberty Tattoo while onboard.

Norwegian Jewel
Norwegian Jewel

In addition to the Country Music experiences on board, guests will also be able to enjoy all the amenities The Norwegian Jewel has to offer, including delicious dining options, the Jewel Club Casino, the Mandara Spa, the Body Waves Fitness Center, and more.   

One Grand Prize Winner Will Receive:

  • One (1) Ocean View cabin for two (2) on Boots on the Water sailing Feb 13-18, 2026 
  • Travel stipend covering up to $1400 to cover round trip flights and hotel for Winner and guest to Tampa, FL provided by Sixthman
  • Admission to all onboard concerts (all shows are general admission/non-ticketed)
  • All onboard meals at open seating dining areas
  • Entrance to the ship hot spots like the casino and disco
  • Use of ship pools and hot tubs
  • Use of ship health and fitness center
  • Prepaid port taxes and ticketing fees.

The approximate retail value (“ARV”) of the Prize is $4,948. 

Boots on the Water
Boots on the Water

Following the success of the inaugural 2025 cruise—which featured 10 superstar artists, 11 top country songwriters, and nearly 2,000 fans—Boots on the Water 2026 promises to deliver another unforgettable experience.

Fans can learn more about Boots on the Water, and reserve a cabin at www.bootsonthewatercruise.com.

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Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.