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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!

Lauren Jo Black

| Posted on

June 24, 2025

8:00 pm

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.

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.

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.

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.

Written by

Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for Answers.com and her work being featured on Forbes.com. She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.