Boots on the Water Cruise Sweepstakes – Win a 5-Night Country Music Cruise for Two!

Ready to trade the dirt road for the open sea? Enter the Boots on the Water Cruise Sweepstakes for your chance to win an unforgettable five-night country music cruise for two! Set sail alongside an incredible lineup of chart-topping country music stars, where the waves meet the twang, and the party never stops.

Picture this: sunny days at sea, tropical destinations, and nights filled with live performances from some of the biggest names in country music. You'll enjoy intimate shows, jam sessions, meet-and-greets, and line-dancing under the stars—all while cruising in luxury.

This isn’t just a cruise; it’s a floating country music festival. Whether you're a lifelong country fan or just looking for the ultimate getaway, this is your chance to escape the ordinary and sail into an experience like no other.

Enter now for your chance to win the trip of a lifetime on Boots on the Water! Boots on, bags packed—paradise is waiting.

Limit: Only one entry is allowed regardless of method of entry. The minimum age limit to enter the giveaway is 18.

How to Enter in Boots on the Water Cruise Giveaway:

Online: During the Entry Period, visit countrynow.com and complete the online entry form by providing your name and email address.

Mail-in: To enter by mail, send a postcard including your full name, mailing address, phone number, and date of birth (mm/dd/yyyy format) to: Country Now x 2026 Boots on the Water Sweepstakes, PO BOX 280273, Nashville, TN 37228-9998.

Boots on the Water Cruise Sweepstakes Winner Selection:

One grand prize winner will be selected randomly on or about July 11, 2025 from all eligible entries.

Win A Country Music Cruise Vacation Giveaway Prizes:

One Grand Prize Winner will receive:

• One Ocean View cabin for two on Boots on the Water sailing February 13–18, 2026
• Travel stipend up to $1,400 for roundtrip flights and hotel to Tampa, FL (provided by Sixthman)
• Admission to all onboard concerts (general admission, non-ticketed)
• All onboard meals at open-seating dining areas
• Access to ship amenities including pools, hot tubs, casino, disco, and fitness center
• Prepaid port taxes and ticketing fees

(ARV: $4,948)