Enter To Win A 4-night Pickleball At Sea Group Cruise For Two

Celebrating 10 Years Of PlayTime Scheduler

To celebrate PlayTime Scheduler's 10th Anniversary, PlayTime Scheduler and Pickleball At Sea Group Cruise have teamed up for an incredible giveaway—one lucky winner will receive a 4-night Pickleball At Sea Group Cruise for two!

Pack your paddle and get ready for four unforgettable nights of Pickleball, sunshine, new friendships, and nonstop fun! Play Pickleball onboard AND ashore, enjoy Pro-led instruction and Open Play, join exclusive group activities, gather for Nightly Group Dinners, explore beautiful destinations, and make incredible memories along the way.

This isn't just a cruise with Pickleball. It's a Pickleball vacation at sea AND ashore!

Why Wait To Win? Start Planning Your Pickleball Vacation Now!

Ready to pack your paddle? Save $50 per Guest—that's $100 in savings for two Guests—when you reserve any upcoming Pickleball At Sea Group Cruise by October 31st, 2026, using promo code PTS10Year.

And here's the best part: booking now doesn't affect your chance to win! If you book now and are later selected as our Grand Prize winner, we'll apply the full value of your prize to the cruise you've already booked.

Pick your cruise. Pack your paddle. Let the countdown begin!

Learn More About Pickleball At Sea Group CruiseView Available Cruise Dates

Enter To Win A 4-Night Pickleball At Sea Group Cruise For Two!

More Than Just A Pickleball Cruise—A Complete Pickleball Vacation Experience

A Pickleball vacation shouldn't be limited to one place or one set of Pickleball courts.

With Pickleball At Sea Group Cruise, it isn't.

Every day takes you somewhere new—playing at iconic venues like The Fort in Fort Lauderdale, Florida and Baha Mar Resort in Nassau, Bahamas. And in between? You’re onboard a Royal Caribbean cruise ship—playing with ocean views in every direction.

It's the kind of variety and value no other vacation can match.

Pickleball onboard and ashore. Small-group, skill-based lessons with a Renowned Pickleball Pro. And all the fun, food, and entertainment of an award-winning Royal Caribbean cruise ship.

That's what makes Pickleball At Sea Group Cruise so special—and it's why our Guests keep coming back, year after year.

Schedule A Call To Learn MoreView Available Cruise Dates

  • Pickleball Onboard

    Reserved court time. Pro-led lessons. Open play. Off-court Pickleball seminars. Whether you're brand new to the game or a seasoned competitor, sessions are grouped by skill level, so everyone's playing at the right pace—with plenty of opportunities to sharpen your game and make new friends.

  • Pickleball Ashore

    From the official home of the APP Tour to stunning Caribbean resorts and one-of-a-kind local venues—our Exclusive Local Pickleball Experiences Ashore are a highlight of every cruise. Your Pickleball Pro joins you on the courts for dedicated lessons tailored to your skill level, with time to explore the destination through an included local tour and round-trip transportation.

  • Vacation Experience

    The fun doesn't stop when the Pickleball does. Enjoy world-class dining, Broadway-style entertainment, resort-style pools, and plenty of time to simply relax at sea. Then gather for Nightly Group Dinners and social events with a small group of new friends who love the game as much as you do.
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Past Guest Testimonials

  • "(Pickleball Pro) was energetic and his instruction drills were outstanding. He went out of his way to make it fun and engaging." - Past Guest, September 2026

  • "I had pretty high expectations going in and Pickleball At Sea Group Cruise exceeded every one of them. I’m already looking to book the next one." - Past Guest, September 2026

  • "(Pickleball Pro) provided great instruction and was accessible for interaction throughout the trip. I loved having the opportunity to watch him play, and play with him a bit. He made it fun and positive for everyone, regardless of their level of play." - Past Guest, February 2026

  • "More Pickleball than I was expecting. Loved it!" - Past Guest, February 2025

    "Amazing experience! We already rebooked." - Past Guest, November 2024

  • "Traveled with a group of Pickleball friends, we had the best time! Thank you for everything!" - Past Guest, November 2024

    "(Pickleball Pro was) Very personable, attentive, took the time to teach, to demonstrate to you what you were doing wrong in the lesson…highly qualified and professional. Related well with the players." - Past Guest, November 2025

  • "Activities were well planned out and executed. Instruction from an accomplished Pickleball Pro, and playing internationally, is an experience I'll never forget and hope to enjoy again!" - Past Guest, February 2026

    "LOVED being able to play Pickleball on the ship and in port. Really unique experience!" - Past Guest, February 2024
More Past Guest TestimonialsView Available Cruise Dates

NO PURCHASE NECESSARY. Open to legal residents of the 50 U.S. and D.C., 21+. Ends 10/31/26 at 11:59 PM ET. Prize excludes cruise taxes, fees, and port expenses, which are paid by the winner. ARV $2,601.72. Entry includes subscription to Pickleball At Sea Group Cruise emails, and entrant info may be shared with marketing partners; unsubscribe anytime. Void where prohibited. See Official Rules at www.pickleballatseagroupcruise.com/pages/official-sweepstakes-rules-playtime-scheduler-10th-anniversary-sweepstakes.