If you've ever wanted to go on a pickleball getaway, now might be your chance. Thanks to our partnership with the Global Pickleball Federation, we're offering you the chance to join the Ultimate Pickleball Adventure on a beautiful IWorld of Travel pickleball cruise.
In our biggest-ever giveaway, one lucky reader will get the opportunity to score a free cabin on a boutique discovery ship, the Elysium. They'll sail through the Greek Islands on July 25 or August 15, 2025.
Keep reading to learn more about this huge giveaway.
What does the winner get?
I was invited to join this amazing pickleball cruise to Greece but, with a new baby at home, I can't go! So, I decided to give my spot away to one lucky Pickleheads reader. Here's what you'll win:
- A cabin aboard the boutique discovery ship, Elysium.
- Daily pickleball play with pro coach Smiley Riley.
- Exclusive training clinics with VIP pros like Matt Manasse.
- Pickleball matches on stunning land and sea courts.
- A tour of the idyllic Greek Islands.
- World-class Mediterranean dining and beautiful island views.
Read more details about this giveaway at IWorld of Travel.
When does the giveaway end?
The giveaway runs from February 18 to March 7. The winner will be announced on March 10, 2025.
How do you enter?
To enter the draw, just show us your app. Here's what you need to do:
- Download the Pickleheads app (if you haven't already).
- Register and take a screenshot.
- Submit your entry below.
Win a pickleball cruise!
Play pickleball on the top deck, train with VIP pros, and explore Greece. Enter before March 7, 2025 for your chance to win my cabin, valued at $11,000!
Who is IWorld of Travel?
IWorld of Travel is a New York-based luxury travel advisor founded in 1967. They specialize in free independent and group travel, working exclusively with advisors and partners in over 80 countries.
Who is Smiley Riley?
Riley Palmer, also known as Smiley Riley, is a top certified pro pickleball coach who also runs incredible pickleball trips. She prides herself on her excellent personalized coaching style that always comes with a big, positive smile.
What is the Global Pickleball Federation?
The Global Pickleball Federation (GPF) is the world governing body for pickleball, championing players of all ages, skills, and backgrounds, and the grassroots growth of the sport worldwide. We partnered with the GPF to give players free access to the world's most comprehensive court database.
The GPF is one of the main champions behind getting pickleball into the Olympics and is tracking its course to the 2032 Brisbane Olympics. What's more, if you join the Elysium cruise, you'll get to visit the site of the original Olympic Games.
What if you don't win?
Even if you don't win the giveaway, we're still offering you the chance to go on this Greek cruise at a discounted price. When you register, we'll send you a discount code for $400 off ($200 per person) per cabin. So, you can still join Smiley Riley and fellow players as they sail the Mediterranean this summer.
Good luck to all who enter! I'm looking forward to finding out who takes my place on this pickleball adventure. If you'd like to see more getaways like this, check out my list of the best pickleball vacations in 2025, covering a wide range of choices for players of any budget and skill level.
