If you play pickleball, you might want to take a look at one of the cruises I’ll be on later this month. I’ll be aboard Nieuw Amsterdam for the November 20, 2026, nine-day Southern Caribbean sailing, and it happens to be the first of five Holland America cruises with some extra pickleball fun on the schedule.
We’re talking time with the pros, opportunities to work on your game and a stop at Half Moon Cay, where four brand-new pickleball courts have joined the island’s list of things to do. The series wraps up in March with the Private Island Invitational, a professional event on those very same courts.
Now, you know I’ll have plenty to say about the food and everything else going on around the ship. But this gives us something else to check out, especially if you’re the person who hears “sea day” and immediately wonders whether you can squeeze in a few games.
Pickleball Has Been Around Longer Than You Might Think
Living in Florida, it sometimes feels like you can’t go anywhere without someone talking about pickleball. Somebody’s playing it, somebody’s learning it, and somebody’s trying to convince you to join them.
But even though it seems like it’s suddenly the biggest craze, the game actually goes back to 1965 when two guys from Bainbridge Island, Washington put the game together on an old badminton court with table tennis paddles and one of those perforated plastic balls. Eventually, professional equipment and rules were rolled out with the intent of creating something families could play together.
The growth has been pretty remarkable. About 4.2 million Americans played in 2020. By 2025, that number was 24.3 million, based on participation figures from the Sports & Fitness Industry Association. That’s a 479% increase in five years.
Part of the appeal is that you can get a game going without needing years of experience, and there’s a social side to it, too. You meet people, play a few games and suddenly you’ve got plans to do it again tomorrow. On a cruise, that’s a very easy way to make a few new friends.
You Can Play on Every Holland America Ship and Half Moon Cay
Holland America has at least one pickleball court on every ship in the fleet, so you don’t have to book one of these special sailings to play. The line is also the Official Cruise Line of the Professional Pickleball Association and Major League Pickleball.
If you’ve never tried it, paddles and balls are provided, and complimentary beginner lessons give you a chance to see what all the fuss is about. There’s no need to buy a bunch of gear before you’ve even figured out whether you like the game.
Already a player? Check the daily program or the Holland America app for open play and organized activities. Some sessions may require registration, so it’s worth looking at the schedule early.
You can keep playing when we get to Half Moon Cay. The island, now branded RelaxAway, Half Moon Cay, has four new pickleball courts in its sports area.
So if you’re traveling with someone who wants to spend the entire day on the beach while you’d rather get a game in, you’ve both got options. Play for a while, then head over to the sand and catch up.
Special Holland America Pickleball Cruises
The November 20, 2026 sailing I’ll be on kicks off four Countdown Cruises leading up to the Private Island Invitational. Across those countdown sailings, the plans include coffee chats and meet-and-greets with pickleball pros, trivia, onboard lessons and a pro clinic at Half Moon Cay.
If you already follow the sport, that’s a chance to spend some time around the people you usually watch play. If you’re just curious, you can see what interests you and work it into the rest of your vacation.
Here are the five sailings in the series:
| Departure | Ship | Cruise |
|---|---|---|
| November 20, 2026 | Nieuw Amsterdam | 9-Day Southern Caribbean |
| December 12, 2026 | Zuiderdam | 7-Day Western Caribbean: Greater Antilles & Mexico |
| January 2, 2027 | Eurodam | 7-Day Eastern Caribbean: Amber Cove & Bahamas |
| January 23, 2027 | Eurodam | 7-Day Eastern Caribbean: Amber Cove & Bahamas |
| March 7, 2027 | Nieuw Statendam | 7-Day Eastern Caribbean: San Juan & St. Thomas |
That last cruise is the one to look at if you want to attend the invitational itself. It’s scheduled for March 13, 2027, at Half Moon Cay, during Nieuw Statendam’s March 7 sailing, and brings professional players to the island as part of its 30th anniversary celebrations.
You’ll need to book that March 7 cruise and buy a separate event ticket to attend. Space is limited, with event tickets listed as coming soon, so keep an eye on the Private Island Invitational page for updates. The earlier countdown cruises have their own activities; they don’t include admission to the March event.
Playing Pickleball on Your Cruise? Here’s What I’d Bring
You’ve already got enough cruise packing decisions to make, so let’s keep this practical. With equipment available onboard, you can try the game without bringing much extra. If you’re planning to spend more time on the courts, here are 10 things worth making room for.
- Court shoes. Bring shoes made for court play and moving from side to side. Flip-flops aren’t acceptable footwear for game play.
- Lightweight workout clothes. Think comfortable shirts and shorts that dry quickly. Bring a change, too, because you probably won’t want to head straight to lunch in whatever you just played in.
- Extra athletic socks. They barely take up any room, and a fresh pair after a sweaty game is worth having.
- Your own paddle, if you’re attached to it. You can use the equipment onboard, but if you play regularly and have a favorite, bring it along. If you’re new, try the provided gear first.
- A cover for that paddle. Give it a little protection from your shoes, chargers and everything else rolling around in your bag.
- A refillable water bottle. Fill it before heading to the courts, and bring it ashore if you’re planning to play at Half Moon Cay.
- Sunscreen. You’re still out in the Caribbean sun, something so many people forget about until they look in the mirror later.
- A hat or visor that stays put. Try to bring one you won’t have to chase across the deck as it does get windy when the ship is at sea.
- Sunglasses that fit securely. The pair that slides down your nose every time you move probably isn’t the one for this.
- A small day bag. Something simple to hold your paddle, water and sun protection makes it easier to get everything to the courts, especially on your island day.
I’ll get a better look at the pickleball activities scheduled for the November 20th cruise once I’m aboard Nieuw Amsterdam, and I’ll share what’s happening, how to take part and what you can expect.
That’ll all be part of my daily cruise reports, along with the dining, the ports and the usual look at life onboard and how Holland America is bringing the game to this sailing.
