Pickleball on the High Seas
Holland America adds pickleball and events to its cruise itineraries
By Alexandra Sinopoli
October 7, 2026 • 7 min read
For many pickleball players, the sport has become much more than something to do for an hour or two on a weekend. It has become a way to meet people, stay active, travel and, in some cases, plan an entire vacation around.
As pickleball continues to find its way into more hotels, resorts and travel destinations, Holland America Line has been building the sport into its cruise experience.
Since 2022, the cruise line has been the exclusive cruise line partner of the PPA and Major League Pickleball (MLP), and pickleball courts are available across the fleet. Guests can pick up a paddle and play while enjoying a regular Holland America cruise, making the sport part of the everyday onboard experience.
The experience expanded in 2025 when Holland America added dedicated pickleball courts at RelaxAway, Half Moon Cay™, its private island destination in the Caribbean.
Beginning in 2026 and continuing into 2027, Holland America is introducing four Countdown Cruises featuring PPA player appearances, exclusive onboard programming and opportunities to play at Half Moon Cay. Guests can participate in experiences such as coffee chats with pro players, trivia and organized pickleball activities.
Then, in March 2027, Holland America will host the Private Island Invitational, an exclusive professional pickleball competition at RelaxAway, Half Moon Cay, during a special Caribbean cruise.
According to Joe Chantry, Vice President of Entertainment & Enrichment at Holland America Line, the partnership developed naturally as the popularity of pickleball continued to grow.
“We’ve seen that enthusiasm firsthand on our ships. It’s actually one of the most popular sports among our guests.”
For Holland America, the connection goes beyond the number of people picking up paddles. The company sees similarities between the community surrounding pickleball and the social experience of cruising.
“At their core, both are about connection,” Chantry said.
A pickleball game can start with four strangers and end with four people exchanging names and making plans for another game. Cruising creates a similar environment, with guests spending several days sharing meals, activities and excursions.
“Pickleball is incredibly social,” Chantry noted. “It brings people together, sparks conversation and creates moments of fun. Cruising does the same thing.”
More Than Just a Court
When people hear “pickleball cruise,” it would be easy to imagine a week filled with nonstop games. But Holland America’s approach starts with something simpler: giving guests a place to play while they are already on vacation.
The courts across the fleet mean guests do not have to be highly competitive players or book specialized sailings to participate. Casual players can grab a paddle and join a game, while regular players can make the court part of their normal routine at sea.
The Countdown Cruises add another layer with PPA player appearances, exclusive activities and opportunities to interact with the pros.
“You can expect a lot more than just time on the court,” Chantry added.
Holland America wants the programming to appeal to a wide range of players.
“If you’re a passionate player looking to sharpen your game, you’ll have opportunities to learn,” Chantry explained. “If you’re newer to pickleball or simply enjoy playing for fun, there will be plenty of opportunities to participate in a welcoming environment.”
A competitive player could participate in a professional-led clinic, while someone newer to the sport could take a beginner-friendly lesson. Other guests might simply want to play casually.
The goal is not to turn a vacation into a weeklong tournament. It is to make pickleball another way guests can enjoy the vacation.
A Day at Sea
There is no single schedule that will define a day on one of the special sailings, but Chantry offered a glimpse of what guests can expect. On the Countdown Cruises and Invitational sailings, the experience also includes opportunities to interact with professional players.
On those sailings, the morning could start with open play or a clinic, followed by an opportunity to talk with one of the professional players. Guests could then explore a port, relax on the ship, try one of the restaurants or return later for another pickleball activity or social event.
“You might start the morning with open play or a clinic, spend some time chatting with one of the pros, then enjoy everything else the cruise has to offer,” Chantry described.
The sport is woven into the vacation rather than becoming the entire reason for the trip. Chantry described the combination as “the best of both worlds: a great cruise vacation combined with pickleball.”
Unlike a tournament, a cruise also gives guests several days to get to know other players and interact with professionals. The extended setting allows the social side of pickleball to develop naturally.
Holland America
Matches Come with a View
Enjoy friendly games on courts overlooking the sea.
Improve Your Game at Sea
Complimentary onboard pickleball lessons for all.
Pack Less, Play More
Complimentary pickleball gear ready whenever you want.
Make New Connections
Connect, compete and create lasting memories.
Getting Closer to the Pros
One of the biggest differences between Holland America’s everyday pickleball experience and the special sailings is access to professional players.
Fans are accustomed to seeing PPA professionals compete on the court or following them online. A cruise offers a different kind of access because the athletes and guests are participating in the same overall experience.
Holland America says special programming may include professional-led clinics, lessons, meet-and-greets, coffee chats and other events.
“We’re thrilled to be working with some incredible talent from the PPA,” Chantry shared. “What excites me most is giving guests the chance to interact directly with some of the pros.”
Clinics give players opportunities to ask questions, see techniques up close and potentially receive feedback on their own games. Even for guests not seeking serious instruction, having a conversation with a professional player can make the experience more personal.
“It’s a much more personal experience than most fans would typically have at a tournament,” Chantry explained.
Taking the Game to the Caribbean
The evolution of Holland America’s pickleball program does not stop at the ship.
In 2025, the cruise line expanded the experience to RelaxAway, Half Moon Cay™, its private island destination in the Caribbean. Dedicated pickleball courts give guests another place to play while experiencing the island.
Instead of playing at a neighborhood recreation center or local park, players can step onto the court surrounded by a Caribbean destination and then spend the rest of the day enjoying the island.
“We’re always looking for ways to create experiences that guests can’t find anywhere else,” Chantry noted. “RelaxAway, Half Moon Cay™ is a perfect example.”
The expansion also reflects a larger trend in pickleball travel. Players are increasingly traveling for tournaments, clinics, camps and other events, while resorts and destinations are incorporating courts and programming into their offerings.
In March 2027, Half Moon Cay will become the site of the Private Island Invitational, an exclusive professional pickleball competition during a special Caribbean cruise.
The Invitational represents another step in the partnership. Holland America began by putting pickleball courts on its ships, then expanded the sport to its private island. The Countdown Cruises add specialized programming and PPA player access, while the Invitational brings professional competition directly to the island.
Why the Partnership Works
Holland America has been the PPA’s exclusive cruise line partner since 2022, giving the company several years to see how guests respond to the sport.
According to Chantry, the response has been strong. The cruise line has seen increased demand for pickleball across its 11 ships and has continued to expand its offerings.
What has surprised him most is how naturally the pickleball and cruise communities fit together.
“Honestly, it’s how naturally they fit together,” he observed.
Both place a high value on social interaction and shared interests. Pickleball becomes an easy conversation starter onboard because players already have something in common before they step onto the court.
The experience also accommodates different types of players. Serious players can focus on professional clinics and lessons, while recreational players can enjoy social play. Beginners can try the sport without feeling as though they are entering a competitive tournament.
The same flexibility extends to families and friends. Someone can be fully invested in pickleball while a travel companion participates occasionally or not at all.
Pickleball Sets Sail
As the sport continues to grow, pickleball is becoming part of how some players choose where to travel.
“Travelers increasingly want experiences that reflect their interests and passions,” Chantry said.
For someone who plays several times a week, follows pro tournaments and is part of a pickleball community, a vacation that incorporates the sport can offer something a traditional cruise might not. Instead of looking for a court after arriving at a destination, pickleball is already part of the cruise experience. On the Countdown Cruises, guests may also have opportunities to interact directly with professional players.
Ultimately, the appeal may have less to do with how many games someone gets to play and more to do with who they get to play them with as the court is only one part of the experience. The rest comes from the people around it.
Holland America’s timeline shows how quickly the expansion has happened. In 2022, pickleball became part of the cruise line’s fleetwide experience through its partnership with the PPA. In 2025, the sport moved beyond the ship to Half Moon Cay. Beginning in 2026, the Countdown Cruises add special programming and professional player appearances. In March 2027, the Private Island Invitational will bring professional competition to the private island itself.
Guests still have destinations to explore, food to try, entertainment to watch and time to enjoy being away. They do not necessarily have to choose between a pickleball experience and a cruise vacation because Holland America is finding ways to combine the two.
By bringing the PPA experience onboard and creating new ways to play at sea and in the Caribbean, Holland America is giving players another way to combine the sport they enjoy with the destinations they want to explore.
For pickleball players, the next game might not be at the local recreation center or the tournament down the road. It might be waiting somewhere between the ship, the sea and a Caribbean island. ●
About Alexandra Sinopoli
Alexandra Sinopoli is a media and communications student in her senior year at Arizona State University and an editorial intern with The Pickleball Weekly. Originally from Southern California, she has always enjoyed reading, traveling, and learning about new people and places. Alexandra previously wrote for The Moorpark Reporter, where she covered the performing arts, and has experience in journalism, social media, and content creation through her social media accounts. She especially enjoys travel and lifestyle writing and finding ways to make a story feel relatable to the people reading it. Outside of work and school, she’s usually planning her next trip, exploring somewhere new, or spending time with friends and family.
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