Pickleball power play: How one advisor turned a hobby into a thriving travel niche

Christine Wilson didn’t set out to become a pickleball-planning prodigy.

But somewhere between a Florida holiday and a cold Ontario winter with nowhere to play, she found herself at the centre of one of travel’s most unexpectedly joyful trends: vacations built around a paddle, a perforated ball, and a whole lot of camaraderie.

Wilson, an Envoyage travel advisor based in Owen Sound, ON, has been in the travel industry for 17 years. Cruises, Europe, all-inclusives—she’s done it all.

But it’s pickleball, of all things, that has given her career a second wind. Not a light breeze. A gust. The kind that carries 80 people to resorts and arenas with paddles and shared enthusiasm.

Her origin story is delightfully unassuming. While visiting Florida with her husband one winter, Wilson discovered pickleball, a sport often described as a mash-up of tennis, badminton, and ping-pong.

It hooked her instantly. Back home in Owen Sound, however, there was one problem: nowhere to play. So, she did what any resourceful person might do. She started a club.

Today, that club has more than 200 members.

That alone would be enough of a story. But Wilson didn’t stop there. 

A collaboration with the Taylored Pickleball Academy opened the door to something bigger: curated pickleball trips.

Game on for group travel

Her first excursion, about two and a half years ago, took a group to the Caribbean. It worked. Then it really worked. Soon she was running four to five trips a year, each drawing anywhere from 40 to 100 players of all abilities.

Not bad for a niche that didn’t exist in her original business plan.

“It’s opened up an entirely new client base, people who are active, social, and a genuine pleasure to work with,” Wilson says. “It’s also brought a more experience-driven focus to my business, leading to strong relationships, repeat clients, and new partnerships, including booking travel for one of the teams in the Canadian National Pickleball League.”

That experience-driven angle is key. These aren’t just holidays where people happen to play a bit of pickleball on the side. The sport is the backbone of the itinerary. Days are structured around clinics, games, and tournaments, balanced with enough downtime to remind everyone they are, in fact, on vacation. And the settings? Not exactly your local rec centre.

In Mexico’s Mayan Riviera, Wilson’s groups have played at the Grand Palladium, a resort she praises for its “incredible sports facilities,” where staff wait courtside with cold towels.

In Croatia, she organized a trip to Split that combined pickleball with a chartered ship.

Other destinations have included Italy, Costa Rica, the Dominican Republic, and Greece. There was even a voyage with Crystal Cruises from Manila to Seoul. The ship had an onboard court. “You can bet we were out there!” she says.

It’s slightly surreal, but that’s part of the appeal. Pickleball, for all its explosive growth, still carries a sense of novelty. It’s approachable, a little quirky, and above all, social.

“What really stands out is the community,” Wilson says. “People are welcoming and likeminded. You can show up almost anywhere and feel included.”

“That’s why it pairs so well with travel. It gives people a shared purpose, and it’s such an easy way to connect with others, whether you’re travelling with a group or meeting people along the way.”

That sense of belonging travels well. In fact, it might be the secret ingredient that makes Wilson’s trips so successful. Strangers arrive with paddles and leave with group chats, inside jokes, and plans to book the next trip together.

A winning niche

Of course, behind the scenes, it’s not all perfectly executed drop shots. 

Coordinating groups of up to 100 people is no small feat. Flights, accommodations, court bookings, skill-level matching. It’s a logistical puzzle that would make some advisors quietly back away. But Wilson leaned in.

“It’s strengthened my group travel expertise in a big way,” she says. “I’ve learned how to manage complex logistics, communicate clearly with large groups, and stay highly organized.”

It’s helped her focus on creating shared experiences for clients, whatever their passions may be. These days, Wilson has shifted slightly away from massive groups toward more personalized experiences for pickleball clubs, friends, couples, and families.

It’s a strategic move that allows her to focus on service without losing the magic that made her pickleball trips special in the first place.

Meanwhile, the sport itself shows no signs of slowing down in Canada. “Pickleball continues to grow at an incredible pace across Canada,” Wilson says. “Over the past year, I’ve seen a big increase in participation at all levels, more clubs, more organized play, and more people looking to improve through clinics and tournaments.”

Meanwhile, in Owen Sound, a state-of-the-art facility is now under construction, and Wilson’s husband has been hired as general manager. It’s fair to say the couple is all in.

Wilson didn’t just spot a trend. She built a community. And then figured out how to put it on a plane.

This article originally ran on May 6, 2026, as part of PAX's annual "10 Most Fascinating Travel Advisors" list to mark Travel Advisor Appreciation Day. To read the full feature, click here. 

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