Pickleball Vacations

By Matthew Schwartz

June 20, 2024

(Pickleball in Paradise players at Sandals South Coast, Jamaica)

You’re addicted to pickleball and have a wonderful, romantic getaway planned with your significant other. But as the vacation approaches, you’re in a panic. You break out in a cold sweat every time you think about your itinerary because of a glaring omission.

 No pickleball! What am I going to do without it? How am I going to survive the week? How can I go two straight days without playing?  Heck, one day without?

Thanks to savvy travel agents and entrepreneurs, you can go on a wonderful, romantic vacation while fulfilling your pickleball Jones and play every day if you wish. Numerous travel agencies looking to take advantage of the pickleball craze are offering pickleball themed vacations to five-star resorts in exotic locations. The vacations are another example of pickleball’s explosion in popularity.

“During the pandemic, I fell in love with pickleball,” Barb Strait says. She’s like millions of others who fell hard for this game with the funny name around the same time. Barb has been in the travel business since 2012. She owns Straightaway Travel, one of several companies offering pickleball vacations. During the COVID-19 pandemic, besides becoming addicted to playing pickleball, she had an idea.

“Once the Caribbean opened to travel professionals in 2020, I went [there] as much as I could,” she told me. “While in the Caribbean, one resort had pickleball courts and I thought, ‘how fun would it be to build a group trip for people who want to travel and love pickleball.’”

Barb formed a subdivision of Straightaway Travel and named it Pickleball in Paradise. She hosted a group of approximately 28 travelers to the Sandals South Coast resort in Jamaica in October 2021. It was a sellout. She led four trips the following year. Three of them sold out. In 2022, she brought on a woman named Elizabeth Higginbottom, who was the teaching pro at a private country club near Boone, NC, to run Pickleball in Paradise. The group went on 12 trips in 2023 and in 2024 is scheduled to host 20 groups by year’s end.

Barb says, “We work very closely with Sandals and Beaches resorts to build very happy groups that meshes our vision of Pickleball in Paradise with their gorgeous resorts.  We are working with them to build more and more courts across the brand. We know how many courts are at each resort and plan accordingly. You can’t have more people than court space.”

Barb describes a typical day: “We meet at the courts a little before 8 for a light breakfast and coffee. We then train and play from 8am-11am. The afternoon is free to relax at the beach, have cocktails at the swim up bar, paddleboard, snorkel, kayak, get a massage, whatever you would like to do!  We communicate on the Whats App and many people will message about meeting after dinner to play pickleball under the lights.  Some will go to see the band on the beach and others will hit the court again!”

Prices range from $1800 per person to $3700 per person for a week at a five-star resort in Turks and Caicos. Some guests extend their trip or upgrade to a butler room.

Tim and Natalia Smith of Edmund, OK, have gone on three trips with Pickleball in Paradise. “They always host the trips at great locations where there is a lot to do,” Tim emailed me on Tuesday from Alaska, while he and Natalia were on a Pickleball in Paradise cruise.  Pickleball on the cruises is played on indoor courts due to the high winds. Tim, 51, says he and Natalia, 45, enjoy “Pickleball in the morning, fun and sun in the afternoon - what could be better! We always take away at least one great tip from each clinic. Some of the things we have learned have really transformed our games and helped us to reach the next level.”

Some couples attend even though one spouse doesn’t play pickleball. Strait says there are plenty of activities for non-players. “The [non-playing] spouse can sleep in, get a massage, take a yoga class, paddle board,” Strait says.

Kelly Hill, 68, of Palmetto, FL, didn’t play on two pickleball vacations due to recent knee replacements. “While my husband played pickleball, I enjoyed reading, people watching on the beach, relaxing, getting into the pool and spending my time in the gorgeous settings,” Kelly said. “The Sandals staff and head pros did a great job making sure everyone on the trip had a great time.”

Kelly’s husband, Peter, said, “Pickleball in Paradise perfected the art of inclusion in their events so that Kelly always felt part of the group, even though she wasn’t on the courts.”

Another company offering pickleball vacations is called Pickleball Trips. It’s owned by Jon Moore and his brother Daniel, a 9-time national pickleball champion who introduced the sport to Japan. The company’s first pickleball themed trip was to Japan in 2016. After playing competitive tennis for most of his life, Jon officially made the switch to pickleball in 2018. Jon says since then the company has led close to 100 trips. Among the destinations:  Belize, Guam, Italy, Thailand and Montana.

“Each trip is completely different, but all our destinations offer plenty of cultural excursions outside of pickleball,” Jon said. “We've had people go fly fishing and whitewater rafting outside of Glacier National Park on our Wild Montana tour, organize a full-day scuba diving trip to the Blue Hole in Belize, or go golfing in places ranging from Mexico to Central Japan.”

Jon says his company’s trips tend to cost between $3000 and $4000 per person for double occupancy, with an average supplement of about $800 for solo travelers. “That price includes 4-star plus accommodations, almost all meals, professional pickleball instruction, all non-pickleball activities, and domestic transportation. The only thing that's extra is airfare to and from our starting point,” Jon said.

“Another thing that makes us unique is our connection to the global pickleball community,” he said.  “We design all our trips through and around local partners because we know we can't be experts on every destination. In essence, the existing, local pickleball community, along with their court situation, is what determines our destinations rather than starting with a destination and trying to throw together the pickleball. This approach allows us to offer the best possible experience, both on and off the court.”

Jon says his company’s trips are capped at 16 players with one instructor/tour host for every eight participants. Both companies, Pickleball Trips and Pickleball in Paradise, welcome everyone from complete beginners to advanced players.

If you’re thinking about taking a pickleball vacation, Jon offered this advice: “First, don't just go with the cheapest option. While it may be a cliche to say that you get what you pay for, it's usually true. Second, find out how long they have been in operation. The trip might be hosted by a well-known pickleball player or even pro, but they often have zero experience in the travel industry. Along those same lines, ask to be connected with a previous participant or two to hear their honest opinion about the experience. If they don't rave about the trip, there might be a better option!”

(Pickleball Trips vacationers playing at the Wataview resort in Belize)

Thoughts of the week, not all pickleball

-Rest in peace, Willie Mays. The “Say Hey Kid”, who died Tuesday at 93, was the greatest baseball player I ever saw. He hit 660 career home runs and at 5’10”, 170 pounds he did it without steroids, and he missed 266 games due to Army service. I was lucky to have seen him play in person several times. I was 18 and in New York’s Shea Stadium for Willie’s Mets debut on May 14, 1972. All he did was hit what proved to be the game-winning home run. And against the San Francisco Giants no less, the team he had played for since 1951.

-The pickleball paddle industry’s unprecedented recent success has led to an unprecedented major problem being called by some “The great de-listing controversy.” Several recently released paddles have been removed, banned, de-listed or whatever you want to call it by USA Pickleball from the approved list allowed in USA Pickleball sanctioned tournaments. USA Pickleball claims that the paddles “did not meet testing standards.” There has been a growing concern that the paddles are too powerful and thus dangerous. Jason Flamm wrote so well about this on The Dink Pickleball’s website.

In The Dink Pickleball’s podcast, PicklePod, pro player Travis Rettenmaier, discussing dangerously powerful paddles, said, “This will be the demise of pickleball, if things like this are not outlawed, because a poor little girl in Crescent is gonna get hit in the face at 112 miles per hour and she's not gonna come back.“

-In response to the de-listed paddles, the company for which I write this weekly blog, Hudef Sport, issued the following statement on social media:

We have learned that some merchants suffered losses due to the recent removal of paddles from USA Pickleball. HUDEF will try its best to help all merchants who suffered losses to minimize their losses. If you are interested, please write an email to us: sales@hudefsport.com. Please include your phone number and business name. Thank you.

That gesture makes me proud to write for Hudef.

-I don’t want to get preachy here but if sharing my experience helps one person then mentioning this will be worth it. In 2018 I was suffering increasing pain in my hands and fingers and had to see a rheumatologist. The doctor never brought up anything about diet or nutrition, he only prescribed pills. They didn’t help. Then one morning, after a night of eating pizza, I could not make a fist. I could not hold the steering wheel to drive. I had read some articles over the years about dairy being an inflammatory but still ate it until that morning I couldn’t drive. I quit dairy that day. Three weeks later, the joint pains vanished and I have had none since. I don’t miss dairy and the plant-based alternatives taste good. I later quit meat, too, and have never felt better.

-The city of Asheville, NC, still has not one dedicated public pickleball court. Without warning on May 24th, the city’s parks and recreation department removed its nets from all of its courts (which are also lined for tennis). The department said some pickleball players failed to roll the heavy duty nets off to the side, and the wheels left divots in a couple of recently resurfaced courts. The department did not provide replacement nets and  pickleball players need to bring portable nets to the courts or rent one from the city.

None of this would be happening if the city had dedicated pickleball courts with permanent nets installed. It’s an embarrassment for a city of 95,000 that’s consistently ranked among the “best places to retire.”

As I’ve previously written, the researchers who call Asheville a great place to retire must not play pickleball.