Paddles, Passports and Paradise
PickleballTrips.Net turns Caribbean getaways into memorable experiences
By Adriana Falco
October 14, 2026 • 10 min read
The Caribbean sun is climbing above the palms, and another day in paradise is beginning.
At a beachfront resort, pickleball players are warming up for a morning of drills, strategy sessions and friendly competition. Beyond the courts, turquoise water stretches toward the horizon, and the promise of an afternoon by the pool makes even the toughest workout a little more appealing.
By lunchtime, the paddles will be put away. Some players will head for the beach, others for the spa or a leisurely meal overlooking the ocean. A few might arrange another match, while new friends make plans for dinner or an excursion along the coast. Tomorrow, there will be more pickleball. Today, there is an entire Caribbean island to enjoy.
For Randy and Patty Penberthy, the husband-and-wife team behind PickleballTrips.Net, this combination of athletic activity, tropical travel and shared experiences has become the foundation of an unexpectedly successful business.
Through their St. Louis-based travel agency, RPAS Travel, the couple organizes group pickleball vacations at all-inclusive resorts throughout Mexico and the Caribbean. The trips bring together professional pickleball coaching, organized tournaments, luxury accommodations and the freedom to enjoy a destination at an individual’s pace.
Yet what makes their story particularly interesting is that neither Randy nor Patty originally intended to enter the pickleball travel business. Their journey began with a retirement plan, an unexpected question and a remarkably ambitious search conducted from their computers at home.
A Retirement Plan Takes an Unexpected Turn
In October 2023, Randy and Patty launched their travel agency. When it came time to name the business, they found inspiration in an unlikely place: the nickname of their savings account. RPAS stood for “Randy and Patty’s Alternative Savings,” and the couple incorporated those initials into the name RPAS Travel.
“The name doesn’t mean anything to anyone else,” said Patty Penberthy, co-founder and owner of RPAS Travel, “but we giggle a little every time people ask us about it.”
Randy had been planning his retirement for May 2026, and the couple envisioned a modest travel business that would allow them to explore more destinations while generating additional income. They were already enthusiastic travelers, particularly drawn to the warm weather and beachfront resorts of Mexico and the Caribbean. They also enjoyed playing pickleball, although the sport and their travel business initially existed as separate interests.
Then someone from their home pickleball club, where the couple’s agency sponsored a court, asked a question that changed their plans. Were there any resorts in the Caribbean with enough pickleball courts to accommodate a group vacation?
Randy assumed the answer would be relatively easy to find. It wasn’t.
He initially contacted several major hospitality companies, including Hyatt and Iberostar, hoping to identify properties with suitable playing facilities. The information proved surprisingly difficult to obtain. Online searches frequently produced questions from other travelers wondering whether resorts offered pickleball, but few reliable answers about the courts themselves.
The Penberthys could have abandoned the idea. Instead, they opened Google Earth.
Working from their computers, they began examining coastlines throughout the Caribbean, searching for and zooming in on what appeared to be clusters of pickleball courts at resort properties. The painstaking investigation eventually identified 17 locations that each seemed to have at least four pickleball courts.
Then came the remarkable part. In 2024, Randy and Patty packed their bags and traveled to inspect all 17 properties themselves. Their on-site visits revealed that finding a resort with pickleball courts would only be the beginning of a new venture.
A resort property might offer beautiful accommodations and a spectacular beach yet lack sufficient playing space to support a group of 50 or 60 enthusiastic pickleball players. Other resorts had courts but lacked the combination of amenities, organization and hospitality services the couple envisioned for their guests. Finding the right combination sometimes felt like finding a needle in a haystack.
The Penberthys soon began to evaluate destinations through two different lenses: the expectations of a vacationer and the practical needs and must-haves of a pickleball player.
Today, Pickleball Trips has identified 22 all-inclusive resorts that meet its criteria, selected from more than 1,500 properties across Mexico and the Caribbean.
Their search has also evolved into something larger than evaluating existing facilities. Working with various resort operators and experienced contractors, the couple encouraged the conversion of underused tennis courts into permanent pickleball courts.
Acting on their recommendations, Planet Hollywood in Cancun built eight new courts this summer to accommodate future pickleball group vacations and has already noticed an increase in occupancy rates. Apple Leisure Group Vacations (ALGV), along with the Hyatt Inclusive Collection of resorts, has also caught the vision and is encouraging several major hotel chains such as Krystal, Iberostar, and RIU, whose vacations they sell and package, to examine how they can leverage these pickleball groups to help fill their resorts.
A Vacation with a Built-In Community
Typically, a PickleballTrips.Net getaway brings together 48 to 64 pickleball players, a group size Randy considers manageable. Some participants arrive with spouses or friends. Others register individually, knowing little about their fellow travelers beyond a shared interest in pickleball. Approximately 70% are women seeking a Caribbean pickleball adventure with few worries.
Randy compares his organized trips to attending camp, where strangers spend several days sharing activities, building camaraderie and developing friendships.
He and Patty are particularly aware that guests arrive with varying expectations, playing abilities and personal circumstances. Both make a conscious effort to recognize those differences and accommodate their travelers.
Before departure, participants complete a survey about their playing abilities and interests. The information helps organizers develop appropriate activities, whether a guest wants to improve from a 3.0 to a 4.0 level or simply enjoy a few recreational games each morning.
Randy recognizes that traveling to play with unfamiliar people can be intimidating, particularly for beginners.
To address those concerns, the company has been developing several types of programming. Pickleball 101 introduces newcomers to the fundamentals, while Tournament Trail is designed for advanced players interested in more competitive experiences. The distinction allows travelers to choose an experience that reflects their goals rather than feeling pressured to keep pace with more experienced players.
Paradise Beyond the Courts
One of the attractions of a Pickleball Trips vacation is what happens after the morning matches end.
The afternoons are intentionally unstructured, giving travelers opportunities to enjoy the amenities that drew them to the Caribbean in the first place. Some head directly to the swimming pool. Others settle into a beach chair, explore the resort’s restaurants or book a spa treatment. Additional pickleball games often develop spontaneously, as players arrange matches with people they met earlier in the week.
Optional excursions, including sunset catamaran cruises, provide opportunities to explore beyond the resort. These off-property experiences generally involve an additional charge. Group dinners are also available, although Randy has observed that guests frequently organize smaller gatherings as friendships develop.
Randy believes balance is important. The company could fill every hour with activities, but doing so would leave little room for the relaxation and spontaneity that make vacations enjoyable. The all-inclusive format supports this flexibility. Guests can enjoy resort dining, beaches, pools and other amenities without continually coordinating separate arrangements. Properties with multiple restaurants also provide opportunities to explore different cuisines throughout the stay.
A New Opportunity for Pickleball Clubs
While PickleballTrips.Net vacations are open to individual travelers, the company also works with established pickleball communities. Club owners, facility managers, coaches and social group organizers can partner with the Penberthys to arrange vacations for their members.
Rather than expecting everyone to participate in every listed activity, the Penberthys encourage guests to become involved at their own pace. Their on-site concierges ensure that travelers have someone available when questions or concerns arise, while on-site pickleball professionals provide coaching and play appropriate to each guest’s ability, with opportunities to improve.
This personal attention to detail continues throughout the vacations, helping guests feel comfortable and well cared for.
The couple also attends the trips themselves, drawing on relationships they have established with resort general managers, front desk personnel, activities directors and group coordinators. If a guest discovers that a room assignment is incorrect or encounters another hospitality issue, the Penberthys can work directly with resort staff to address it.
This approach reflects their background as travel agents first and pickleball enthusiasts second. While coaching professionals oversee the instruction and competition, Randy and Patty concentrate on making the vacation experience run smoothly.
The Morning Belongs to Pickleball
For players interested in improving their games, the daily schedule offers considerably more than casual resort play.
Mornings generally begin around 7 a.m. with approximately 30 minutes of pickleball-specific fitness exercises and stretching. Participants then move into warm-up drills before working with coaches on technique, shot selection and strategy.
The instruction is organized into smaller groups, giving players opportunities to practice skills suited to their experience. Some drills concentrate on executing individual shots, while others focus on understanding when to use them during a rally. Coaches demonstrate techniques, explain strategic decisions and guide participants through exercises designed to reinforce what they have learned.
The atmosphere becomes more competitive as the morning progresses. King or Queen of the Court, Up and Down the River and short games against instructors keep participants moving between courts and playing with different partners. The variety creates opportunities for players to test new skills without turning every session into a formal tournament.
As the week advances, the competitive element increases.
Round robins typically take place near the end of the trip, followed by a tournament on the final full day. Depending on the group, the competition may feature mixed doubles, gender doubles or a combination of both. An awards ceremony, complete with medals, brings the organized tournament experience to a close.
By approximately noon, the structured programming is finished. Players who still have energy can arrange additional games during open play. Others are free to exchange their court shoes for sandals and enjoy the resort. Pickleball Trips supplies balls, ball hoppers, towels, hydration stations and morning fruit. Guests bring their own paddles.
Rather than requiring a club manager to coordinate hotel reservations, court access, instruction and group transportation, PickleballTrips.Net handles the planning. The concept creates an opportunity for clubs to extend their communities beyond their regular programming. Members who ordinarily see one another during open play or a weekly league can spend several days traveling, competing and socializing together.
For facility owners, the experience offers an opportunity to strengthen member relationships while giving players another reason to remain involved with their clubs.
Growing Beyond the Original Plan
What began as a modest retirement venture has developed into a business requiring increasingly long-range planning. PickleballTrips.Net generally begins promoting the vacations eight to ten months before departure. Randy says many of the trips reach capacity three or four months in advance.
The company had already placed deposits on 21 trips for 2027, reflecting both growing demand and the importance of reserving sufficient court time at desirable resorts. Its destinations include Cancun, Riviera Maya, Antigua, Punta Cana, Curaçao, Turks and Caicos, Los Cabos and other locations throughout Mexico and the Caribbean.
The Penberthys are also looking beyond the region that established their business. Randy has received interest from contacts in Greece, Croatia and Vietnam, although those possibilities remain part of the company’s longer-term ambitions rather than established destinations.
For the Penberthys, the possibilities are exciting, but expansion also brings practical challenges. Popular resorts must accommodate weddings, conferences and other organized groups, limiting the dates available for pickleball vacations. Court reservations must be arranged well in advance, and additional demand does not automatically translate into additional resort capacity.
The couple’s experience has taught them that selecting the right property matters more than simply adding another destination to the schedule. Their original Google Earth search may have been unconventional, but the attention to detail behind it continues to guide their decisions.
The Best Souvenirs Aren’t Always Packed
At the conclusion of a PickleballTrips.Net vacation, guests may return home with a commemorative T-shirt, tournament medal and photographs of Caribbean beaches. Some will have improved their backhands or developed greater confidence at the kitchen line. Others will remember an afternoon aboard a catamaran, a memorable dinner or the excitement of competing in a tournament far from home.
For Randy and Patty, however, the most meaningful part of the experience is often what develops between those activities. Randy sees pickleball as a way to bring people together who might otherwise never cross paths.
“We want them to walk away with that when they leave one of our trips,” he said, referring to the friendships and connections formed during the vacation. “We really concentrate on making people feel seen, heard, welcomed, and valued as a valued member of our global, connected pickleball community.”
The sentiment explains why the Penberthys remain personally involved in their vacations, even as the business grows. Randy says most groups return for additional trips, yet often choose a different destination. A vacation in Cancun might lead to another in Antigua, followed by Curaçao or a resort that has only recently introduced pickleball facilities.
The changing scenery gives returning travelers something new to discover, while familiar faces provide continuity from one trip to the next. For some participants, the attraction may begin with the promise of warm weather, beautiful beaches and several mornings of organized pickleball. By the end of the week, their favorite memories may have little to do with the final score.
A new friendship, an unexpected conversation or a shared adventure can become the experience they remember most. The Caribbean provides the setting. Pickleball brings everyone together. And somewhere between the first morning warm-up and the final evening’s farewell, strangers can become traveling companions who are already discussing where to go next. ●
About Adriana Falco
Adriana Falco is the Founder and Editor-in-Chief of The Pickleball Weekly, a global digital magazine reaching readers in over 100 countries across six continents. A pickleball player since 2012, she combines more than 30 years of executive leadership with a passion for storytelling that captures every facet of the sport. With a career from international technology companies to major news organizations, Falco covers the people, businesses, innovations, and global trends shaping pickleball’s future, with a mission to connect and inspire the worldwide pickleball community through credible journalism and compelling stories.
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