The Art of Herding Pickleball Cats: How to Nail a Group Trip Without Losing Your Mind

Travel

Aug 12

Tips, tricks, and sanity-savers for your next pickleball getaway

Did I mention that I went to Picklecon last weekend? There were many vendors, but one category that stood out was the pickleball travel companies. Aptly named Pickleball Travel, and VibeGetaways were two that stood out.

If you’ve ever thought that traveling to paradise with your crew from your local courts would be a blast, then booking a group pickleball trip can be a great idea. The trick is knowing what you’re getting into—and finding the right travel pro to help make it smooth.

The Weight of the Whistle (a.k.a. Responsibility)

When you’re the organizer, every decision feels magnified:

Location: Does it have enough courts? Are they pickleball-specific, or will you be dodging tennis lines?
Budget: Your friend who plays with a carbon-fiber paddle might be fine with a luxury resort, but the rest of the group may prefer something more modest.
Schedule: Between tournament-style play, group dinners, and free time, there’s a lot to juggle.
Logistics: Airport transfers, room assignments, court reservations—yes, you’ll get questions about all of it.

It’s fun, but it’s a lot. And unless you have a secret degree in hospitality management, it’s easy to get overwhelmed.

Enter the Group Travel Agent

A good group travel agent can save your sanity. They’re part matchmaker, part negotiator, and part firefighter (metaphorically—though hopefully not literally). Here’s what to look for:

Experience with Sports Groups: Ask if they’ve handled trips for tennis, golf, or pickleball before. They’ll understand the need for court time and group coordination.
Vendor Relationships: Agents with connections can get better rates, perks like welcome receptions, and priority booking for courts.
Custom Itineraries: Some agents specialize in cookie-cutter packages. Others will tailor every detail to your group’s vibe—pickleball in the mornings, wine tasting in the afternoons, sunset beach dinners at night.
Clear Communication: You want someone who responds quickly, keeps track of everyone’s questions, and gives you timelines so nothing slips through the cracks.

How to Find the Right One

Referrals: Ask your club or local pickleball community who they’ve used. Word-of-mouth recommendations are gold.
Pickleball-Specific Agencies: Yes, they exist, like the ones I mentioned earlier. These specialists know the resorts, destinations, and seasonal sweet spots for prime court availability, as well as other activities and excursions.
Interview Them: Treat it like hiring for a job—because that’s exactly what it is. Ask about past trips, group sizes they’ve handled, and how they deal with last-minute changes.

Your Role After Hiring an Agent

Hiring an agent doesn’t mean you’re off the hook—it means you shift from doing everything to making the big calls. You’ll still be the group’s point of contact for preferences, questions, and the occasional mild panic (“Can I bring my cousin’s friend’s neighbor?”). But instead of juggling 27 confirmation emails, you’ll just forward them to your agent and go back to working on your backhand.

Bottom Line

A group pickleball trip is one of the most fun ways to combine travel, sport, and friendship. But the bigger the group, the more moving parts there are—and that’s where a great travel agent earns their keep. Pick the right one, and you’ll spend less time chasing hotel contracts and more time chasing balls on a sun-drenched court.

Eric Cohen