Nobody Wants to Be the One Herding the Paddle People.
We plan group pickleball trips that combine high-energy play, resort-level perks, and zero group chat drama. You bring the players—we’ll handle the rest: courts, travel, logistics, and VIP extras included.
You Love Pickleball. You Hate Group Logistics. We Get It.
We plan group pickleball trips that feel like a vacation—even for the organizer.
Who We Are
Vacationisms is a luxury travel agency that plans custom group pickleball trips to top-tier resorts across Mexico and the Caribbean.
We work with private clubs, social leagues, pickleball-obsessed besties, and tournament hosts who want their travel to match their game: smooth, competitive, and ridiculously fun.
As your luxury group travel advisor, we coordinate everything—from booking the perfect resort with dedicated courts to managing flights, transfers, and even non-player extras like spa appointments, welcome dinners, and sunset cruises. You’ll get a fully custom trip, a group booking portal, and concierge-level support from the first planning call to the last match point.
We’re here to make you look like a planning genius—without actually making you do all the planning.
What We Solve
📍 Too Many People, Not Enough Consensus
We simplify the chaos with tailored options, a booking portal, and no decision-by-committee drama.
🎾 Sketchy Court Situations
We only work with resorts where the courts are regulation, instructors are real, and the vibe is next-level.
📲 No Time to Organize Anything
We’ll coordinate the itinerary, transfers, spa time, dinners, and more—so the trip runs smooth from day one.
💸 Wasted Budget on Mediocre Trips
Our group pickleball trips come with upgrades, group perks, and exclusive resort access you won’t find online.
Types of Group Pickleball Trips We Plan
Whether you’re here for the rallies, the resort, or a little of both—we’ll tailor your group pickleball trip to match the vibe and the vision.
Pickleball + Paradise Getaways
For friend groups, social clubs, and rec players who want great games, beach views, and plenty of time by the pool between matches.
Milestone + Celebration Trips
Celebrate birthdays, anniversaries, or retirement in style—with high-energy play, private dinners, suite upgrades, and a little friendly competition.
Club + League Retreats
Perfect for teams and member groups looking for a change of scenery. We’ll handle the courts, flights, room blocks, and custom add-ons—so your only job is to show up and play.
Not Sure Where You Fit? Let’s Talk.
We’ll help you figure out what kind of trip makes the most sense—and then make it happen.
Book Your Complimentary Consult →
What Our Clients Are Saying
I planned a birthday pickleball trip for 20 of us, and Vacationisms made me look like a total rockstar. Great courts, gorgeous resort, and not a single logistics headache.
Our pickleball club trip with Vacationisms was seamless. From the court scheduling to the group dinners and transfers, everything just flowed. Already planning next year’s.
We had a mix of serious players and beach lovers—and somehow everyone was thrilled. Vacationisms got us great rooms, top-tier courts, and a spa day that sealed the deal.
More Paddle. Less Planning. That’s the Sweet Spot.
We’ll handle the courts, the travel, the upgrades—even the group dynamics. You just pack your paddle and show up.
See What’s Possible
Here’s a taste of how group pickleball trips should be done. From beachside rallies to island-style recharging, we build play-and-stay experiences that deliver way more than a good game.
Turks & Caicos Paddle + Paradise
5 nights | Beachfront Resort
• Daily court time + private instruction
• Group paddle clinic + sunset sail
• Private beach dinner + spa credits
Tulum Pickleball + Wellness
6 nights | Luxury Jungle Resort
• Pickleball courts + guided movement classes
• Smoothie bar, beach time + spa day
• Private chef dinner under the stars
Punta Cana Tournament
5 nights | All-Inclusive
• Court access + team tournament
• Group dinners + beach bonfire night
• VIP airport transfer + suite upgrade
What We Charge—So You Don’t Pay in Group Text Fatigue
Group pickleball trips sound fun… until you’re the one in charge of booking, coordinating, reminding, and fixing. That’s where we come in.
We charge a flat planning fee based on your group size and trip complexity. You’ll get hand-picked resort options, tournament-friendly logistics, and concierge-level support from first call to final point.
Here’s how it breaks down:
Group Travel Research & Design
Starting at $375
For groups of 10 or more pickleball travelers
You’ll receive:
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Three curated trip options tailored to your group’s vibe
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Two rounds of follow-up adjustments
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A custom booking portal for easy RSVPs
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Full itinerary access via mobile + PDF
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Limited on-site event coordination with resort staff
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24/7 emergency support during travel
Perfect for social groups, clubs, milestone trips, or anyone who wants to hit the courts without hitting their limit on logistics.
Planning Something Bigger?
Organizing for a large group, multi-destination itinerary, or club-wide event? We’ve got you. Fees may vary based on group size and complexity—but we’ll walk you through it all upfront. No surprises. No pressure. No court drama.
The Courts Are Calling. Let’s Make It a Trip Worth Talking About.
We’ll plan the rally-ready getaway—so all you have to do is pack your paddle.
Ready to Serve Up the Best Group Trip Yet?
We’ll handle the planning, booking, and logistics—so all you have to do is show up and play.