Featured Pickleball Getaways
Handpicked events, resorts, and itineraries for players who love to travel. Your next story might start here.
Featured Right Now
Now BookingFeatured Event
Private Island Invitational with Holland America Line
Half Moon Cay · March 13, 2027 · Eastern Caribbean
Holland America Line is hosting the first professional pickleball invitational on a private island — RelaxAway, Half Moon Cay — on March 13, 2027. The event takes place during a seven-day Eastern Caribbean cruise aboard Nieuw Statendam (San Juan & St. Thomas), organized with the PPA Tour and Major League Pickleball.
Countdown Cruises
Four Countdown Cruises lead up to the main event, featuring PPA player appearances, coffee chats with the pros, pickleball trivia, onboard lessons, and island play.
- Nov 20, 2026 — Southern Caribbean — Nieuw Amsterdam
- Dec 12, 2026 — Western Caribbean — Zuiderdam
- Jan 2, 2027 — Eastern Caribbean — Eurodam
- Jan 23, 2027 — Eastern Caribbean — Eurodam
What Makes This Trip Unique
- First-ever pro pickleball invitational on a private island
- Seven-day Eastern Caribbean cruise aboard Nieuw Statendam
- PPA Tour & Major League Pickleball organized event
- Pro player appearances, coffee chats & onboard clinics
- Island play at RelaxAway, Half Moon Cay
- Stops in San Juan & St. Thomas
Who It's For
Players, couples, and friend groups who want to witness history — the first professional pickleball invitational on a private island — while cruising the Eastern Caribbean in style.
Player lineups to be announced
Contact us for current pricing and availability. Spots are limited — don't miss your chance to be part of pickleball history.
Now BookingPineapple Beach Club Antigua
Long Bay, Antigua · Adults-Only All-Inclusive
Six dedicated outdoor pickleball courts on a gorgeous quarter-mile crescent of white sand. Morning rallies, afternoon swims, evening rum punches — the perfect active-lifestyle escape.
- 6 dedicated hard-surface courts with permanent nets
- Unlimited meals, drinks & non-motorized water sports
- Court reservations & equipment provided on-site
Featured ItineraryCosta Rica: A Pura Vida Chapter
10 Days · 9 Nights · Guanacaste → Arenal → Central Valley
Three iconic regions, three distinct stays — pickleball at every stop. From the Pacific coast to volcano country to a private mountaintop estate.
- Chapter One: Four Seasons Papagayo — 6 dedicated courts, Pacific coast
- Chapter Two: Tilajari Resort, Arenal — volcano hikes & hot springs
- Chapter Three: Bella Vista Private Resort — mountaintop courts, sleeps 28
Why Plan It With Robyn
Pickleball-First Planning
We build your trip around the game you love — courts, clinics, and play time come first.
Time Back in Your Hands
We handle the details so you can focus on what matters: showing up and playing your best.
Someone in Your Corner
If plans change, we're one call away. You're never navigating travel surprises alone.