Your Next
Chapter
Starts Here.
Elite coaching. Curated destinations. Seamless travel. We combine competitive pickleball instruction with world-class retreats — so you level up your game and your life.
More Than a
Vacation.
To guide players through the next chapter of their pickleball journey by creating an immersive, supportive, and transformational retreat experience where growth is measurable, community is real, and every player leaves with a renewed sense of purpose — both on and off the court.
At Chapter One Travel Services, we believe the world is meant to be experienced, not just seen. By stepping into new destinations, players step into new versions of themselves. They return home not only with improved skills, but with something priceless: a pickleball story worth telling.
To become the premier pickleball retreat experience in the world.
A global community of players who return year after year, each time stepping into a new chapter of their story with greater confidence, deeper connection, and a stronger sense of who they are becoming.
Explore · Elevate · Evolve
Not just a tagline — a journey map. Three words that describe the arc every player travels on a Passport 2 Pickleball retreat.
Step into something new
New destinations. New skills. New parts of yourself. Our retreats invite you to step outside the familiar — physically and emotionally — and discover what's waiting on the other side.
Rise through challenge and support
Elevate your game, your mindset, and your confidence. Our coaching philosophy isn't just about teaching — it's about lifting people up and helping them reach higher than they thought possible.
Leave transformed
You won't leave the same way you arrived. Evolve as a player, as a partner, as a person. This is the promise of growth that sticks — a pickleball story worth telling.
"This is more than a vacation. It's a catalyst for the next chapter of someone's pickleball journey."
Your Season. Your Story.
Every retreat is a chapter in the 2027 Passport 2 Pickleball World Tour — a season-long adventure that takes you from tropical courts to turquoise waters and beyond.
Collect Stamps.
Earn Rewards.
Build Your Legacy.
Every guest receives an official Pickleball Passport at their first tour stop. Each destination earns you a custom stamp — and each stamp puts money back in your pocket.
See the World One Court at a Time
Each stop on the 2027 Passport 2 Pickleball World Tour. Collect your official Pickleball Passport stamp at every destination — each stamp unlocks a $50 credit toward our End-of-Season Championship Tournament.
Sips, serves & Sunshine
7 Days · Club Med Cancún · All-Inclusive
Dinks in Paradise
7 Days · Club Med Turkoise · All-Inclusive
June 2027
Summer Tour Stop
August 2027
Late Summer Tour Stop
October 2027
Fall Tour Stop
Pickleball Travel, Wherever the Game Takes You
Beyond our World Tour, we spotlight the best pickleball events, resorts, and getaways — and plan them with you.
Mar 13
2027
Holland America Line
Private Island Invitational
The first pro pickleball invitational on a private island.
See Featured GetawaysMeet the Team
A world-class travel concierge and a nationally ranked pro coach — together they make every retreat seamless, transformational, and unforgettable.
Robyn Maloy
Owner, Chapter One Travel Services
As an avid pickleball player and dedicated travel concierge, Robyn combines her love for the game with a passion for seamless travel — taking the stress out of planning so you can enjoy the ultimate court-side getaway. Whether it's an official Passport 2 Pickleball retreat or a private pickleball trip for you and your friends, Robyn handles every detail from serve to shore.
Full Bio
David Haynie
Certified Pro Coach & Tournament Competitor
Nationally ranked and certified, David brings tournament-level insight to every session — tailored to where you are and where you want to go.
Full BioReady to Write
Your First Chapter?
Spots are limited and fill fast. Click the yellow box below to fill out our interest form and we'll be in touch with everything you need to secure your spot.
Reserve My Spot