From a Crazy Idea to 40 Pickleballers in Paradise: Our St. Lucia Retreat Recap
- ccaatravel
- 3 days ago
- 5 min read
I just got back from St. Lucia, and I'm still pinching myself.
Over 40 people. A private beach dinner. Five days of pickleball in paradise. New friendships that looked like they'd been years in the making. And me, sitting in a clubhouse overlooking the courts, watching a dream I'd had less than a year ago come completely to life.
Let me back up.
It Started With a Training Call
Earlier in 2025, I was at a training with one of my travel suppliers. They were walking us through everything they offer for group travel — the perks, the amenities, the extras — and they said something that stuck with me: think outside the box when it comes to groups. Anything people have in common can be a group.
That's when it hit me. Pickleball.
I've been playing for three years, and if you haven't discovered it yet — fair warning — it is the most addicting game you will ever play. I'm somewhere around a 2.5 to 3.0 rating, so I'm no pro, but I am completely hooked. And I'm not alone. Pickleball is the fastest growing sport in America, and the community around it is unlike anything I've ever seen.
The wheels started turning, and I set my goal: I was going to plan a pickleball retreat. Not just anywhere — I wanted to do this right.
Why Sandals Was the Only Choice
After a lot of research and many phone calls with my suppliers, the answer became clear: Sandals. The premium all-inclusive brand of the Caribbean recently partnered with USA Pickleball, upgrading their resorts to include certified pickleball courts. Some properties have as many as 12 courts. They take the sport seriously — and so did I.
Sandals Regency La Toc in St. Lucia became our home base. Beautiful, luxurious, and ready for a group of pickleballers who meant business.
Finding the Perfect Partner
Next came finding a pickleball instructor willing to share my vision. A fellow travel advisor connected me with a friend of hers from Cleveland, and after a two-and-a-half hour phone call about what I wanted to create, we both knew we were the perfect pair.
I threw myself into promoting the retreat — posting across Facebook, joining pickleball communities, connecting with fellow players everywhere I could. Then it happened. A couple from Texas reached out. They wanted in.
Within three months, every room was sold out. We had a waitlist.
The Retreat That Delivered Everything — and More
With this being our very first retreat, I made the decision to come along and be on the ground to make sure everything went perfectly. And let me tell you — Sandals' groups department is absolutely phenomenal. Every single detail was planned and executed beautifully.
We kicked off the week with a private welcome dinner on the beach. The food was spectacular, the sunset was stunning, and one by one our pickleballers arrived — strangers to each other, but not for long. I had some fun mixers planned to break the ice, and by the time we introduced our instructor, the energy in that group was electric.
Every morning, Sandals gave us exclusive court time. Our instructor had mapped out a smart strategy — working with everyone individually while also matching players up by skill level so every session felt both challenging and fun. I sat in the clubhouse that first morning, overlooking the courts below, and I felt it wash over me.
My dream had come true. I did it.
But I need to take a moment to talk about the Sandals team on those courts — because they deserve every bit of praise I can give them. From the very first session, they showed up and showed out. A huge cooler full of fresh juice and iced water was waiting for us courtside. Cold towels appeared out of nowhere and were delivered directly to players mid-game to keep everyone cool in the Caribbean heat. Up in the clubhouse, there were sandwiches, fruit, coffee, and water — a full spread, ready and waiting. Fun music was pumping the whole time, keeping the energy high.
And then it rained. For a moment I held my breath — but before I could even think about what to do, the Sandals team was already out there with rollers and a leaf blower, drying off the courts so we could get back to playing as quickly as possible. They had thought of absolutely everything.
My favorite moment? Darian — one of the Sandals team members who I absolutely adored — going around the courts with a cooling mist sprayer, spritzing players in the face and draping cold towels around their necks with the biggest smile on his face. Our group was being pampered to the tenth degree, and honestly? There was no way I could have topped what Sandals delivered that day. I didn't have to. They took care of my people, and that meant everything.
But here's what I didn't expect: how much I was going to fall in love with these people. Some of the nicest, funniest, most genuine humans I have ever had the pleasure of spending a week with. Five days of play, skill-building sessions, and a tournament to close things out — and through it all, something magical happened. People who had never met before became friends. Real ones.
And then there was the night we decided to mix things up entirely. Starting at 6pm, we took to the courts for an evening session under the lights — and it was an absolute blast. The sun had set, taking most of the Caribbean heat with it, the music was going, and those lights? They were incredible. Bright, clear, and perfect for play. There's something about pickleball under the lights at a Sandals resort in St. Lucia that just feels a little magical. It quickly became one of everyone's favorite memories from the whole week — and honestly, mine too.
Toward the end of the retreat, Sandals hosted a private cocktail party for our group. I stood back and watched everyone laughing and mingling like they'd known each other for years. It was one of those moments you file away and keep forever.
What's Next — Because This Is Just the Beginning
The response from that retreat was more than I could have hoped for. Certified pickleball instructors reached out wanting to partner with me, and I'm thrilled to announce that two more retreats are already on the books for 2027.
March 2027 — Sandals South Coast, Jamaica. This resort is currently undergoing a major transformation and will only be open for four months before our group arrives. Our pickleballers will be among the first to experience Sandals 2.0, and I cannot wait.
October 2027 — Sandals Curaçao. Another stunning destination, another week of great play, great people, and everything Sandals does best.
If you love pickleball — this is your sign. Come join us. Spend a week in the Caribbean, meet incredible people, improve your game, and make memories that will last long after the tan fades.
You will not regret it. I promise you that.
Ready to claim your spot? Registration is opening soon - so keep an eye out on my website
Courtney is a family vacation planning specialist and Elite Agent with MainStreet Travel Agency. She specializes in Disney, Universal, all-inclusive resorts, cruises, and group travel — including her signature pickleball retreats.
📧 CCAATravel@gmail.com · 📞 740-507-0262
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