The Heart Behind Picklebilly Travel

Five years ago, I was retired when someone approached me to curate a pickleball trip.

I said yes.
I gathered a group of friends.

And honestly… it wasn’t very good.

We stayed in tiny cabins that felt like they were designed for kids. Some people were sharing tight spaces. The food wasn’t enough for a group playing hours of pickleball every day—we actually had to ask for more. It just missed the mark in a lot of ways.

And here’s the surprising part…

I still remember that trip with a full heart.

Because what did work had nothing to do with the cabins or the meals.

It was the moments.

Singing together on the bus.
Taking tequila shots.
Sliding into the water and laughing like kids.
Sitting together and talking—really talking.

That’s what stayed.

That trip taught me something I’ve never forgotten:

The magic isn’t in the logistics. It’s in the connection.

Now, fast forward to today.

Our recent trips look very different on the surface.

Private suites.
Beautiful villas.
A private chef.
Thoughtful coaching and curated experiences.

All of that matters. It elevates the experience.

But it’s still not the heart of it.

The heart is what happens in between.

The teasing after a great rally.
The laughter in the pool after a long day of play.
The shared rides to dinner, to the beach, to explore somewhere new.
The quiet moments—like sitting together, or even meditating side by side.

That’s the part I care about most.

That’s the part I’m always chasing.

And I say “chasing” because you can’t force it. You can only create the space for it… and then let it happen.

But somehow—it always does.

At the end of every trip, people ask the same question:

“Where are we going next?”

Not because of the villa.
Not because of the itinerary.

Because of how they felt.

We’re living in a time where it’s easy to feel disconnected.
We’re on our phones. We’re busy. We’re pulled in a hundred directions.

But people are hungry for real connection.

And when you put the right group together in the right environment… something special happens.

That’s what Picklebilly Travel is really about.

Not just where we go.

But how we feel when we’re there—together.

Janice Mundee