The Coolest Experience You Might Be Missing: Walking With a Caddie

Don't be afraid of a Looper

I played golf for years before I discovered something amazing: regular people—yes, even us—can have a caddie. Not just the pros. And let me tell you, once you walk a course with a great caddie at your side, you’ll never think of the game the same way again.

Sure, I’d had the occasional caddie on golf trips to Ireland and Scotland, and at high-end resorts. But never locally, never regularly. That all changed when I moved to Kiawah Island, South Carolina in 1997.

Around that time, the Kiawah Island Club was just beginning. The Beach Club was built, followed by the stunning Tom Fazio-designed River Course. A few years later, the legendary Tom Watson designed Cassique, and I was thrilled that we were members.

And then it got even better.

Buddy Darby, the visionary behind the club, invited me to join the advisory board (yes, I was the only woman). He’d open each meeting with a grin and a declaration: “This is a benevolent dictatorship. There will be no voting.” That said, Buddy listened, talked things through, and—when he made a decision—it was almost always the right one.

In the fall of 1999, Buddy brought in CaddieMaster, a company that manages professional caddie programs around the world—including some famous private clubs. His concern was that members wouldn’t use caddies, and he wanted the Cassique experience to be truly unique and successful.

The men at the meeting were all for it: let Cassique be a “caddie-only” course. They discussed member costs, club costs, tipping (then $100 a round). Just as the meeting was winding down, I raised my hand.

I pointed out something I knew to be true: women would compare the cost of a caddie to the cost of a cart (caddies were double), and many would pass. And women don’t usually carry cash, so tipping would be a huge obstacle.

The room went silent. But Buddy got it.

Together with Mike Granuzzo and Dan Costello of CaddieMaster, he came up with a brilliant compromise. The cost of the caddie would be just $10 more than a cart fee. And—this was key—they introduced a no tipping policy (except for tournaments). The club and CaddieMaster would split the cost, just to make the program successful.

Dan Costello - Chief Executive Officer

And it was. Hugely.

Eventually, the River Course added the caddie program, too. I was over the moon. Walking with a caddie became my favorite way to play—golf suddenly became more personal, more fun, and more connected.

Fast forward to 2009: The USGA Mid-Am Championship was held at The Kiawah Island Club. The River Course hosted the qualifier; Cassique hosted the championship. Tim Spitz, an unknown and unexpected qualifier, made it through and into the match play. Problem was, he’d only budgeted for a caddie for the qualifying rounds. He shook his caddie’s hand, thanked him, and started planning to carry his own bag.

Cassique Golf Course, Kiawah Island, SC

Enter Dany Clays, CaddieMaster’s on-course manager. Dany told Tim that his caddie was on them—the cost was covered. They wished him luck.

Dany Clays - Vice President Operations

Tim won. And then he won again. All the way to the final match, where he faced off with the reigning champ, Nathan Smith. Tim lost when Smith chipped in for the win, but Tim’s entire family—who had driven 24 hours in a rented van to see him—was there to cheer. The whole crowd roared for him. The Cinderella story. The CaddieMaster Cinderella Man.

What a gesture by CaddieMaster. What a memory. And yes, I still tell the story—even if Tim doesn’t.

Since then, I’ve stayed in touch with Dany and Dan. In 2021, CaddieMaster began supporting a program at The Cliffs Communities, and I’ve loved every opportunity to walk with one of their exceptional caddies.

There’s nothing quite like it—walking the course with someone who knows the land, reads the greens, and becomes a teammate. You build a bond not only with the caddie, but with your playing partners too. You focus more. You laugh more. You remember more.

So if you’ve never tried it—maybe because you were intimidated, or thought it was only for the pros—please, do it. It’s one of the most authentic, joyful, and unexpectedly cool experiences in golf.

Have a caddie story of your own? I’d love to hear it.