The Big Group Trip

A great golf trip can be organized chaos. One year, I went with a group of forty guys to Las Vegas for a golf trip that included Coyote Springs, Paiute, Reflection Bay, Dragon Ridge, and Reunion. Multiple buses were rented fully stocked with beer and snacks, we played for daily and overall prizes, and I watched plenty of money change hands—none of it ending up with me. Trips like that have a life of their own. The golf matters, of course, but what you really remember is the bus rides, laughter, the stories told after dinner, and the way a large group somehow settles into its own rhythm by the second day.

A Trip with Laurie

Not all great golf trips are loud or complicated. Some of the best are simple, easy, and shared with the right person. One of my favorites was a quick trip with my wife, Laurie, to the Food & Wine Festival at Casa de Campo in the Dominican Republic.

Each day had the same nearly perfect rhythm: a morning round of golf with interesting people from around the world, drinks at the swim-up bar in the afternoon, a short nap, and then an evening of wonderful food and wine pairings. It felt effortless in the best possible way.

We had the same caddie, Bartolo, for all three rounds. By about the third hole of the first day, he understood both of our games. After a good shot, he would shout,

      “Buena bolla, Mr. George,”

and before long he felt like part of the trip rather than just part of the round.

On our final day, we were paired with Claudie and Vivian, a wonderful couple from Atlanta that we still keep in touch with. Laurie’s putter caught fire that day. She trusted every line Bartolo gave her, and the putts started dropping from everywhere. After she made another twenty-footer on the 13th hole, Bartolo looked at me and said,

     “Oh, you in big trouble today, Mr. George.”

He was absolutely right. Laurie cleaned my clock, and afterward, with Claudie and Vivian there to witness it, I toasted her with the drink she had won and gave the required line:

     “Thank you for kicking my butt today.”

Traveling Alone

Sometimes it’s nice to go on a golf trip alone and just let the world come to you.

No schedules to coordinate. No debates about where to play or where to eat. Just a few tee times, a tank of gas, and the quiet confidence that the game—and the people around it—will take care of the rest.

One mid-October, I took a short solo trip that started near Baltimore and looped through West Virginia and Delaware. Nothing fancy—just a handful of tee times booked through GolfNow and a willingness to see how the days unfolded. The itinerary included Waverly Woods Golf Club, Oglebay Resort, and Frog Hollow Golf Club—three very different stops, each with its own personality.

At Waverly Woods, I was paired with two friends, both five handicaps—right in my wheelhouse. Those are the rounds that settle in quickly. Good rhythm, easy conversation, a shared appreciation for the course and the nuances of the game. By the back nine, it felt less like a pairing and more like a regular group.

From there, it was a short drive to Oglebay, where I found myself with two brothers-in-law from Pennsylvania, on a trip of their own with their spouses. The weather turned on us that day—cold, wet, and just uncomfortable enough to be memorable. At one point, we even had snow falling on a few holes. The kind of round where you stop worrying about your score somewhere around the sixth hole and just lean into the experience. We laughed our way through it, which is usually the right play.

Then came Delaware—and Frog Hollow.

This time, I was paired with three twenty-something beginners. None of us had ever met; all four of us had booked as singles. It was a beautiful day, the kind that makes you want to play forever… which, as it turned out, we nearly did.

After about four holes, I made a strategic decision: I was done helping look for golf balls. Between the stickers and the weeds, my pants were taking a beating, and the odds weren’t improving. The round stretched on, as these things do, but there was something endearing about it too. Each of them managed to make a par during the day—small victories that felt like big ones. Scores may have drifted into the 120s, but they left with something to build on, which is really what the game is about early on.

After the round, they headed home, and I wandered into the bar for lunch—no plans, no expectations.

And that’s when the trip delivered its final surprise.

At the bar, I struck up a conversation with a group of regulars who were getting ready to head out for their afternoon nine-hole skins game. One of them casually mentioned he held the course record—63. That got my attention.

They asked if I wanted to join.

Why not?

We headed back out, and just like that, I went from solo traveler to part of the group. I rolled in a couple of putts, caught a few breaks, and somehow managed to double my money. Not a bad afternoon’s work.

We finished up, went back into the bar, and settled into one of those easy, wide-ranging conversations that only seem to happen around golf—about the course, the area, and the places we’d all traveled to play.