Editor's Note: In 2019, I was invited to go on a golf trip with one guy I knew a little bit and seven that I didn't know at all. Turns out, travel golf is the best recipe for making new friends. That trip was the second installation of what would become a franchise for the organizer, my pal, Miles Fisher. It proved that getting people together—be it on an adventure organized by the pros at The Fliers Club or just a homespun outing— is the most important thing.
A few years after my first trip with his crew, Miles wrote about golf trips for me on a site that has since sunsetted. Every year, people DM and ask how they can find the link, so we decided to update it here on The Old Ghosts. A buddy's golf trip is the most important unimportant thing in our lives, so why not make it the best it can be?
I am writing this somewhere over the Atlantic, en route to Scotland for a few days of golf. There are worse places to think about friendship.
Adult friendship rarely disappears dramatically. It thins. It becomes a text thread, a "let's find a weekend," a birthday note written three days late. Nobody means for it to happen, but years move quickly. Before you know it, the people who once occupied whole seasons of your life become names that light up your phone.
Golf, for all its absurdity and occasional cruelty, remains one of the best excuses ever invented to interrupt that drift. Especially golf trips.
You need tee times. You need pairings. You need a reason to be in the same place at the same time for longer than a meal. One conversation happens over the first six holes. Another begins on the walk to lunch. A third comes late at night, when everyone is tired enough to stop performing. The game gives friendship space and time without making it sentimental.
I fell in love with this version of golf through my older brother's annual boondoggle, The Whiskey Flask Matches, whose official motto remains unimprovable: "A Tradition Like Many Others."
Each year, a handful of guys would travel somewhere new for three days of mini Ryder Cup team action. Pinehurst. Bandon Dunes. The Broadmoor. Greenbrier. Sea Island. Sand Valley. Big Cedar Lodge. When a spot opened at the last minute, I was called off the bench.
As my brother put it: "Listen, there are very few times where we do something truly important. This weekend will not be one of those times."
He was right, of course. He was also not entirely right.
That first trip taught me that a well-made golf weekend could keep certain friendships current for years.
Since then, I have organized a number of these trips myself. Some polished. Others held together by weather, Venmo, and blind optimism. The lesson is simple: lock in the right group and it is hard to ruin.
The important part is not luxury. It is not the merch. It is not even the golf course, though a great course certainly helps.
The important part is the planning.
The best trips create just enough structure for everyone to relax inside it. Too little planning and the organizer spends the weekend solving problems. Too much and the thing begins to feel like a corporate retreat with handicaps. Get the first trip right and you have a chance to create something people will protect (and spouses will not begrudge on an annual basis).
Give the occasion a name. A name changes the weight of the invitation. It tells people this is not merely "a few of us maybe playing golf somewhere if schedules permit." It is a thing, a small institution. Make it slightly funny, slightly sincere, easy to imagine on a hat.
For one of my own trips, I created something called The Pilgrimage. I found an old woodblock image of a religious pilgrim — gourd strapped to his back, very serious 15th-century Spanish headgear — and replaced his walking stick with a 6-iron. Suddenly, we had our handsome little patron saint and the whole thing felt real. A name and an icon. That was enough.

Make the invitation easy to accept. Nobody wants to read a long email about logistics. A clean PDF does the work: dates, place, schedule, cost, photos, when you need an answer. Something concrete your friends can share at home. The message itself can be almost comically short: "Hey, this is happening. Details attached. I need a yes or no by next Friday." That is not laziness. That is hospitality. See example from 2020 (note: made before GPT—now it’s orders of magnitude easier).
Pick a place that can handle the whole weekend. Self-contained: strong lodging, multiple courses, easy food, a good bar, somewhere informal to gather. Sand Valley understands this. Pinehurst does too. Bandon understands it almost spiritually. Scotland and Ireland, in their ancient and weather-beaten way, may understand it best of all. The magic is not only the architecture of the golf, but the architecture of the day. Breakfast. First tee. Lunch. Second game. Shower. Drinks. Dinner. A walk back in the dark. Some stupid argument about a conceded putt. Sleep. Repeat.
When planning, pick up the phone. For The Pilgrimage to Pinehurst, I spoke with a woman named Michelle in reservations who, within twenty minutes, had solved the basics and then started waving the wand. A private room for the weekend. Thoughts on dinner. Her friend the guitarist, is available one evening if I texted. Details like that are the difference between booking a trip and hosting one.
Be clear about money. Tell people what the weekend costs, what is included, and when payment is due. Divide the deposit by the number of guys, send the Venmo request, and move on. A well-run trip feels generous even when everyone is paying his share. Everyone is in charge of their flight in and out. You handle the rest and split the bill afterwards
Leave room for the trip to become itself. You need tee times, meals, rooms, and a basic format. You do not need to choreograph every hour. The moments people remember happen in the gaps (the bad match that turns oddly competitive, the quiet drink with the friend you have not really spoken to in two years, the private joke that becomes permanent…). The soul of the thing comes from repetition: the same toast, the same complaint, the same person being late, the same phrase that makes no sense to anyone outside the group. That is how a weekend becomes a tradition.


A scene from the first tee at The Pilgrimage in Sand Valley. On the right, it's good to have friends who believe in large format.
I’m a little older than I was when I first wrote about this. Old enough to know that friendship requires more protection to keep vibrant through the years. The people I still see become the people I still know. The people I do not see become “let’s find a time” friends.
A golf trip is one small way to resist that.
A few days with old friends, walking through weather, trying to hit a small white ball toward an ancient target.
I am on my way to Scotland now, so I am probably over-romanticizing the enterprise. Fine. Golf invites a certain amount of over-romance. The wind. The old hotels. The first-tee nerves. The sense that the course was there long before you arrived and will be there long after you leave.
Call it a boondoggle. Call it The Pilgrimage. Call it whatever you want. Just give it a name, pick a place, send the invitation, and go.
Miles Fisher writes Fisher's Island on Substack.