A Tradition Like Many Others

The Secret to Planning a Buddy’s Golf Trip

By Miles FisherMarch 16, 2021

I can’t recall the last time I truly “caught up” with friends. Coordinating a non-business related call or zoom can feel depressingly futile, often resulting in a two dimensional hi —smalltalk— bye on a Saturday morning. That’s golf time, anyway. 

More than ever, I long for a buddy’s golf trip (BGT). I dream of three days with a bunch of old friends and a few new ones in a part of the country I seldom get to for good golf, great BS, and little else. Throw in some decent food, passable wi-fi in the room and poor phone reception everywhere else and I’m in heaven. 

I fell in love with this game thanks to a golf trip with friends. Actually, it was my older brother’s annual boondoggle —The Whiskey Flask Matches (official motto: “A Tradition Like Many Others”)— that introduced me to my favorite means of “catching up” with friends.

Each year, a handful of guys would venture somewhere new (think places like Brandon Dunes, The Broadmoor, Greenbrier, Sea Island, Sand Valley, Big Cedar Lodge) and get in three days of mini Ryder Cup team action. When a spot opened up due to a last minute cancelation, I was called off the bench to fill it.

As my brother noted when my invitation came; “Listen, there are very few times where we do something truly important.  This weekend will not be one of those times.” And yet my first Buddy’s Golf Trip would impress upon me a new dimension of the game. It was a lot of golf with 2 rounds on foot each day, but I found it exhaustingly invigorating. 

I came to discover that a buddy’s golf trip, when done right, can provide an immeasurable social return on investment over the next… rest of my life. Finally, a civilized means of staying “caught up” with some of the most cherished people in my life. What a useful vehicle this trip could be!

Since my first Flask, I’ve been on a number of these adventures of varying scale. I’ve organized a handful of them myself and learned that if you’re able to lock in a solid group of friends, it’s a hard thing to screw up. These are strange days, so it could be a big production or something more financially friendly. The important part is good people coming together and to get away. 

It's key to get the first annual trip right. Once a precedent is set, all you need to do is have fun and keep the train on the tracks. But how to nail the inaugural trip? Here are some of my personal tips that you can use to create your own “tradition like many others.”

The main lodge at Sand Valley looking inviting.


The effectiveness of an original logo and the ability to produce a clean and simple PDF can not be understated. Before a list of invites is even drafted, you’d do well to give your gathering what those in marketing call “brand identity.”

This need not be complex and time intensive. Even the simplest concept, when properly executed, can help foster a sense of ownership over this new institution much in the same way membership to a private club heightens our sense of occasion and custom. 

Once you have a trip name and a little logo, it’s time to get cracking on your PDF. I’m sure your friends are willing to travel for a great weekend, but you’re gonna need to sell ‘em a little bit. 

Let’s breakdown a personal example from one of my own buddy’s golf trip — The Pilgrimage. The first ever Pilgrimage was held in Wisconsin at Sand Valley and it was a success in every possible way. This past year’s Pilgrimage to Pinehurst was postponed due to COVID, but the details here are all real. 

The Pilgrimage needed a strong logo to give the trip a bigger presence than a one-off trip. I knew I wanted something that incorporated a sense of travel (and in so doing, salvation) and begun looking for old depictions of religious pilgrims. I found an old wood block carving of an ancient hiker with what appears to be a gourd strapped to his back and some very choice headgear. Perfect! I scanned it, replaced his walking stick with a 6 iron, and bingo — we now have  our handsome hero / logo / icon.

The Pilgrimage logo.

With our Pilgrim now identified, the pieces are beginng to fall into place. This is getting real. Next up, book your reservations.


While there’s good golf to be had all around the world, some places (like Sand Valley and Pinehurst) are more accommodating to the BGT than most. Ideally, you’re looking at a place that is fully contained on the premises with solid accommodations, a few good dining options, and ideally three distinct courses or more (par 3’s count, extra points for jumbo putting courses). 

I’ve learned that places like these often employ the most lovely people working in their reservations department. Pick up the phone and plan on a good hour getting super friendly with whomever is going to help you make your plans. In my case, Michelle became my new friend at Pinehurst the moment she first answered the phone, and let me tell you, she deserves six out of five stars. 

I began by simply asking for her help. I told her we were 12 guys. We wanted to arrive on a Friday afternoon and check out late Sunday morning. We’re looking to book a weekend anytime 4 - 6 months out. I explained we were keen on 6 double rooms and ideally a group package that gives us as many rounds and food credit as we can get. We’d also be grateful for help booking 3 tee times for 3 different rounds and help making restaurant reservations. 

Michelle helped me do all of that in the first 20 minutes. Once the essentials were pinned down, she started waving her magic wand. She told me that we could have live music one night if I texted her friend the guitarist. She offered us our own private common room during the entire stay to use as our home base if we wanted. She gave me her mobile number if I had any small requests to text. 

Michelle emailed those potential add-on options and pricing along with photos of the rooms we’d stay in. Most importantly, she quoted me the deposit I’d need due by the end of the week and what the cancelation policy was. 

Okay, reservations made. Logo has been designed. You’re cooking with gas now, and so far, have put no money down yet. 

Now it’s time to get cracking on the pitch to your friends in the form of a PDF. This is an important piece of the puzzle. And here’s why: do you actually read any emails that are longer than 3 sentences? Do you respond to text messages that are paragraphs long? I tune out when that happens. 

But if a friend emails or texts me something as simple as this; “Hey - this is happening, see attached. I need a yes or no by the end of the week. Hope you can make it - gonna be epic.” Now we’re talking. Let's be honest, you've given them something concrete that they can share with their significant other to get the necessary permission that's required for such activities. The PDF helps them get the approvals they need to book a flight and block off those days in the calendar.

The BGT Iteneary PDF will be the one go-to source that has the full schedule, specific photos of the experience, reliable outline of expenses and an overview of what to expect. Sprinkle that with some mouth watering imagery that you cribbed from the resort’s website and you now have all your marketing and logistics in one place. Here's an example for our postponed trip from 2020. 

I took the deposit amount that my new pal Michelle quoted for me, divided it by 12 (number of attendees), and then asked each guy to Venmo me that amount to lock in our group reservation. “Yes, of course it’s refundable…” And given what we're getting, the costs are reasonable and transparent. 

Now, with my buddies all paid up, I can call back Michelle and make it official. This is where the fun starts and you now have several months to build up excitement. One of the best ways to do that is by making a custom apparel using your newfound “brand assets.” Go nuts. Afterall, what's worth doing is worth doing with exclusive merch. 

Logistially these types of trips can be a big lift for the organizer, but by putting thought into details you can ensure your closest friends have the best weekend of the year. What could be better than that?

Here’s hoping 2021 ushers in your own “tradition like many others.”