The Anatomy of the Great 3-Day Golf Buddy Trip

I’ve had the distinct pleasure of planning now 10 consecutive annual golf buddy trips with a great group of college fraternity buddies and their adjacent friends.  I’ve learned from some mistakes and have put together a road map for what I consider one of my true legacies in life:  I get to bring a group of 8-12 guys together once a year for an event that they look forward to more than anything else.  A few simple rules before we get started:

Rule #1:  Remember that as the Golf Buddy Trip Captain, it’s fair to expect that you love the game of golf as much, if not more than anyone else that goes on the trip with you.  No matter how great the golf courses are or how well or poorly you play, the most important thing is the company you keep and if the boys have fun.

Rule #2:  With Rule #1 in mind, you can’t make everyone happy.  Guys will moan and groan about location, the lodging, the format of the competitions, or who they are playing with.  I’ve become much more of a “Golf Trip Dictator” than in years past, partly because my reputation in buddy trip architecture precedes itself and I’ve found that providing a finite number of options is best. If guys don’t like the location, the courses, or who they are paired with, then they don’t have to come.

Planning the First Trip

I tried for years to get a trip together right after several of my Fraternity brothers and I finished college.  I found that guys were too focused on their careers or still caught up in the college life and weren’t playing golf.  In some respects, being apart made the golf trip hearts grow fonder, and eventually when we didn’t see each other as much for a few years, the itch for the golf trip became a reality. It took a few years until the group was finally “ready.”  Don’t force it.

For our first trip, I did my best to focus on a geographical area (about 3-4 hours from everyone) and that was moderately priced.  With most of us between 24-27 years old at the time, most of us didn’t have much extra change for an expensive, luxurious golf trip. If the guys have spouses or kiddos, it’s good to keep the trip fairly short and then always grow longer as time goes on. We selected Geneva National in southern Wisconsin and stayed at another cheap resort nearby to cut down on costs.  We had a blast.  We got our starter to act like he was removing one of our players because he wore salmon colored shorts.  We slept in lofted hotel rooms with legit bunk beds.  One of the guys bought two green jackets with golf ball embroidery from a thrift store for the winners. It was a perfect start.

There’s no perfect formula for the first buddy trip, or even any of them thereafter, but here are a few recommendations:

Location:  For the first trip, I recommend identifying a resort within a 3-4-hour drive from all golfers.  You don’t want them to feel the burden of taking a whole weekend away from a spouse or significant other, kids, or their job by being in a car the whole time.  Resorts that have 3 or 4 courses on-site instead of being road warriors between courses tend to work best.  I also recommend making sure that you choose a resort or location that has a restaurant(s) on-site so you aren’t having to drive anywhere.

Team Competitions:  We originally tried to do best-ball team competitions with handicapped aggregate scoring and it was a nightmare.  First, guys who don’t play all that often have no concept of an actual handicap.  I had guys saying they were 20 handicaps and proceeded to shoot in the 120’s.  It skewed all the scoring and was a huge challenge adding everything up at the end. We eventually went to a pure best-ball match play format and it was one of the best decisions we made during the 10 years of the trip.  I don’t recommend Alternate Shot or some type of unique competition format.  Most guys want to play their own balls anyways and the more complicated the format, the less likely people will buy into it.  Lastly, don’t feel compelled to play for money unless it fits your group.  We always talk a big game, but eventually when it came time to pay up, we all just shuffled the money together and bought more beer.

Make it Fun:  Don’t get so caught up in the rules of golf or etiquette.  If guys wanted to be bossed around and told what they are doing wrong on the golf course, they would have just saved the money and stayed home with their significant other or their parents.

Recipes for Golf Buddy Trip Success

I have found that there is a bit of a “special sauce” when it comes to golf trip itinerary construction.  I tend to structure things based on a “theme” for the day.

DAY ONE:  CHRISTMAS EVE

One of my buddies used to always joke that I treated the first day of our golf or other buddy trips like it was Christmas Eve.  I drank too much and then felt like garbage the rest of the trip.  I was always too excited and wanted to kick everything off with a bang, only then to wake up on Christmas morning the next day and realize there is no Santa Clause.

I view the first day of the Golf Buddy Trip is a similar light, but I’ve managed against the Christmas morning hangover in a few ways.

• Plan to play a course that is typically great, but the least difficult of all the courses. If the course is unavoidably difficult, plan to play the less demanding tees to ease the pain, particularly for those who don’t play too much golf.  You don’t want fringe golfers in your group to have a terrible first round and then regret they came in the first place.  Of course, you can’t completely avoid this, but usually a good round for most players sets a great tone for the rest of the weekend.
• I typically plan the first round around the first available twilight tee times for several reasons. First, you get a better rate and you can brag to everyone the great deal you got them on a fantastic golf course.  More importantly, usually the course is pretty empty at these times and pace of play is better.  Lastly, most courses don’t send out cart girl staff after a certain time and you can prevent those that like their cocktails from being over served on the golf course the first night.
• Don’t plan a big event or excursion away from the resort the first night. I made the mistake on our second trip of taking the guys out to the casino near Grand Traverse Resort in Michigan.  Most of us didn’t get home until 3 am in the morning and were blowing chunks on the first tee at The Bear, only the most difficult course we’ve probably ever played.  The excursions can wait until the next day.

DAY TWO:  THE MARATHON

I call the second day the Marathon for two direct reasons:  It’s the day we play the most golf and drink the most beer.  Period.  These are usually the days that people vaguely remember but have the best memories and stories.  Our Marathon Day stories include me asking the rest of my foursome to be in my wedding party, purchasing all the Bud Lights from the cart girl by 8am, and having to locate a rogue golfer in our group who took one of the carts on an excursion into a pond.  And that was all the same trip.  On the same day.

A few tips for Marathon Day:

• You should never plan a Marathon Day away from the resort that you are staying. There should be no one driving a car, taking an uber, etc.  When planning trips that don’t have 3-4 courses on-site at one location, I always have Marathon Day at the 36-hole facility that is our “home base”.  A great example of this was Lawsonia in Green Lake, WI. We started our trip at SentryWorld and finished at Erin Hills, which are two of the best courses in the state, but our trip was centered around the two courses that had enough lodging to hold all of us together without breaking the bank.  We played 45 amazing holes at one of the true hidden gems in the Midwest.
• Schedule the tee times early enough in the morning to make sure you have enough time for an additional wrap-around nine holes if possible. Typically, we’ll do a scramble or switch up teams for a lighter final 9 holes. And we’re usually pretty intoxicated and don’t really care about the competitions anymore as it is.  Having the tee times early enough also potentially prevents some of the guys from having too much fun on Christmas Eve.
• Plan a dinner with everyone together at the lodge or restaurant at the resort. It’s always a blast and important to make sure some of the guys actually eat.  We all need a base of food to soak up the alcohol we just consumed for 12 straight hours.

DAY THREE:  FLAGSHIP DAY

I typically schedule what is considered the best regulation course last of our 4-rounds on what I call Flagship Day.  I like for the trip to build momentum.  The first day is for having fun and reconnecting with guys that you haven’t seen in a while.  The second day is about playing as much golf as humanly possible and getting buzzed (or ham-boned drunk) in the process.  Day three is about playing a damn good golf course and then telling stories about how awesome it was later that evening.  My Flagship Day best practices:

• I typically schedule the Flagship course to be off-site and a little later of a tee time. Usually these courses are off the beaten path and require a little commute.  Also, doesn’t hurt to give the guys some extra sleep considering the Marathon from the day before.
• In recent years, we’ve changed the format to Individual Match Play like Singles on the final day of the Ryder Cup. Guys tend to like it.  Jury is still out if it will become an annual staple.
• I recommend getting caddies if it’s a walking only course. We did so at Erin Hills and I can’t imagine I would have finished had I not had someone carrying my bag.  Damn you Fireball from the Marathon Day before!
• To engage the fringe golfers, I often didn’t play a second 18-holes after our Flagship round. We either plan a non-golf excursion (a boat trip, casino visit) or took advantage of a Par 3 course on-site.  Some of my favorite memories on a golf course were at Threetops at Treetops Resort in Michigan.  I’ve found it helps to avoid “golf burnout” for the longer trips.  If you’re planning a 2-night, 4 round trip, then you may not have this luxury.

BUDDY TRIP DO’S & DON’TS

• DO take recommendations or referrals from your buddies to add to the group. Some of the best additions to the group are people who were on the peripheral of my network and I am now longtime friends with.  It’s amazing to think that we’ve had 23 different guys at some point attend a trip.
• DON’T make anyone sleep on a sleeper-sofa. I made this mistake a few times in the early years to cut down on costs but the griping about it (rightfully so), wasn’t worth saving the extra $20/guy.  For those that are more mature in their careers or spending abilities, I’d even recommend lodging that doesn’t force guys to share rooms.  We’ve gone from bunk beds and sleeper softs to beautiful homes such as the one we stayed on-site at RTJ Oxmoor Valley in Alabama.
• DO make sure that if you are staying at a lodge or regular hotel that you double check that the rooms have refrigerators in room. I didn’t do this one year when staying at Tullymore & St. Ives.  Fortunately, several of our guys brought coolers, but otherwise it would have been a buddy trip disaster I may have never recovered from.  Side note:  Bring coolers anyways.
• DON’T make scheduling dining away from the golf resort a big priority. We’ve tried to do this several times and we either never made it or guys just wanted to eat pizzas back at the room.  Your group may be more inclined to venture out for a hidden gem or dive bar near the resort, it just hasn’t been our style.
• DO schedule one group dinner at the resort in a private room if possible. It may cost an extra $10-$20/golfer but it’s well worth it to make sure that 1) you have enough seating for everyone to eat together and 2) you can avoid being disruptive to others if you start to get a little rowdy.
• DON’T over-engineer the golf competition pairings. It’s nearly impossible to avoid guys playing with someone multiple times and the groupings are never going to be 100% fair.  I’ve found that guys tend to manipulate the groupings a little as they realize they haven’t played with someone.  At first this really bothered me but ultimately I realized they had more fun when they felt they a little say in the pairings.
• DO have great prizes for the winners of the event or any games such as Closest to the Pin or Longest Drive. I’ll never forget the first time I saw that Masters-like Green Jacket!
• DON’T make the weekend about money. I have found the best way to do this is to pinpoint one person (usually I elect myself to get the reward points) to incur all the main dining or group lodging charges and then everyone can equally Venmo or PayPal back a few days after.
• DO make tipping the cart girls, restaurant staff, and hotel cleaning staff (if applicable) a BIG priority. These folks are working hard to make our one weekend getaway a year to be memorable. Don’t be a cheapskate.
• DON’T give the guys too many options when planning the location and dates for the trip. I’ve made the mistake of giving like 6-7 options of locations or date configurations and the group couldn’t agree on anything. Give two date options and 3 different locales to pick from. Take a vote with a Google Form or a darn Survey Monkey if you have to. Worst comes to worst, pick the place/date you want and the boys can follow.
• DO make nice with the Resort sales staff and head professional as much as possible prior to the trip. We’ve gotten free vouchers, extra deals, and cool swag through this staff.  Again, they want you to return for future trips, so make them earn it.
• DON’T play the tees that you normally would with players of your own ilk. As Dr. Phil would say: “It’s Not About You!”  Most of our guys are 15-25 handicaps, so playing courses that are slopes of 140 and 6700 yards is just stupid.  We tend to play the traditional middle white tees that are 6200-6400 yards a blast for everyone.
• DO remember to take a group picture with everyone at the Flagship course before you leave.