Lessons learned from my first buddies-trip captain experience

Last month, I captained my first buddies golf trip. It was hardly perfect. With the responsibility of the captain's chair comes a lot of analysis on the flight home and days following. What went right? Where did I blow it?

I've been on the golf travel beat for over a decade now, but this was my first true group golf trip with no work commitments attached. It's one thing for a media junket to go south (and they do), but it's quite another when you and your buddies have coughed up hard-earned money and talked your way into a long-weekend away from the wife and kids.

The pressure of a three-footer pales in comparison.

Fortunately, the worst-case scenarios - lost tee times, bed bugs, jail - were avoided. Here's what I learned my first go around. I'm eager to hear your thoughts and suggestions for next time.

They say your first buddies trip should be a small group. In hindsight, I probably should have heeded that advice, but it was tough to do. I had a core group of three college buddies who were all over me to pull the trigger on a trip last fall, quite literally as my wife was due for our second child. They persisted and I ultimately caved. We thought it might be good if we expanded the group to 8. Lo and behold, 9 were keenly interested, but it was a struggle getting to 12.

Those last three spots were a revolving door for months: Committing, then backing out, verbally committing, sending me deposit money then asking for it back. Excuses ran the gamut. One guy broke his arm snowboarding; fair enough. Others backed out for flakier reasons. I'm told that being a captain is a "dictatorship" but what am I supposed to do, not give their $500 deposit back?

Lining up the 12 people proved to be the biggest headache of the trip. Not only did I want a legit Ryder Cup match, but Torrey Pines has a non-refundable $45 booking fee per person I didn't want to swallow.

Ultimately we had 10 for the arrival day round, 11 for the Friday round and 12 for the Saturday round at Torrey. You can't have the excitement of a full-on team event like that, but we still figured out some imperfect individual and team games. I probably shouldn't have fretted over the head count so much.

One thing that bothered me a little about ending up with the 11-12 folks is I barely got to catch up with the core group of college buddies. But overall, the group got along and new friends were made.

May is a tricky time to plan a golf trip because while the entire country is open for business, many destinations are in shoulder season. With most of our group living between Texas, Colorado and Michigan, I picked San Diego for the reliable weather but also the abundance of short courses and even some chances to walk. San Diego has a convenient airport, good restaurants and a variety of courses, but as the designated herder of cats on holiday I also liked the idea the nightlife would be a little more restrained than Las Vegas or New Orleans.

Ultimately, the golf worked out, and our out-of-pocket expense for three nice courses was about $350, about my goal. Several of us also played executive courses in the evening while others took in a Padres game or went to the Gaslamp district or waterfront. Some had never taken Bird Scooters before so they enjoyed cruising around the city. Recent state legislation pertaining to the legality of marijuana pleased others. We got very lucky with the weather; it was raining when we landed and rained when we left, but all the golf was played dry. There's no such thing as a surefire May weather destination, but San Diego delivered for us.

Short courses in San Diego

Golf under the lights at Mission Bay Golf Course near downtown San Diego. Brandon Tucker/GolfPass

Playing 'ready golf' at Oaks North, an 18-hole executive course near Maderas Golf Club. Brandon Tucker/Golf Advisor

I thought a reasonable budget for room and golf for three nights would be about $600 per person. From the start, I was clear with prospective attendees that that was my aim and asked for $500 up front. In San Diego, you can definitely splurge by going up to Carlsbad but I chose not to. This meant we had to pass on Fairmont Grand Del Mar, Aviara or Omni La Costa, but I felt my group, about half of whom are relatively new to the game, wouldn't appreciate all the bells and whistles of those joints, even though several guys in my group seemed willing to splurge on anything.

For group meals and tee times, I paid the full tab and just split it up evenly after the trip using the Golf Genius Trip Manager software, an app that is geared towards buddies-trip captains and tournament organizers. Using Trip Manager the first time, you sense how detailed and powerful it can be, but there is a learning curve for first-time users. Fortunately, customer support is readily available if you have questions and there is a detailed FAQ and support page I referenced regularly.

One note on collecting funds: Some friends use Venmo while others prefer Paypal. What you don't want to do is try and collect cash on the fly. After our round at Torrey Pines, I made the mistake of announcing what people owed me for the games pot and next thing I knew I had cash flying at me from all directions. I'd been on the golf course all day sucking down various drinks from the first hole to the 19th under the sun - hardly the state of mind to be an accountant. It took some time after the trip to be confident in the bookkeeping. And I'm glad to report I didn't have to hunt anyone down for funds owed.

San Diego runs very deep with courses of all styles, and few destinations are as synonymous with muni golf thanks largely to Torrey Pines and Coronado.

Booking groups at munis, particular wildly popular ones, isn't easy. I ultimately couldn't line up three consecutive tee times at mega-popular Coronado, which had too many outings and tournaments on the books. You also can't book tee times there until 14 days in advance, which can be nerve-wracking for a trip captain. (I had been teasing the round at Coronado from the genesis of the trip). When I realized Coronado couldn't happen, I thought I'd try a military course; they come highly regarded and are good values. But while Sea n' Air does allow sponsored civilian play, it's very difficult getting on the base to do so, and Admiral Baker had a tournament as well.

Fortunately I was able to find three times at Steele Canyon Golf Club - a good option that had a great twilight rate and dazzled with scenery on the Canyon nine and was well-conditioned - for our arrival-day round. Its location meant more miles in the car and had more of a target-style layout than I wanted our group to play after having just gotten off the plane (I also would have preferred a flatter walking course), but it kept the trip on budget and was a good first impression.

When I settled on San Diego, I knew the slam dunk would be Maderas Golf Club, though I did warn our higher handicaps it'd likely be their biggest score of the trip. I visited years ago and the Troon-managed facility was one of the best member-for-a-day experiences I'd seen. Green fees are less than the Carlsbad resorts but the layout is arguably better. It's just not close to the ocean and doesn't have a luxury resort brand attached.

For the finale, I had to go with Torrey Pines and scored three late-morning tee times on a gorgeous Saturday morning about 75 days out (they begin accepting 90 days in advance). I was glad Torrey Pines South was all chewed up in preparation for the 2021 U.S. Open, because it gave me a more convincing case to steer my group to the more pleasant (and slightly less pricey) North Course. But I was bummed to learn that we'd be playing the course nine days after the greens were aerified and there was no price break. Torrey North's greens weren't too bad, but Maderas' and Steele Canyon's were perfect.

While I could email back and forth with group directors at Steele Canyon and Maderas, I had to call Torrey Pines during business hours and the line was often busy. Privately-managed courses will wheel and deal with larger groups; good luck doing that at Torrey Pines or Coronado.

The Trip Manager portal provides a variety of stats, and as expected, Torrey North with its less penal parkland layout was six shots easier than Maderas (97 to 103). I assumed this, coupled with the views would make it the group's favorite, but I was wrong. Pretty much everyone preferred the value, facilities, condition and layout of Maderas. Just as we all knew, amateur golfers love a good beatdown.

The lesson? Have backup courses in mind if your ideal roster includes a course that ends up falling through. Don't announce specific courses to your group until they are confirmed or some may feel disappointed. I might also look into a stay-and-play at a resort instead of doing daily fees next time.

Live scoring and handicapping is where the Trip Manager software powered by Golf Genius shines, and it explains why so many directors of golf trust it for competitions at their clubs. We had a wide range of handicaps: 6 to 28. It also came in handy because we had a different number of players each day.

Prior to the trip, I used the software to set up pairings and added courses and selected tee boxes, which loaded slope/ratings. Then I added a daily skins game and a different team game for each round. (Blind best-ball, then a group best-ball, then a Ryder Cup team best-ball match). You can go down a serious rabbit hole with all the games available on Golf Genius. Some were totally foreign to me; likely staples of the private club world. I kept my games relatively simple, and leaned on net Stableford formats.

I was able to get enough of the participants to download the mobile app so someone in each pairing could enter in scores after every hole and create a mobile scoreboard. You could see live team and skins results. At the end of the round there were no strokes or purse calculations. The time spent setting everything up paid dividends at the 19th hole. I could relax like everyone else.

It was tough to properly handicap the group because only half of us kept official GHIN indexes, the others were saying things like "I shoot around 95 I guess" or "I don't keep score." Ultimately, those of us with the lowest handicaps won the least amount of skins and most of the higher handicaps raked in the cash. My Golf Genius settings handicapped at 100%. Next year I may go down to 80-90%. Or maybe I just need to play better.

Remember I mentioned the guy who broke his arm? He made a Hogan/Tiger-esque recovery and felt well enough to make the trip anyways and even play Saturday at Torrey Pines (I was thankful because of the non-refundable $45 deposit per golfer I paid before his accident). So on that day we were able to have a legit 6-on-6 Ryder Cup competition. Mission accomplished.

I settled on a full-house AirBnB in Pacific Beach. It was big in a nice location within walking (or scooter) distance to bars and restaurants at a decent price, but not everyone got a bed. Some ended up on pullout couches or futons. There was also a shortage of linens and towels and the place was minimally stocked. The owner also scared the daylights out of me on arrival when he said that neighbors were aggressively calling the police on vacation renters and their previous group was evicted and received a $1,000 fine. My group, while more mature than our college days, still had some loose cannons and it led to some nervous nights for me as I waited for the late-night stragglers to stumble in. The group had its shenanigans but fortunately they weren't excessively noisy and things worked out.

But we never had time to stock the fridge or cook, and it would have been nice for everyone to get a proper bed and enough towels. Staying in a beach town was also silly because we forgot that it can be chilly in San Diego in May, and it's also well off the highway arteries. Kiawah Island this was not. Next time I may inquire about a golf package like this one for $227 per night that includes La Costa and Maderas.

When I was in my early twenties, many of my closest friends didn't play golf. Now that we're in our 30s, most of us with kids, it's been a thrill for me to see them getting into the game. It's just more fun to spend the day on the course together than on a bar crawl or in a casino or, God-forbid, camping. Prior to the trip, several were calling me with questions about lessons and buying new equipment. Once the group text was formed the GIFs got weird.

Even though I felt a kind of obligation to show off what I know having been in the business for awhile, I didn't want our trip to be all about playing the best courses. I wanted to make sure the newcomers to the sport wouldn't feel out of place, and ideally everyone would have a moment or two of glory. I think all the guys left with a desire to play more. Hopefully real life doesn't get in the way too much.

Thinking about next year, we could just as easily return to San Diego, or maybe we'll try somewhere to the north or east. Or maybe the desert. Considering most of my group felt underwhelmed by the $200 course on our trip, maybe we'll steer more towards value. Our text chain is still alive a month later, and the ideas are already flowing. So is the trashtalk.