My annual golf trip is the apex of my golf season. For months leading up to it, I scour the internet for slice-fixing drills, I analyze my swing using my iPhone’s slow-motion camera, and I skip the course to instead hit the chipping and putting areas. This year, I even bought a putting mat for my living room to solidify my 5-footer confidence. And I’m not the only one pumped for our annual trip. We have guys making promotional flyers (a form of taunting using Photoshop), hype videos, and our team captains held multiple Zoom meetings to discuss rules, draft teams, and talk smack.
With several years of experience hosting golf trips, here is a list of 10 best practices that will lead to the ultimate golf trip.
1. Choose a good location
You don’t have to go to Bandon Dunes or Pinehurst for an awesome golf trip. However, location is important. Choose a location with several quality golf courses within a short distance of each other. The Robert Trent Jones Golf Trail, Fairfield Glade, and many metropolitan areas can be hosts to a great weekend.
2. Set the right schedule
When scheduling your tee times, it’s important to know the energy level of your group. Even for shorter trips, 36-hole days can still be brutal depending on the weather. We suggest playing a “fun” afternoon round. Find a good par 3 course to play barefoot, include a drinking game on the scorecard, or play a 2- or 4-man scramble to mix up the afternoon rounds.
3. Include clusters of skill levels
You want to invite people who both fit in with the group and have comparable skill levels to at least two other members of the group. Handicapping is a great way to level the playing field, so don’t be afraid to invite some higher or lower handicappers if you feel they will be a good addition to the group. It is best to avoid non-golfers, no matter how well they get along with the group. You, they, nor the group behind you, will enjoy the trip.
4. Choose the right games
There are a lot of golf games out there. We typically play 9-hole matches and swap games after each nine. Each individual hole can be played as a point for your team (9 points per 9-holes) or each 9-hole match can be played as a point for your team (1 point per 9-holes). Choosing a point system typically depends on how many teams are involved and how many rounds will be played.
Here are a few of our favorite games for team events:
- Best Ball Match Play – best for opening rounds while high-handicappers dust off the cobwebs.
- Low Ball, Low Total (+1 birdies, +2 eagles) – a high-scoring format that involves both members of each pairing and incentivizes more aggressive play.
- Stableford or Quota – great for an afternoon round (because double bogey max) and pairs nicely with a drinking game.
- Singles Match Play – a group favorite- match players up with a bitter rival.
- Alternate Shot – great if you’re not playing a stroke play event at the same time.
- Dogfight – check out our Dogfight event here.
5. Pick captains and draft teams
I typically start organizing the competition by choosing the number of teams. For a group of 12, we typically play 6 vs 6. This year, however, we played 3 teams of 4. While a bit more work, I found 3 teams of 4 more enjoyable because each member has more impact on the outcome (1/4th of the team score as opposed to 1/6th). Once the number of teams is set, choose your captains. As the “game-maker,” you may think it would be best to set teams and match-ups. While this may be true, it is much more fun to pick captains and allow them to draft their own teams. This also allows you to do some arbitrary handicapping (estimating a handicap for someone who doesn’t play enough golf to have a handicap) without being accused of “rigging” the game. More on handicapping in the next section.
6. Take the pressure off of handicapping
Set handicaps for each player prior to the draft, then allow the captains to draft players based on the captain’s perceived value of each player. For example, if Captain A believes Jack is getting more strokes than he deserves, he is more likely to pick him in an earlier round. This takes all the pressure off of accurate handicapping. This is important because many weekend golfers don’t have official handicaps. View my article on how to calculate your official or unofficial handicap. What you’ll likely find is that captains will take the best golfers first regardless of handicap. In my experience, this is a mistake. Captains should seriously consider taking a higher-handicapped, more volatile player over the scratch golfer. While the handicapping of the draft pool of players doesn’t have to be perfect, try to make sure your captains have fairly accurate handicaps (relative to each other) to avoid any major difference in captain value. If you still want to improve your group’s handicap estimations, consider setting up a golf league with your friends!
7. Simplify the rules
If you have a group of die-hard competitive golfers in your group, skip this section. Otherwise, consider playing by alternate rules to make play more fun and to speed up the pace of play. Here are a few of the favorites that we always play by:
- Alternative Out of Bounds and Lost Balls – We usually play everything (OB, unmarked tall grass or thick woods) as if it were a lateral water hazard (“take relief back on a line behind any water hazard (Rule 26-1b) or within two club-lengths of where a ball entered a lateral water hazard.”). This keeps from having to go back to the tee to replay a shot and is especially important on tight courses. For more serious players, you may prefer to play by the new Alternate OB rules which are much less forgiving (2-stroke penalty instead of one).
- Triple Bogey Max – For better groups, you may want to consider a double bogey maximum. However, for groups with multiple players shooting their temperature or worse, a triple bogey max gives them a little more to play for.
- Play it up / Free Relief – Nobody wants to scratch their brand new Vokey wedge chipping off of a rock. Allowing a scorecard length relief from rocks and tree roots prevents both club damage and cheating (because someone in your group will do this anyway). If you want to eliminate the chance of illegally improving lies, play it up everywhere!
- Gimmes – In a pressure-packed final round with big (or small) money on the line, gimmes may take away from the fun. However, in early rounds, we tend to play putter-length or inside-the-metal-length gimmes to speed up play.
8. The Calcutta – End things with a bang
Full disclosure: this is my favorite. A Calcutta is a handicapped event where other members of the group get to “buy” players in an auction prior to the Calcutta round. We play this during our last round of the weekend so that we can use prior rounds to set handicaps. Once a player is bought in a live auction, they have the option to buy 50% equity in themselves for half the bid price. This year, our worst golfer, who went for a measly $15 and didn’t even bother to buy half of himself, took home the victory (but not the cash). His “owner” was kind enough to give him a portion of the thirty-fold winnings. Visit my post on How to Improve Your Golf Trip – “The Calcutta” (with virtual scorecard)! to learn how to set up your Calcutta with a virtual scorecard!
9. Create a one-pager with the schedule and rules
Organizing your golf trip is not easy. Even harder: explaining the competition to your peers. Be sure to print off a one-page sheet that lists the teams, tee times, games, and rules. Simply telling your group to look at your email or the shared Google Doc will not work (I know from experience). Printing it out will save you time and effort having to re-explain the rules to your group and other groups during your round.
10. Include “extra stuff” for “extra fun”
Every year we mix up our games and add a little more flair to our event. Here are a few that have worked well:
- Prop Betting Pool – Use a Google Form to set up “prop bets.” One of the highlights of this year was “Will Player X top his first tee shot?” On the first tee (and the night before), he was sweating bullets thinking about his opening tee shot with all 11 others watching him. I wish I could tell you this is a feel-good story of overcoming his fear, but…his tee shot didn’t go 20 yards. Sorry X. Check out my post on Prop Bet ideas!
- Virtual Scorecard – This was a game-changer. Having a Google Sheet that automatically converted handicaps (no math!) and kept up with live scoring allowed everyone to know where they and their team stood in the standings as our team event came to a close. Knowing “we are trailing by 3 going into hole number 18” or “I need to birdie number 18 to win” was very exciting and much more efficient than trying to communicate the score through a stream of text messages. I will have future posts on how to set up a Virtual Scorecard with a Google Sheet, so please subscribe!
- Snakes – We play Snakes differently. It gets personal. In this game, you can choose to call “snake” on any player prior to him approaching his putt (defining “approach” is a gray area that has led to some minor conflict). If he three-putts or worse, he gives you $1. Otherwise, you pay him $2 for converting a difficult two-putt. There are many variations of Snake. While this one is easier on the wallet than most, it does allow for some gamesmanship about who, when, and how often to sound the dreaded “snake” call.
Conclusion
Teams are set. Smack talk is blowing up your iPhone and your 10-handicap friend is trying to convince the group he’s playing at a 4 (he won’t break 90). You’ve got a few sleeves of your favorite performance golf balls (my favorite is the Srixon Z-Star) all marked up and ready to go. The trip hasn’t even started yet and you already feel like the trip is a success. You’ve put in the time to organize everything and gone the extra mile to make things fun. Now it’s time to enjoy the spoils of your hard work! Hopefully, you didn’t forget to practice while planning your trip!
Please let me know in the comments what else should be added to this list!

One thought on “How to plan a Golf Trip”