The annual buddies trip is one of the highlights of the year. But it certainly brings its challenges. Most trips that fall apart don't fall apart because of weather or bad golf — they fall apart because the organizer didn't plan for the things that aren't golf. Format confusion on day one, math arguments on day two, money disputes on the last night, and one quiet text in the group chat next March: "I think I'll sit this year out."
Here's a survival guide for the friend who runs the trip.
Making decisions
Dudes are supposed to be agreeable. But getting a group of guys to agree on dates and location for a golf trip is rarely simple. It only gets worse as the group size grows, and decision-making is relegated to the group chat.
Two dudes aren't checking their phones, a couple others can't help but post GIFs from The Office, a few just keep saying "I'm cool with whatever," and two others are already getting nervous about the spend.
If you're the planner of the group, you also are the salesperson. You can't tiptoe around it. Do the research, and propose an idea or two. Don't ask broad open-ended questions in the group chat — there will never be full agreement.
Once you throw out an idea, ask "Does this not work for anyone?" or "Is anyone opposed to this?" People, even your boys, are naturally inclined to say no. In this way, you get everyone to say "yes" by saying "no."
Before you leave: book early, lock the format
Prime destinations can book 12+ months out. If your group hasn't committed to dates by January, you're picking from leftovers for the fall trip.
So congrats — you've got everyone to agree on dates and location. Once tee times, lodging, and flights are booked (and assuming nobody has committed a trip-threatening assault by this point), the next major piece is deciding the format.
Again, don't ask everyone what they want to do. Propose a plan and ask if anyone is opposed. Let them say "no."
The most fun format is a Ryder Cup–style team contest with a running individual stroke play contest across all rounds. This means everyone plays their own ball the whole trip.
The team element adds a wrinkle of competition that gets a buzz going, and prevents a simple stroke play contest that is out of hand after a couple rounds.
Most prefer to start with a low-stakes game, typically Best Ball. The middle days can open up with games like High/Low, Vegas, Best Ball Nassau, Team Skins, or otherwise. And the last round is generally reserved for 1-v-1 pairings — match play or Nassau are the defaults.
Specify if you're using gross or net scoring. It's likely your group has at least some disparity in talent level, and if that's the case, net scoring is the way to go.
Picking teams
If you're going for simplicity, do a random drawing.
If you're going for fun, find a way to pick captains and conduct a snake draft. This could be done the night before the first round (downside is less time to get the group chat going) or done over text/Zoom if the guys are geographically scattered.
On the trip: the multi-day leaderboard is where most groups break
A single round of skins is easy to track. Four rounds across three days with two formats, Ryder Cup points, and per-player handicaps is not. Without a system, the "running leaderboard" becomes whatever the loudest guy at dinner remembers and math disputes. By Sunday night nobody actually knows who won.
You've spent months planning this, only for the competition to completely fizzle.
But if done right, the competition provides an exclamation point on the trip, making next year a must-attend event.
The fix is a real running leaderboard everyone can see — same source of truth, updated live, no recounts, no "wait, are you sure you popped on 14?" arguments. ForeBoard handles multi-round, multi-day, mixed-format scoring — set up the trip once, pick the format for each round, and the team and individual leaderboards update across all days automatically. Free, no app downloads for the players, no software fees for you.
The non-golf details that actually decide the trip
The golf is the easy part. The trip lives or dies on the stuff around it.
Food. Either you organize meals or you can spend too much time debating where to go. Make a reservation for at least one group dinner per night before you arrive.
Rooms. This can get tricky because most trips have at least a couple guys who aren't part of "the usual" group. Do you volunteer to stay with them because you feel bad? Do you text your closer buddies on the side and leave everyone else to figure it out?
Cars and arrivals. Don't overlook this. Eight guys with luggage and golf bags take up a lot of space. This means multiple Ubers, or organizing a shuttle. Especially if visiting a remote location, like Bandon.
Trip-captain calls. Weather delays, format adjustments for slow play, breaking ties on side games — somebody has to be the decision-maker. The group is happier when one person has the gavel, even if the gavel is informal.
Settling up before you leave the resort
Side game pots, skin payouts, individual bets, dinner splits, surprise greens fees on day three — get all of it reconciled before anyone gets to the airport. The Venmo thread three weeks later is where resentment can grow.
Track money in categories — greens fees, accommodation, food, side games — so people can see what they actually owe vs. what they're being asked to chip in for. One source of truth (Google doc, shared note, etc.) is worth ten "I think we're square" conversations.
What makes next year's trip happen
The trips that go 10+ years in a row share a few habits. Format choices that don't let one guy dominate. A scoring system that doesn't generate arguments. Money settled before everyone leaves. A recap text on Monday with the leaderboard, a few photos, and the inside joke from Saturday night.
The annual trip dies when one person stops feeling welcome. Everything else is logistics.
Running a trip this year? Set up your buddies trip on ForeBoard → Multi-round, multi-day, mixed-format scoring with live team and individual leaderboards. Free. No app for the players to download, no software fee for you.
