My regular golf buddies and I have taken many trips together, and, by trial and error, we've learned a lot about what works and what doesn't. Here are some tips:
__DO__give one person the overall responsibility for managing the itinerary, keeping track of reservation deadlines, reminding laggards to make their deposits, and deciding which minor tasks can safely be delegated. Having a single, reliable leader makes it less likely that critical details (such as tee times) will be forgotten and creates a clear blame path if things go wrong.
__DON'T__automatically assume that nobody will be up for more than 18 holes a day or (equally important) that everybody will. During a buddies trip that eight friends and I took to Scotland this past spring, we designated one round as the official 18 for each day, so that oldsters could flake out in the afternoon without losing their place in the standings. On the final day of an earlier, 10-day trip to Ireland, when even the golf obsessives had begun to fade, we revived everyone's spirits by playing a scramble in the afternoon.
DO establish a centralized rule-making authority with the power to silence whiners, naysayers and independent thinkers. Among my friends, this authority is called the Committee, and it typically consists of Hacker (real name) plus one or two people who, over the years, have satisfied Hacker that they are likely to agree with him. The Committee has many responsibilities, including picking the games, choosing the stakes, deciding whether Gene will be allowed to play from the senior tees, and settling minor but potentially divisive issues as they arise, such as do we get a first-tee do-over or not? The Committee's decision is always final -- a relief to most people, who go on golf trips to escape responsibilities, not to acquire new ones.
__DON'T__allow trip-threatening behavior to go unpunished. On the second morning of our annual Atlantic City trip a few years ago, one foursome drove to the wrong golf course, even though all five cars had left our hotel at the same time and everybody had been given printed driving directions. The resulting confusion came close to ruining the whole trip, or so we said. When the round was over, we restored order by conducting a trial in the clubhouse -- taking advantage of the fact that two participants that year were lawyers -- and sentenced the offenders to pay for everybody's lunch.
__DO__collect all wagers before anyone tees off. Losers always outnumber winners, and on a large golf trip that means that if the prize money isn't in hand when the scores are tabulated, the victors will have to collect from a sullen mob. We handle this on our golf trips by assessing a single ante on the first morning -- currently, 100 bucks a man -- and paying all prizes for the whole trip out of that fund.
DON'T let the stakes get out of hand. The purpose of playing for money is to make three-foot putts seem important, not to let anyone get rich. We try to spread the prize money around by having lots of complicated side bets, all paid off from the same 100 bucks.
__DO__establish community-building trip traditions, such as only ordering bacon cheeseburgers for lunch and always allowing non-drinkers to drink free.
DON'Tfeel you have to do everything as a group. We often split up for dinner, primarily to eliminate tedious arguments about who is willing to pay how much to eat what. Doing this also occasionally generates interesting demographic data, as it did when (as someone realized later) all the Democrats went to a sushi bar while all the Republicans went to Outback.
DO be careful about the guest list. We usually open our trips to friends from outside our club, and even to friends of friends. This has beneficially expanded our acquaintance with overweight middle-age men from outside our immediate geographical area, but it has occasionally led to problems. One year, one guy invited an old high-school friend of his, whom he hadn't seen in years. The old friend, who began drinking as soon as he got into Hacker's car, bought a dozen condoms at a convenience store during the first refueling stop, then stashed the box under his seat and forgot all about it. A week after we got back, Hacker's wife discovered the condoms and -- here's the problem -- wasn't concerned, even for a minute, that they belonged to any of us.
DON'T let a buddies trip end without establishing a Committee to pick the next destination.