Your boss. Your girlfriend. That guy in the pro shop. Don't give anyone a chance to say you can't go on this golf trip. To ensure universal approval and to nab your desired tee times, start planning six to twelve months in advance. Be upfront about the amount of time you'll spend away from home, and overestimate the amount of time you'll be away from your cell phone and computer. This lead time also means a greater number of emails and text messages exchanged among your golf buddies. Who doesn't love that?
Nothing's more important than who you invite
A group of buddies could just as easily visit the world's worst golf resort and have a blast as it could travel to Pebble Beach and be miserable. More than lodging, food, weather and even the golf courses, the people you bring are key. Buddies trips take you out of your comfort zone. You're away from home, sleeping less than usual, playing unfamiliar courses, competing hard, drinking copiously. This isn't the time to introduce your pals to a friend who "might" irritate the hell out of them. He will, and the trip will suffer because of it.
Have a dictator
There is a time and a place for democracy, but a golf trip isn't it. Too many opinions about courses, hotels, formats -- you name it -- risk making every decision unnecessarily complicated. Instead, pick someone who you all trust to lead the way and allow him or her to delegate responsibility. Maybe one of you is in charge of pairings. Someone else can pick the dinner spots. You don't have to love every decision they make. But trust us, it sure beats not getting anything done at all.
Establish the ground rules early for money
Chances are you'll know beforehand how much you're spending on lodging, golf and transportation. But gambling? Food and drink? Other off-course stuff? It helps a lot if your trip leader can give some direction on this before you go. All it takes is a simple note added to the itinerary: We eat dinners as a group and the bill is typically $40 a man, etc. Also, your life will be far simpler if you have one person pay for it all and then split the total evenly at the end. One more note worth adding to the itinerary: There will be no quibbling over who ordered what.
Have an off-course plan
Hopefully, you've planned a decent-length trip, but even so, the last thing you want to do is waste time deciding which chain restaurant to go for dinner. Know your options in advance so you're not looking things up and make quick decisions. Are you really going to remember where you eat? No, you're going to remember hanging out with your friends. You'll get to do more of that if you come prepared. Same goes for nightlife. How often do you get to go on vacation with your buds? Stop Googling which local bar makes the best margaritas and get out and enjoy yourselves!
Set the tone early so you know what you're getting into
Is this going to be a play-as-much-golf-as-humanly-possible kind of trip, or will it be a play-18-holes-and-check-out-the-local-hot-spots kind of trip? Establish the tone early so nobody is surprised or disappointed with your itinerary, and so you'll attract like-minded buddies who'll enjoy the trip as much as you will.
Be prepared to play more golf than you're used to
Most buddies trips involve an insane amount of golf, and that's a wonderful thing. Don't let soreness, blisters or fatigue stop you. Stock your golf bag with anti-inflammatories, band-aids, athletic tape and Vaseline. Get plenty of rest before you board the plane, since eight hours of sleep on any given night during a golf trip won't happen. And stretch before and after your round, more than you would otherwise.
Give ample thought to pairings
If you're traveling with a group of people who get along well, there shouldn't be any problems putting together foursomes. That being said, a trip can be enhanced by mixing things up. Don't just ride in a cart with that same guy you also play all your rounds at home with. You should make sure you play with everyone else in the group at least once. Also, groups should be balanced. Don't ever pair four slow players together or four golfers struggling with their golf games. Unless, of course, you're trying to deter certain people from coming on next year's trip ...
Have a formal competition
Every golf trip thirsts for a running storyline, which is what makes a competition that extends from the first day of the trip to the last so inviting. Maybe there's a bunch of cash at stake. Maybe it's all for pride and an ugly plaid jacket. The key is to give each hole you play a broader context. A buddies trip is the closest many of us will get to living the life of a tour pro. The fun part is in seeing how you fare as the pressure builds.
Wagering may add a touch of excitement to your buddies trip, but not gambling can be satisfying too. Really! Think about playing each course purely for the enjoyment of experiencing something new. Imagine not grinding over three-foot putts for double-bogey. Picture your group finishing rounds in less than four hours. These are among the benefits of a gambling-free buddies trip. Sure, there will always be guys who insist that they "need a little something to make it interesting." It's not unreasonable, as you stand on the first tee overlooking a beautiful golf course, to face that person directly and say, "Seriously?"
Either way, don't stress about how you play
You just found a fourth water hazard on the front nine on Day 1? Take a deep breath. For one thing, you're not playing your home course where you've memorized every blade of grass. For another, getting too frustrated won't just ruin your round, it could have a negative effect on your entire trip. Oh yeah, nobody else will want to be around someone who seems miserable and ready to go home. No matter what you're writing on your card, remember that you're on a golf trip with your friends and not stuck in the office.
Take care of the people you leave behind
Odds are if you're taking off for a few days of golf you're leaving someone else in a lurch. Your wife alone with the kids. Your partner at work now covering for two. To show them your appreciation, and most importantly, to alleviate your own guilt, think of something nice that will make your re-entry back to the real world as smooth as possible. Arrange for a sitter so your wife can get out when you're gone. Or send her flowers. Bring your partner back a shirt. This golf trip may be all about you, but you'll enjoy it more if you get others to feel good about it, too.