The Complete Golf Buddies’ Trip Checklist

Playing golf by yourself can be sublime—like when you’re sneaking in a few holes at sunset after work. Going out as a single with strangers can be rewarding, too, especially if you’ve queued from 5 a.m. to get out on the Old Course and exit the 18th green with three new friends.

But the best golf is the golf you get to play with old friends—or family members. Guys (or gals) you wish you could see more often—like my close friends Doug and Ray, with whom I’ve gone on a bunch of trips over the years. Even better are the too-infrequent opportunities to take a golf trip with your best pals to some far-flung bucket-list destination. You want to make the most of those chances.

Here’s a checklist to help you do that.

Golf Buddies Trip
On the 17th tee at St. Andrews (photo by David DeSmith)

1. WHO

Traveling with others can be equal parts joy and stress. To avoid the latter, choose your fellow road warriors carefully. That guy who complains about everything may be tolerable in small doses, but a steady diet of him over the course of a week may not go down well. Large groups (more than eight) can also create logistical challenges. Confine your group to no more than one or two foursomes, and if you’re not sure whether a player can go the distance, consider leaving him or her off the invite list.


Any place can be special when you’re with good friends. But given the time and expense that goes into a buddies’ trip, you need to make sure the majority of the courses you’ll be playing are first-rate. At the end of the day, food is food. A hotel room is a hotel room. But every time you set foot on a new first tee, it’s like opening a present. Whether you’re staying in the U.S. or venturing overseas, play the best courses you can, with a lesser-known gem or two thrown in for variety.

Golf Buddies Trip
My son tees off at Royal County Down (photo by David DeSmith)


It’s never easy to find a window that works for everyone. But I like to target the months of June and July. Why? There’s more daylight, which gives you the option of playing 36 without rushing—or to rejigger your tee times in case of bad weather. Shoulder seasons are normally cheaper, and winter golf down south is always welcome. But you gotta love those long summer days.

4. HOW

Once you’ve agreed on your dates and destination, pick an organizer—preferably someone who’s a stickler for details. Then, everyone else get out of the way. You’ll want consensus on details like how many rounds, how much you wish to spend, and other activities on top of golf. You can share info and opinions back and forth on a private Facebook page or Google doc, but planning a trip by committee usually ends in disaster—so don’t go there!

If you can, use a tour operator. They do so much for so little upcharge, and they can recommend special experiences along the way that would never even occur to you. If you can’t use a tour op, at least hire a transportation provider. For groups of more than four, this is a must. But even when you’re just a foursome, if your trip will involve any appreciable amount of time on the road you should leave the driving to someone who isn’t just coming off a career round and eager to celebrate. Nothing beats the taste of a cold post-round beer when you’re relaxing in a comfortable coach. And in truth, no rental vehicle that supposedly seats four will ever be big enough for four players plus their clubs and luggage. Trust me on this.

Golf Buddies Trip
(photo by David DeSmith)

You also need to give some thought to sleeping arrangements. Yes, sharing rooms is cheaper, but nobody wants to be kept up all night by a roommate’s buzz-saw snoring. Separate rooms give everyone privacy—and room to decompress.

Finally, whenever possible, try to take advantage of stay-and-play packages. Those kinds of discounts really add up when multiplied by a bunch of travelers.


Just spending time with close friends is special. Add in golf, and it’s a can’t-miss situation. But it’s often the little things that everyone remembers most fondly. Consider a group gift—customized balls or a hat or shirt. Include some “tournament” rounds for prizes (flasks make good trophies). Bring glow-in-the-dark balls and see if you can squeeze in a couple holes of night golf or a postprandial putting contest.

Make sure to also leave time for non-golf adventures. Take in a historic site or natural wonder. Visit a winery or distillery. Make reservations at a few special restaurants. And when you get home, create a Dropbox file or Google page where everyone can upload their favorite photos and videos. Those memories will sustain you until the next time you can hit the road together.

Enjoying a beverage outside the Dunvegan Hotel in St. Andrews (photo by David DeSmith)

Ever been on a buddies’ golf trip? Let us know your best tips in the comments section below.