How to Plan a Buddy Trip

It’s time for a buddy trip. Time to get away from it all with friends and spend quality time, strengthening those age-old bonds between men and, if it’s an epic trip, perhaps even testing them. While there’s no buddy trip blueprint, pop culture has given us plenty of archetypes to work with — the classic road trip of discovery, the fishing trip gone awry, the booze-soaked weekend in Vegas, the adventure turned survival trip — that are either impractical in real life or fall short of expectations.

There are a handful of challenges to planning a buddy trip that separate it from your standard solo or soulmate trip: you don’t share finances with your buddies, you probably don’t have similar schedules, and you probably don’t live together — possibly not even near each other. On the flip side, there are also opportunities that can make it a different and, in its own right, more interesting trip: stupid hilarity is more likely to occur, especially if you’ve known your friends from college age or earlier, when doing stupid stuff was second nature; peer pressure plays a much bigger role here than on other trips, which pushes boundaries; and for the dads out there, bigger risks can be justified (at least they’ll still have a mom, right?).

So how do you plan an unforgettable buddy trip, an epic that you’ll be talking about for years to come? We asked Greg Sacks, founding partner of Canadian custom travel company Trufflepig, for guidance. He’s been creating such trips for well-heeled clients the world over for more than a decade, and spearheading them with his own mates even longer. His tips, while deliciously simple, are aimed towards elevating any buddy trip into something more memorable and lasting.

The Guidelines

1 Agree on goals. Figure out what, as a group, you want to get out of the trip. “Is it a bonding trip?” asks Sacks. “A celebratory trip? Are you looking to come back with mind-blowing pictures? Do you want to come back with a physical high? What are the key things you want to achieve?” Answering these questions and getting everyone on the same page at the outset not only helps shape the trip, it also stamps out competing agendas, making for a smoother planning process.

2 Challenge yourselves. Part of the purpose of taking a buddy trip — and, indeed, part of what makes travel of any kind transformative — is to step outside your well trod routines and discover something new about yourself or your friends. Giving yourselves a challenge, be it navigating a foreign language, tackling a physical trial or just going somewhere you’ve never been before, can shake up the group dynamic in new and exciting ways.

3 Don’t over-plan. This is a buddy trip, not a mission to Mars. In the age of Google, we’re prone to researching every last little detail of life, from where to grab dinner to which toothbrush is best reviewed on Amazon. And that extends to how we’ll spend every minute of an upcoming trip in an unfamiliar place. But Sacks encourages you to resist, instead leaving ample room for spontaneity. “It’s great, in this day and age, to feel a lack of control,” he says, adding that the real magic typically happens in the unplanned moments. “If you plan the shit out of your trip and you don’t leave any room for that, you rob yourself of discovery.”

4 Plan for serendipity. “Put yourself in a place of serendipity,” says Sacks. Though it sounds completely counterintuitive, what he’s saying is that a certain intentionality in planning can go a long way toward making cool, unexpected things happen. “Build in as much possibility for surprise and the unexpected as you possibly can.” For example he planned a trip to Malawi in which his clients used traditional fishermen‘s dugout canoes to paddle a five-day route up Lake Malawi. The catch was that said canoes are tippy as hell, and don’t track very well. “While at first it seemed ridiculous and not doable, they had to figure it out or they’d have been lost on the trip — it was a make-or-break situation.”

5 Talk to strangers. “When you meet people who weren’t part of the plan,” Sacks says, “things happen.” Not only does it disrupt the all-too-familiar dynamic of longtime friends, it also opens the group up to unforeseen possibility, and that magic sauce of serendipity. But how to force such interactions? Sacks suggests omitting certain logistical details — such as doing a point-to-point hike without setting up a shuttle — that force you to figure it out in real time (most likely hitchhiking or otherwise bumming a ride, in this case). “It can break down the code a bit, and everyone rises to the occasion of a stranger. At first everyone’s slightly uncomfortable, but then it’s quite fun to see how they deal.”

A Few Ideas

1 Learn a skill. A common hurdle to planning a buddy trip, especially one that involves outdoors sports, is vastly differing skill sets among friends. One way around that is to take a trip where the goal is to learn a skill together. Sacks and his buddies took a weeklong mountaineering course in the Canadian Rockies with Yamnuska Mountain Adventures. “It was a really great trip, because it laid the foundation for more years of great mountaineering trips,” he says. Whether you’re into mountaineering, paddling, rock climbing or even fly fishing, taking an instructional trip is a great way to grow together and set yourselves up for self-guided adventures down the line.

2 Take an analog road trip. Treat your smartphone like, well, a phone. Navigate by map and guidebook instead of Google Maps; ask locals for directions and inside intel — restaurant and hotel recommendations, for example — instead of asking Yelp, Tripadvisor and Kayak. Don’t make reservations. Do that, and you’ll likely discover something new about yourself, as well as boatloads of road magic. A few classic road trip routes include Grand Canyon to Moab, Jackson Hole to Glacier National Park and the California Coast

3 Track an animal. Be sure to pick something that’s fairly rare and/or elusive, like wolves in Yellowstone, a rhinoceros in Namibia or, the ultimate, a Himalayan snow leopard. You don’t know if you’ll find what you’re looking for, but you’re guaranteed adventure and quality time outdoors.

4 Accomplish something. The more tangible, the better. Climb a mountain, say. Washington’s volcanic Mt. Rainier and Wyoming’s Grand Teton are both serious mountains that, with minimal training and a guide, are fairly beginner friendly. Paddle a modest river from source to sea. Mountain bike from Durango to Moab. Run with the bulls.

The Devil’s in the Details
While there aren’t many hard-and-fast rules for planning a great buddy trip, there are a few surefire ways to screw it up. Here’s how to avoid ‘em, with pointers from Kate Warner of luxury travel planner Black Tomato.

1. Talk about money (it’s awkward, we know), and settle on a budget that’s reasonable for everyone.
2. In the same vein, create a “kitty” (like in poker) for headache-free group spending, and entrust it to one responsible person.
3. Plan enough, lest endless on-the-fly decisions interrupt the trip’s flow, feel like work and result in strong-willed buddies hijacking the trip.
4. Nominate a responsible buddy to organize tickets, accommodations, etc. on behalf of the group.
5. Avoid the dreaded email chain by creating a more streamlined private Facebook group for trip planning.
6. Plan a mini trip to prep for, and plan, a big trip. Or, if you’re local, meet regularly at the pub until you’ve hacked out a plan. Then pretend you haven’t, and keep meeting anyway.

For inspiration on where to go, check out our 25 Best Places to Travel in 2015.

Related Topics