“Our group proved that a complicated outdoor trip need not only be pursued by expert campers”

Meet Spencer and Aaron, two close friends from college. In 2018, it had been a little under a year since graduation, and both were working demanding professional services jobs – Spencer in Boston and Aaron in Washington, D.C. Both were severely lacking outdoor adventure in their day-to-day lives, a jarring transition after spending their four undergrad years steps away from the White Mountains in New Hampshire.

As the weather started to get warmer and both friends started to feel more settled in their new jobs, Spencer and Aaron realized that they had used very few of their precious vacation days and decided it was time to plan a trip. They polled a few of their other friends and the results were mixed: the avid skiers in the group had already used up most of their time off, and friends working in other industries had less time off to work with. And, looming over it all, was the big question of where to go and what to do – ideas were as far-ranging as motorbiking across Southeast Asia and kayaking in North Carolina’s Outer Banks.

A few weeks passed and virtually no progress had been made. It started to feel like the whole endeavor was about to fall apart. Frustrated, Spencer lamented about this to his roommate, Nate, who had initially opted out of the trip in order to save his vacation days for a trip with his girlfriend’s family. Nate reacted with empathy, and a few loose ideas, but no concrete solutions. Still, Spencer could tell that Nate’s brain was starting to spin.

One or two days later, Nate enthusiastically approached Spencer with a compelling proposition: not only would he like to join Spencer and Aaron on the trip, but he’d also like to take the lead on synthesizing everyone’s preferences and planning the trip. Capacity-constrained at work, and lacking a clear vision for the trip, Spencer was more than happy to offload the planning to Nate.

Nate, Spencer, and Aaron quickly aligned on a week-long, domestic trip that combined their mutual thirst for outdoor adventure with their desire to explore a few new cities: a road trip along the Oregon coast. It was the perfect trip, a budget-friendly way to hike, camp, and enjoy beautiful scenery, all bookended by visits to Portland and San Francisco. The rough itinerary was:

• Day 1: Arrive in Portland; visit Waterfront Park; dinner and barhopping
• Day 2: Enjoy Voodoo Doughnuts and other quintessential Portland sightseeing (Powell’s Books, Nike Museum, and a coffee tour)
• Day 3: Drive to Cannon Beach and Pacific City for beach time and shopping; camping in Beverly Beach State Park
• Day 4: Short hikes and sand dune ATV-ing in small towns along the Oregon Coast; camping near Port Orford
• Day 5: Longer hike up Mt. Humbug near Gold Beach; camping near Crescent City
• Day 6: Explore Redwood Forest National and State parks; dinner at a brewery before staying at an Airbnb in Westport, CA
• Day 7: Napa winery tours and camping in Marin
• Day 8: Sightseeing in San Francisco (e.g., Fisherman’s Wharf); park and brewery visits
• Day 9: Short hike up Twin Peaks; more park visits and brewery visits, and barhopping in San Francisco
• Day 10: Breakfast in SF and fly home

The itinerary perfectly included a diverse range of activities that met each member of the trip where they were. Short hikes and longer hikes were balanced throughout the trip to avoid fatigue, and destinations were staged throughout the week to ensure we were achieving a great mix of outdoor adventure and urban exploration.

As the experienced outdoors-person of the group, Nate took the lead on outdoor logistics such as booking campsites and selecting camping gear so that Spencer and Aaron could focus on enjoying themselves, and challenging themselves, in the outdoors. Nate also anticipated, and proactively mitigated, potential obstacles associated with the group’s level of experience in the outdoors – for example, breaking up five nights of camping with one night in an Airbnb, so we could get a great night’s sleep and a warm shower.

The trip was a rousing success, and our group proved that a complicated outdoor trip need not only be pursued by expert campers. Working together, with Nate at the helm, we created and executed a plan that took us off the beaten path, showed us the very best of a new place, and played to the capabilities and desires of the entire group. By the time our trip wrapped up in San Francisco, we were already planning our next road trip – a sure sign that we had shared an unforgettable adventure.