Four Winds Westward Ho is a 97-year-old residential summer camp located on Orcas Island, WA. Campers aged 9-15 spend four weeks living in groups, learning new skills, making new friends, and taking care of each other, away from electronics and at a slowed-down pace that we believe is great for kids. Fostering campers’ connection to the natural world around them, giving them opportunities to do a hard thing and succeed, and instilling in them a sense of self-sufficiency are critical parts of our mission, and to that end each camper goes on an out-of-camp wilderness trip every summer. Trip groups range from 4 to 14 campers, and lengths range from 1 to 5 nights. Campers travel via canoe, kayak, sailboat, and on foot – water-based trips depart right from our dock! Six ‘trippers’ lead these trips, and the entire program is overseen and managed by a Head of Trips.

The Head of Trips supports the camp program by planning, supervising, executing, and evaluating a safe, challenging, and fun out-of-camp trip program. The Head of Trips helps to coordinate and carry out trip staff training (including leading a three-night training trip); supports, manages, and evaluates the performance of a staff of 6 trip leaders; ensures that boats, gear, food, and overall scheduling of trips are in order. They work closely with the Kitchen Manager, Boatwright, and Summer Leadership Team to ensure smooth transitions between in-camp and out-of-camp time. This position reports directly to the Camp Executive Director. They plan and execute the 15-day Trip Leader training period prior to camp, and are a part of the core summer leadership team. The Trip Coordinator may or may not lead trips themselves.

Preferred qualifications:
– Availability for the whole duration of the contract (if you have a previous engagement that is 72 hours or shorter, let’s talk!)
– Wilderness First Responder Certification
– Lifeguard Certification (or the ability to get it)
– Demonstrated proficiency in coastal marine navigation
– Experience reading weather, tides, currents, and human factors in making on-water risk management decisions
– Deep familiarity with coastal sea kayaking/canoeing, including wet exits and rescues
– Experience coordinating multi-day trip logistics
– Ability to manage a diverse team of adults
– Significant experience leading peers and groups in the outdoors
– Strong communication, decision-making, logistical, and organizational skills
– Demonstrated love for working with children, and the patience and sense of humor to match
– Ability to accept and give constructive criticism
– Ability to remain calm, think clearly and act quickly in case of an emergency
– Comfortable and effective in public speaking
– Ability to serve as as an ambassador for the organization with the public and with land managers
– A willingness to jump in and help, even if it’s a bit outside of your job description

Tagged as: Water Skills


- Familiarity with Puget Sound waterways
- Experience managing wilderness evacuations
- Small-boat sailing experience
- Rudimentary boat maintenance experience
- Multi-day backpacking expedition experience

Required Skills:

- trip leading experience
- very comfortable with water
- willing to get WFA and Lifeguard certified
- love working with children
- team player!

About Four Winds * Westward Ho

Four Winds Westward Ho is a 97-year-old residential camp located on Orcas Island. We run two month-long sessions with campers aged 9 -15.

Application Instructions

Reach out to [email protected] with any questions or submit an application on our website: https://fourwinds.campintouch.com/ui/forms/application/staff/App?_ga=2.188474472.1987770801.1715302353-111756297.1676662175