When you work with The Road Less Traveled, you become a part of an organization of experienced, authentic, energetic, and adventurous leaders and directors who all share a passion for developing our future generations and the incredible beauty of our world.
Experience the extraordinary lands and cultures of North America (Alaska, British Columbia, Colorado, Florida Keys, Hawaii, Maine and Puerto Rico) and places around the world (Bali, Belize, Cambodia, Costa Rica, Ecuador and the Galapagos, Greece, Iceland, Italy, Laos, Norway, Spain, Tanzania, Thailand and Vietnam).
The Road Less Traveled is a life-changing educational travel experience—an extraordinary opportunity to join with others, explore humanity, build deep relationships, and develop an appreciation for our world’s vast adventurous scenery and its people. As a Trip Leader, you'll have the opportunity to share your knowledge and love of the wilderness, service learning, and cultural awareness with bright and enthusiastic young people; work with other highly motivated, qualified, committed professionals; and experience extraordinary lands and cultures around the world. Trip Leaders are genuine, friendly, active, educated, and well-traveled. They are not just educators and counselors, they are spirited mentors. They are responsible, committed, purposeful and bold! Trip Leaders begin their summer with ten days of paid staff training, then guide and engage participants in service-learning projects, language immersion programs, backpacking, rock climbing, biking, kayaking, trekking, SCUBA diving, whitewater rafting, and more from June through August. Compensations for first year Trip Leaders begins at $65/day and includes all food, lodging and transportation from the start of staff training through the end of your final trip, a stipend towards certifications, and the opportunity to work with world-renown and expert guides. RLT is always looking for motivated people with a passion for life-changing travel to join the team!
2025 Trip Leader Hiring! The Road Less Traveled is now hiring Trip Leaders for the summer 2025 season. Apply early to ensure positions are still available!
A ten-day training is mandatory for all RLT summer staff. Check out staff training »
Windigo specializes in customized small group camping, lodging, hiking and themed tours for international clients traveling in a 15-passenger van (with a 5x8 foot cargo trailer). From the dramatic coast of Newfoundland to the stunning sunsets of Vancouver Island... Into the wild of Alaska’s frontier to the canyons of the Southwest... And not to forget the burning volcanoes of Hawaii or the ice caps of the Canadian Arctic, Windigo’s playground is massive.
Do you want to hit the open road, enjoy an adventure of a lifetime, and get paid for it? Join the dynamic team at Windigo as a Guide and travel to some of the coolest places in North America! Meet new people from different cultures and provide unforgettable experiences to grateful travelers. It's not a job opportunity, it’s a lifestyle. Guides will lead with service and share their passion for the outdoors through innovative trips that will get your international group hiking, biking, paddling, and more! Responsibilities include researching unfamiliar destinations, providing daily briefings, relaying historical, geographical and cultural information, handling group dynamics, maintaining outdoor equipment, organizing food shopping and cooking meals, and ensuring a safe and fun experience for all passengers. Compensation ranges from $125-$180/day plus tips and commission. Accommodations and most food while on tour are included, as well as access to pro deals, bonus options, and the opportunity to travel to enticing and off-the-beaten path destinations. If you are at least 23 years old (21 for Canadian applicants), have a clean driving record, an adventurous spirit, love the outdoors, and are looking for an exciting challenge, apply to join the Windigo team! The operation season runs from April to late October with contracts available for a partial or full season.
The Road Less Traveled is now hiring 
