About This Course
Activity
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Sailing
Setting & Location
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Coastal -
Course Start Location: Portland, Maine -
Course End Location: Portland, Maine
Session Details
2 sessions are available for this course
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Veterans Courses
What if you can find familiar connections in unfamiliar places?
Lead in New Ways
Tap into familiar leadership skills and learn new ways to engage with your crew to meet and navigate through unique challenges.
Connections That Last
Build connections that outlast the adventure as you and your crew learn to recognize each other’s strengths and celebrate success together.
Confidence Beyond the Uniform
Leaving the military can feel disorienting. Our Veterans courses offer a supportive crew and purposeful challenge—so you can reset, refocus, and return home with renewed confidence.
Life on Course
Experience life on the Maine coast where rugged islands, shared leadership, and hands-on seamanship create a mission-driven, team-focused journey for veterans.
Specifically designed for veterans, this expedition provides the space to live, learn, and connect as you navigate rugged shorelines, winding rivers, and spruce-covered islands aboard a 30-foot open sailboat. Each day brings hands-on lessons in seamanship, navigation, anchoring, and weather observation. You’ll share leadership, take on daily responsibilities, and reflect with your crew in a mission-driven environment built on trust and camaraderie. As you challenge yourself physically and mentally, you’ll build skills and confidence and reconnect with your strengths as you chart a course forward.
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Sample Itinerary
Here’s an example of what your course itinerary might look like. The actual plan will depend on permits, weather, group skills, and instructor evaluation.
Swipe on table below to view more.
6-Day Course
| Day 1 | Travel to course, welcome, equipment issue and check. Begin sailing expedition. |
| Day 2-4 | Sailing expedition; personal challenge event; Solo |
| Day 5 | Return to basecamp; equipment clean-up and de-issue |
| Day 6 | Depart for airport |
FAQs
I don't have a lot of outdoor experience—can I still be successful?
Absolutely. Your motivation to learn new skills and work with others is just as important as what you already know. Many of our students have never spent an extended period of time in the wilderness. From the moment you arrive, your instructors will teach you and your group the skills necessary to be safe and successful.
What gear will I need?
After enrollment, your Course Advisor will be in touch to provide you with a link to your Course Page, where you will find a list of required clothing specific to your course – including items such as footwear, clothing, and other personal equipment.
Outward Bound will provide technical gear that includes expedition items like sleeping bags, sleeping pads, tents/tarps, packs, and cooking gear.
Can I bring my phone or tablet on course?
This course is a technology-free adventure! Although you may travel to and from your course with your cell phones, iPods, tablets, and laptops, once you arrive, everything will be stored in a locked area in your luggage until course end.
Although some students are hesitant about this at first, many reflect on their experience as a well-needed break from screens and social media. It means more time to be present with nature—and your crewmates too.
What does the cost of the course cover?
The total cost includes all tuition and fees for the course. Tuition covers the cost of food, instruction, permits, technical gear, and equipment while on course. Courses going to Costa Rica and the Bahamas also include on-call international insurance (more information provided after enrollment).
Not included in this total cost are personal expenses such as clothing, health & travel insurance, airfare, and baggage fees.
Can I earn college credit from this course?
Yes! Academic credit is available for Outward Bound courses by transferring credit through our partner colleges or by arranging your own independent study. Click here for more information about receiving academic credit.
Can I use my 529 Plan or college fund to pay for this?
Thanks to Outward Bound’s partnership with Western State Colorado University, we can accept 529 College Savings Plan through their Extended Studies program, and anyone can register. You do not have to be a current Western State Colorado University student to take advantage of this opportunity. Please click here for more information about accepting 529 College Savings Plans.
What types of training do Instructors receive?
Outward Bound Instructors receive regular training in the outdoor activities and environments in which we run our courses. New Instructors receive extensive training in teaching and facilitation, risk management, judgment, decision making, conflict resolution and emergency procedures. After completing initial training, instructors work directly under experienced staff before being promoted to a Lead Instructor position. Lead Instructors receive continuing training and professional development annually.
Click here to learn more about instructor training and development on our Safety & Risk Management page.
How is safety managed on course?
Outward Bound courses take place outdoors and include activities that present risks that can be managed but not eliminated. Running our courses safely is central to our educational goals and our safety record is excellent. Our instructors not only identify and reduce risks but also teach students to assess and address hazards with preparation and care, rather than fear and avoidance. Students and their families participate in our safety systems by familiarizing students with the course description prior to the course and by filling out our application and medical forms completely. We regularly review our safety training systems with our peers and other industry experts and continually seek to create or adopt the most effective practices. Every course is equipped with the ability to get help in an emergency.
For more information, click here to visit our Safety & Risk Management page.