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High School

Maine – Sail & Sea Kayak

Explore Maine’s coastal wilderness by sea kayak and sailboat as you navigate island waters, build outdoor skills, and grow through teamwork, adventure, and hands-on leadership every day.

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Maine

The image shows a group of people kayaking on a sunny day. They are paddling in a line, with colorful kayaks. In the background, there is a small island with a lighthouse and some trees. The water is calm and blue, and the sky is partly cloudy. The kayakers appear to be enjoying their time on the water.
A sunny day on the water shows a sailboat cutting through the waves. A person in a blue shirt and yellow hat stands near the mast, looking out at the horizon. Another person relaxes on the deck, enjoying the ride. The boat's sail is full, catching the wind as it glides across the water.
CB20 Course Overview

About This Course

Activity

  • The image shows a blue drawing of a kayak and a paddle on a black background. The kayak is depicted with visible seating and a rounded shape. The paddle is positioned diagonally below the kayak, suggesting a sense of readiness for paddling. The drawing style is simple, resembling a sketch, with clear lines defining the shapes of the kayak and paddle. Kayaking
  • The image shows a simple, cartoon-style drawing of a sailboat. The sailboat is depicted in blue against a black background. It has a triangular sail, a hull, and a small flag at the top of the mast. The drawing is basic, with thick lines and minimal detail, giving it a childlike or sketch-like appearance. The overall impression is that of a quick, hand-drawn illustration of a sailboat. Sailing
  • The image shows a stylized, blue-outlined graphic against a black background. Two hands are cupped together, as if holding or presenting something delicate. Above the hands, there are three leaf-like shapes, suggesting a plant or nature. The overall impression is one of care, growth, or environmental stewardship. The simplicity of the design and the use of a single color give it a clean and modern look. Service Projects

Setting & Location

  • The image shows a dark background with blue, pixelated shapes clustered in the lower-left and upper-left areas. These shapes might represent landmasses or abstract forms, with some resembling islands or coastlines. The pixelated style gives the image a retro or digital aesthetic, and the contrast between the blue and black creates a stark visual effect. Coastal
  • airplane Course Start Location: Portland, Maine
  • airplane Course End Location: Portland, Maine

Session Details

2 sessions are available for this course

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A group of people are kayaking near a small, sandy island dotted with trees under a clear blue sky. The kayakers are spread out, some closer to the island's shore and others further out in the water. The water is calm with gentle ripples, and the overall scene suggests a peaceful outdoor recreational activity.

What You’ll Learn

On Outward Bound courses for older high-schoolers, students do exciting things with new friends, focusing on having an unforgettable adventure. You’ll refine skills like teamwork, leadership, and navigation that expand beyond your time on course. Try new things, remember what you’re made of, and return revitalized and ready for what’s next.

A young woman is sailing on a sunny day. She is wearing a life vest and dark clothing. She is holding the tiller of the sailboat, looking off to the side. The boat is on the water, and the sky is clear. There is a mast and ropes visible, and the water is calm.

What You'll Do

While in a sea kayak, learn the basic skills of backcountry travel, planning, navigation, and weather observation while exploring remote islands and wild peninsulas. Then move to a 30-ft. open sailboat where you’ll sleep under the stars and build cooking and campcraft skills with your crew.

Where You'll Be

Paddle and sail along 200 miles of Maine’s intricate coastline, exploring rocky islands, quiet coves, and iconic lighthouses. Spot a wide range of sea birds, seals, porpoises, whales, and other wildlife that call the cold, nutrient-rich waters of the Gulf of Maine their home.

A group of people are gathered on a rocky shoreline near a body of water, possibly a lake or ocean. They appear to be looking at maps or documents spread out on the ground. The group consists of men and women of varying ages. The weather seems sunny, and the scene suggests an outdoor activity, perhaps related to navigation or exploration.

Why It Matters

Outward Bound courses are a great way to disrupt your routine, connect with new people and activities, and gain clarity about who you are and what you want to do next. Navigating challenges with a supportive crew gives you space to explore your strengths, recognize your contributions, and celebrate your wins.

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CB11 Scrolling Bullets

Ready For Anything

What if you learned how to develop strong communities with peers while confidently forging your own sense of self?

Educational Approach

Two-Week Courses for Ages 16-18

You and your crew will participate in unique activities, forging skills to thrive! Sounding your own voices – and considering others’ – you’ll have time to try new ways of working together in a supportive environment. Connecting in moments of harmony and productive struggle, you and your crew will get to ask yourselves big questions like: “Who am I; who are YOU; and how can we best get along?”

Us. But Better.

You and your crew will learn how to support each other’s success, boldly tackling challenges and persevering together through epic adventures! Our skilled instructors protect the time and space your need to both recognize your strengths and consider the strengths of others.

Prepare to Launch!

Whether you’re getting ready for a big life transition or you have another year or two before you turn the page into a new chapter, you will leave your Outward Bound course having practiced important life skills to help you be successful in both this adventure and the next!

Reflective Relationship Building

This is an opportunity for you and your crew to focus on being thoughtful about your actions, words, and the impact of each on other people. You’ll work together and on your own to practice new reflection skills that’ll help you make sense of the world and build dynamic relationships within your active crew, and beyond.

CB39 Table Feature

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.

15-Day Course

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Day 1 Travel to course, welcome, equipment issue and check, introduction to Maine coast
Day 2-7 Sailing expedition with a service day
Day 8 Arrive at basecamp and transition to sea kayaking
Day 9-14 Sea kayaking expedition, and Solo
Day 15 Course graduation and departure
CB27 Pull Quotes
Two people are sitting on a rocky surface, possibly a large boulder or a rocky outcrop. One person is wearing a dark hat and appears to be pointing at a map, while the other person is looking at the map. Both are dressed in casual clothing suitable for outdoor activities. The surrounding environment consists of more rocks and stones, suggesting a natural, possibly coastal or mountainous setting.

Through 5 days and 80 miles of sailing and 26 miles and 6 days of kayaking, I learned a lot about myself and the outdoors. I can do hard things & laugh all along the way!

Elise

This Outward Bound course opened my eyes to a lot of my personal goals and what makes me happy. It gave me time to reflect and think deeper into what I’m grateful for and the everyday things I take for granted.

Andrew

CB17 FAQs

FAQs

I don't have a lot of outdoor experience—can I still be successful?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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.

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