CB32 Program Banner

Middle School

Penobscot Bay & Islands â€“ Sail

Set off on a 9-day sailing adventure along Maine’s wild coast, where you’ll live aboard a 30-foot open sailboat, explore hidden islands, build skills, and work in a team setting with your crew.

Schedule a Call
See Available Dates & Apply

Maine

The image shows a sailboat on the water with several people on board. The boat has a large white sail that is full of wind. The people on the boat appear to be enjoying a day of sailing. The sky is blue and the water is calm. The overall scene is peaceful and serene.
CB20 Course Overview

About This Course

Activity

  • 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

3 sessions are available for this course

Chat with the Customer Success Team
A group of people are gathered on a small sailboat, working together to raise the sail. The boat is on the water, with land visible in the background. The sky is partly cloudy. The people appear to be enjoying a sunny day out on the water, engaged in a sailing activity.

What You'll Learn

On Outward Bound courses designed for middle schoolers, you’ll do exciting things with new friends, build confidence, and discover you’re capable of more than you know! You’ll have fun, work on your willpower and crush right-sized challenges – together.

Three young women are standing close together, likely on a rocky terrain, possibly getting ready for or just finishing rock climbing. They are all wearing helmets and harnesses, indicating their involvement in climbing activities. The woman on the left is wearing sunglasses and a blue t-shirt, the one in the center has a white t-shirt, and the woman on the right is wearing a red helmet and a plaid shirt. Ropes are visible, further suggesting they are equipped for climbing.

What You'll Do

With the sailboat as your home and classroom, learn essential seamanship skills like chart and compass navigation, anchoring, weather observation, and boat handling. You’ll also help plan routes, cook meals, and share leadership and onboard responsibilities with your crew.

The photo shows a group of young people on a boat, possibly sailing. They are gathered around a map, seemingly navigating or planning their route. The individuals are wearing life jackets, suggesting a focus on safety. The background includes water and some land, indicating they are likely on a coastal or lake environment. The overall scene conveys a sense of teamwork and adventure.

Where You'll Be

Sail nearly 200 miles of Maine’s rugged coast, where rocky, spruce-covered islands rise from the sea and quiet coves hide rich history and wildlife. Explore rivers and bays, spot seabirds, seals, and porpoises, and experience one of the most iconic coastlines in the world.

A woman wearing a hat, sunglasses, and a red long-sleeved shirt is sitting in a small boat on the water. She is holding a black paddle with both hands and looking off to the side. She is also wearing a life vest. There is a water bottle next to her. The boat appears to be under a sail.

Why It Matters

You belong here! Outward Bound is a unique place to try new things, make friends, and discover your strengths. Building community – and new skills – through adventure is what we’re all about. Find your crew here!

/

CB11 Scrolling Bullets

Confidence Starts Here

What if you learned how to face obstacles head-on while feeling brave, included, and proud of who you are?

Educational Approach

One-Week Courses for Middle School

Try exciting things and practice new ways of connecting with your group. You’ll take on challenges, weigh healthy risks and work together with your crew to find success! Are you ready for adventure? Let’s go!

Bravery Meets Belonging

Uncover your own bravery with support from your crew. Meet challenges designed to activate your strengths, develop persistence, and show you what you’re made of—even when things get tough.

Skills for Life

You’ll practice key skills like communication, taking initiative, and problem-solving with purpose. You’ll be given space to make choices – and take responsibility for them. Through trial and error, learn how to face obstacles head-on—growing more capable with every step.

Stronger Together

You won’t go it alone—crew is everything. You’ll explore common ground with your crew while also learning how to acknowledge each other’s uniqueness in a group where every voice matters.  You will learn how to face challenges as a supportive team, forging strong friendships.

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.

9-Day Course

+ -
Day 1 Travel to course, welcome, equipment issue and check, introduction to Maine coast
Day 2-4 Sailing expedition
Day 5 Rock climbing (weather-dependent), Solo
Day 6-7 Final expedition
Day 8 Return to base camp, Personal Challenge Event, equipment clean-up and de-issue
Day 9 Course graduation, depart for airport
CB27 Pull Quotes

I will never forget the amazing memories I have made over the past week. I have made some lifelong friends on the Maine waters, and the awe-inspiring marine life in Maine has made me deeply appreciate the natural beauty of Earth, which we often overlook…This experience will stick with me for the rest of my life.

Francis

This course was a perfect mix of challenge, friendship, teamwork, and strategy.

Will

During this course, I’ve learned a tremendous amount of things. I’ve made lifelong friends, learned to sail, tied so many new knots, rowed in sync, always tried to have a positive attitude/mindset, and challenged myself in healthy and positive ways. There are so many more things I have learned…that list would be at least a few pages!

Isabella

CB17 FAQs

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.

Sign Up for Updates from Outward Bound

+ -