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Penobscot Bay & Islands Sailing expeditions explore the rugged shoreline, intricate rivers and granite, spruce-studded islands of the eastern seaboard’s wildest region. This journey is an opportunity for those seeking a fresh challenge in a unique marine environment and an intense team setting.
Our 30-foot open sailboat serves as both home and classroom. In a phased teaching progression, instructors will introduce beginning, intermediate and advanced skills in chart and compass navigation, small boat seamanship, weather observation, and anchoring. Regular group discussions allow for reflection on each day’s progress, and ensure that leadership and on-board responsibilities are shared so that every crew member is integral to planning the next day. Through living and working closely together, students learn far more than seamanship. The habits learned and strengthened through this sailing expedition will serve students for life, and for whatever challenge is next.
Your course will begin at the Hurricane Island Outward Bound School’s Sea Program base camp located at Wheeler Bay in Spruce Head, Maine. Here you will get your first introduction to your boat, essential briefings on emergency procedures, and then you will cast off lines and begin your adventure on the water. All courses are “expedition-based,” which means that you will leave the base camp on the first or second day of your course and not return to it until the end of your course. You will row or sail nearly every day, developing skills as you travel along your planned route. On board you will carry all you need: stoves, shelters, food and water, etc. Bathing occurs daily with an ocean swim. No boating experience is necessary. We will teach you everything you need to know: sail handling, steering, anchoring, navigating using chart and compass, and living comfortably aboard a small open boat. Arriving physically fit will enhance your experience and ability to do well on the course and ultimately allow you to take full advantage of the expedition.
The 30-foot open sailboat is your home and classroom. These seaworthy boats are rigged to take full advantage of the power of Maine coastal winds, and when the winds do not cooperate, the boats can be rowed by two or four people pulling on oars. At night the boat will be configured as a sleeping platform and you and your watch mates will take turns at anchor watch under brilliant night skies. Underway, you will learn to set your sails properly for sailing at different angles to the wind, and to anticipate and respond to changes in weather. As you practice rowing, you will discover that by coordinating all of the rower’s movements so that the oars splash as one, you halve the effort it takes to travel on windless days. You will learn to navigate using a chart and compass across open water and among the bold granite islands, concentrating on the environment around you.
During your course you may have the opportunity to do some rock climbing on one of this area’s many granite cliffs or on our ropes course at the Outward Bound basecamp. You will learn to use climbing equipment, tie knots, climb and belay each other, while instructors provide overall supervision of the site. Climbing gives you a chance to practice your balance, coordination, and flexibility as well as the group’s ability to trust and encourage each other.
It is important to keep in mind that being able to climb is dependent on a variety of factors such as weather, course route/length, and staffing availability. We intend to have this be an element of your course, but it is not guaranteed.
Service projects are often incorporated into Outward Bound courses through coordination with local land managers, conservation groups, government agencies or social service agencies. While in the wilderness, students are encouraged to practice service to the environment and their team by sharing responsibilities and following Recreate Responsibly ethics throughout the expedition.
The solo experience is a standard element of Outward Bound courses. With sufficient food and equipment, you will set up camp at a site on your own. The solo will last anywhere from a few hours to a few days, depending on the length of your course. Your solo site is chosen to offer as much solitude as possible, yet be within hearing distance of other group members. You will not travel during this time alone, and your instructors will check on you occasionally. The solitude and break from the fast pace of your expedition allows for rest and personal reflection, which is necessary to make the most of your experience.
Our courses end with a Personal Challenge Event, an individual final physical push. These events typically take the form of a running and/or swimming activity, though may include another element that you learned during your course. This event is a chance to finish your Outward Bound Experience with a true personal challenge where you can own all of your decisions and efforts in contrast to the time you have spent operating within an expedition team.
Open Boat Sailing Skills
Rock Climbing (dependent on various factors)
Expedition Skills
Group Dynamics
The essential goal of any Outward Bound course is for the students to learn autonomy. Our expedition curriculum supports this happening in a progressive way.
During the first third of a course (a phase called “training expedition”), the instructors are very present in the group. They teach outdoor skills, the technical aspects of the activities and guide the students as they form a team.
In the middle third of the course (what we call the “main expedition”), the instructors take a step back so students may step forward. Students begin to teach what they’ve already learned to each other, and experiment with applying basic skills to bigger challenges. The instructors continue to coach and support as the students practice leadership roles. When the group meets a particular situation, environment or activity they haven’t learned about before, the instructors jump back in and teach. Each time this happens, the group reaches competency more quickly.
By the last third of the course (the “final expedition”), students are the stars of the show. They are applying what they know, leading each other, setting goals, and solving problems collaboratively. The instructors are close by and ready to step back in to prevent a safety issue from occurring but will let students find their own resiliency when they make mistakes, and ensure they feel the full spotlight of success when they meet their goals.
Your course area along the coast of Maine, with its intricate and indented shoreline, is a unique segment of the North Atlantic seaboard. It is renowned among sailors for its picturesque beauty, iconic lighthouses, abundant bays and harbors, rocky islands, and quiet coves. Our cruising area covers nearly 200 miles of the Maine coast, with countless rivers, bays, and islands to explore. The rocky, spruce-covered islands are the summits of a prehistoric mountain range; many generations of inhabitants have made their livelihoods here. Evidence left behind on the islands reveals the historic presence of indigenous Abenaki camps, pre-colonial fishing communities, post-colonial timber and farming operations, and early 20th-century granite quarries. Cold, nutrient-rich waters flow from the Canadian Maritimes and make the Gulf of Maine home to a wide range of sea birds, seals, porpoises, and whales.
On your HIOBS program, you will learn four important Outward Bound Core Values:
Some of the most important lessons you take home are learning about yourself and your community while acquiring backcountry skills and having an adventure. As you will be traveling through wild places on your expedition, you’ll also learn to protect and appreciate the unique, unspoiled environments through which you travel.
Our courses for 13- to 14-year-olds are designed to introduce young teens to Outward Bound. Supportive instructors teach the skills of wilderness travel, and guide the formation of the group into an expedition team. As the students’ abilities grow, the instructors intentionally and progressively challenge them to take on more responsibilities, try out more leadership roles, and develop a heightened sense of self and purpose. Under the close supervision of caring instructors, students are permitted to share ideas, experiment, triumph…and sometimes fail. While safety is conscientiously maintained, students may feel moments of frustration, disappointment, cold, wet and tired. At such times, we coach young teens to review their choices, weigh the results, decide what changes to make, and try again. We find this teaches decision making, responsibility and resiliency, and ensures that the group knows that all successes are truly theirs! Students return readier to fully participate and positively engage at home, at school, on teams, and in their communities.
You need to be physically fit, and motivated to live, learn and work together within your expedition team. You will need to be ready to work and live with crew mates with different views and values from all different parts of the country and world. No previous wilderness travel or camping experience is necessary—all travel and leadership skills are taught from the beginning, and each day of the expedition builds on the previous one.
Please pay attention to the due dates listed in your Welcome Email. If due dates are not met, you risk losing your position on course - our policies on cancellations and deadlines are outlined in the Admissions Handbook.
If you are having trouble getting the information together, or have any questions at all, please contact your Course Advisor immediately so we can help you.
Payment of tuition is due 90 days before course start, or within 5 days of enrollment if you are within the 90-day window. Payment information and policies can be found here.
You are welcome to bring extras of the items marked with a plus (+) sign. Where a range of quantities is indicated, e.g., “1-2” bring the smaller quantity if you are on a one-week course, and the larger quantity if your course is 10 days or longer. There are multiple brand name options available at varying prices. The clothing and equipment on this list is widely available in many places. Specialty outdoor stores like L.L.Bean, REI, Campmorand Eastern Mountain Sportswill have a range of appropriate items to choose from. Discount retailers, like Sierra Trading Postand the REI Garage often have good prices on name-brand gear and clothing. You may also locate many first- quality clothing and equipment items at military surplus stores and area consignment stores and thrift stores, such as Goodwilland The Salvation Army.
The HIOBS website has some great items. A complete collection of HIOBS-recommended-for-course items can be found HERE. Please contact your course advisor for suggestions.
Packing several light layers rather than fewer heavier layers allows you more flexibility as the weather and workloads change. Inner layers should fit closely, middle layers should fit loosely and outer layers should be just a little bit baggy. When shopping or packing, it is a good idea to try on your layers together.
Before your expedition, your instructors will check your gear; they will assess your clothing with the actual route and the anticipated weather in mind. Items you don’t take on expedition will be stored safely at base. We suggest leaving the tags on any items you purchase in case you don’t actually pack them for expedition, but please note that you should check with each store to see what their return policies are. If there are items that you would like to bring but which are not mentioned on this list, feel free to call and ask your course advisor at 855-802-0307.
Tick- and mosquito-borne diseases are an increasing risk of traveling in the wild regions of the Americas, including our course areas in Maine, New Hampshire, Florida, the Bahamas, and Costa Rica. Fortunately, there are prevention steps that are very effective and, in most cases, treatment is relatively simple and recovery complete, so long as the diagnosis is made early. Students and their families should educate themselves on the risks, prevention measures, and signs and symptoms of tick-borne illnesses.
Since prevention is always better than treatment, we STRONGLY recommend pre-treating your footwear, long pants, long-sleeve shirts, jackets and hats with a chemical barrier containing permethrin, at least two days before traveling to your course. Applied correctly and allowed to dry before wearing, the treatment remains effective for up to a month. For even longer-lasting protection, you can either purchase clothing with permethrin embedded within it, or send your clothes to Insect Shield®, who will treat them and ship them back to you, ready for your course. Use the Coupon Code “HIOBS” to receive a 15% discount on both clothing and treatment services at this website (please note that you need to use the coupon separately for products/ service).
Permethrin spray is readily available at many retailers, including Dick's Sporting Goods, Campmor, and Walgreen's.
For more information, please download our Vector-Borne Disease General Fact Sheet.
Summer in Maine is often warm and sunny, but cold fronts are common and these bring wind and rain. Out on the water, the air stays cool and moist so warm, quick drying clothing is essential. The sun can be intense making sun protection (sun screen & clothing) very important. Temperatures at night can drop to the 40s and even lower in May and September. Daytime temperatures range from the 50s to the 80s.
These are NOT required items. Please only buy them if you plan to use them outside of your course.
Please note that Outward Bound provides all other equipment, including (but not limited to):
Please review the times and locations for Course Start and Course End as you plan your travel to and from course.
Do not purchase any travel tickets until your Course Advisor has given the "go-ahead" to book travel for your course. This message will be in either your Cleared to Participate email or a separate message confirming the course is cleared to book travel.
Travel details (flights and drop-offs) are due to your Course Advisor 10 days before your course start date. This helps our airport shuttle teams get organized and ensures we have enough seats available for all students needing a ride. You will receive a Travel Form link from your course advisor. Please complete this form, even if you are being dropped off by car.
Students flying without an adult/guardian may need to bring an ID when traveling to and/or from course. If you need to obtain a non-driver ID card, please see your local Department of Motor Vehicles office. For more information, go to www.dmv.org/id-cards.php.
Arrival Location: Portland International Jetport (PWM), 1001 Westbrook St, Portland, ME 04102
Students must arrive BY 1:30PM. Our HIOBS staff and shuttle van will meet students at the airport. Once you get there, look for Hurricane Island Outward Bound School staff members – they will be wearing HIOBS apparel, and will have a sign or clipboard with the HIOBS logo (see below). Students may gather in the foyer between the escalator and baggage claim area of the airport starting around 1:00 pm. If you don't see HIOBS staff when you arrive, please sit tight and keep your eyes open for them. They are often moving around greeting students, helping gather baggage and answering questions. Students should check in as soon as possible with the HIOBS staff member, and then wait in one of the seating areas until we have accounted for everyone.
If you are arriving early, we suggest purchasing food before going to baggage claim. There are very limited places to eat once you've exited security.
If you think it makes more sense for you to arrive directly at the Outward Bound base, please contact your Course Advisor to discuss alternate arrangements.
Departure Location: Portland International Jetport (PWM), 1001 Westbrook St, Portland, ME 04102
Please do not schedule a departing flight earlier than 1:30 PM. Our staff will assisting students in checking in by around 12:30pm.
If you are being picked up at the Jetport, whoever is picking up should park in the hourly parking and then come to the Departures area. Our staff will be in the check-in/ departure area of the airport assisting those students who are traveling by air with their check-ins by around 12:30pm. Please check in with HIOBS staff before departing.
Airfare, related travel costs, and non-refundable tuition payments are expensive. Insurance to protect your trip and course is not required but strongly recommended. If you choose not to purchase insurance and cancel your course or leave your course early you will be held to the terms of the Cancellation Policy (See your Admissions Handbook).
Outward Bound offers an option for insuring these costs from the third-party provider InsureMyTrip through its Academic Explorer Program. This program has coverage options that include your travel costs and the non-refundable tuition costs. A link to that program’s insurance coverage options is below. Alternatively, you may choose to purchase trip related insurance through a different insurance provider. In either case, the amount and type of coverage you choose is your responsibility and must be discussed directly with the provider.
Learn more about INSUREMYTRIP here
You may also want to consider insurance for the cost of Emergency Evacuation. Health insurance often does not cover the cost of emergency evacuation by air or other means and these costs can be very expensive. HIOBS will not be financially responsible for these costs in the event that your student requires evacuation. The Academic Explorer Program offered through InsureMyTrip does not offer coverage for emergency evacuation. You will need to purchase that coverage from a different insurance provider. Outward Bound makes no representations or warranties about these insurance options or how they handle claims.
If your course contains an international component (Costa Rica or Bahamas), please make sure to read about the "On Call" International Insurance provided by HIOBS. You can find this information in the Course Overview tab.
PARENTS of students ages 13-16 who will be flying unaccompanied—please read carefully:
Recently, the airline industry has adopted stricter guidelines for children ages 16 and under flying unaccompanied by an adult. Each carrier has different rules about who must fly with Unaccompanied Minor (UM) status, depending on the minor’s age, the flight route and stops. This UM status will require an additional fee of $100-$150+, and may require additional forms. If your child is under 16 and is traveling without an adult, you MUST check to see if the airline you have chosen will designate them as an Unaccompanied Minor, and inform us of his/her status. This allows us to ensure we have sufficient staff at the airport to meet your child upon arrival, and/or accompany them until they board their flight after Course End. We cannot ensure this level of staff support without advance notice.
Your airline will ask for a contact name and phone number as the pickup person. Please ask your Course Advisor for the details of this person.
NOTE: The airline may not apply this status when you originally book the travel, but may choose to do so at a later date. They may require you to upgrade to UM status (and pay the additional fee) when your child checks in with the airlines to fly to Course Start. WE STILL NEED TO KNOW – please call us if this happens. Some airlines may require students 13-15 years old to be designated as Unaccompanied Minors when they check in at the airport for departure at Course End – even if they weren’t designated as an UM on the originating flight, so please make sure to ask your airline about their policies at the time of booking.
If you encounter changes to your travel plans after you have submitted your Travel Form, please contact your Course Advisor to update them about the change.
If you encounter problems with your travel plans that will delay your arrival, please refer to the on-call number(s) in the "Final Details" email you received (will receive) 2-days before course start. Keep in mind that your course advisor may not be in the office on your travel day and will not be able to assist you with travel delays. So it is important that you contact the number noted in the Final Details email to notify your program team of the delay.
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