If you have any questions about our sailing school and our motivation for starting these sail training expeditions, please don’t hesitate to contact us. In the meantime, our frequently asked questions might help answer some of your questions.

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Ben & Teresa Carey

Who are the Instructors?
We (Ben and Teresa Carey) are both USCG Licensed Captains (200 ton & 100 ton) and experienced educators. We have sailed a combined 80,000 nautical miles on over 50 different vessels ranging from 16’to 180′, sail and power. We’ve delivered boats to and from the Caribbean, been across the Atlantic, circumnavigated Newfoundland and lived aboard during chilly New England winters! We both have worked on many sail training vessels in positions from dishwasher or deckhand to mate, engineer, chief medical officer or captain and we are committed to delivering a safe, fun, and educational passage. We have two decades of experience in sail training with advanced and novice crew. We’re both Outward Bound instructors, and former highschool teachers! Ben has worked on a variety of commercial power vessels including landing crafts, tugboats and supply boats.

We’re not just sailors trying to make a living doing what we love — we are educators, who love to sail. We love teaching topics such as basic sail theory, weather, technology, voyage planning, first aid at sea, engine basics, traditional navigation & triangulation, VHF protocol, RADAR, anchoring, communication and leadership, bridge resource management,etc.

We are regular contributors to SAIL and Cruising World Magazines, and Teresa is a sought after speaker — watch Teresa’s TEDx talk here.  You can read more about us at our blog sailingsimplicity.com and watch the trailer for our  film One Simple Question about a sailing adventure in search of an iceberg.

Ocassionally we cannot instruct a course and will hire a co-instructor. We always hire professional sailors with experience in sail-training. So far we have been able to hire other USCG licensed master’s with at least 4 years of professional sail-training experience.

Who Are My Shipmates?
In addition to instructors, on coastal there may be as many as five adult students aboard the boat selected via an application and phone process. On offshore passages, we limit  it to four students.

Night passages and hands on learning are a regular part of our courses.

Night passages and hands on learning are a regular part of our courses.

Can I Contact a Reference?
Yes! You can check out our testimonials first, and if you would like to speak with former students, please let us know. In the meantime, watch a video testimonial of a recent sail training expedition.

Can I Become Crew (Not a Trainee) on an Expedition?
Occasionally we do need assistance on a yacht delivery or sail-training expedition. In those circumstances, we hire professional sailors with experience. You are welcome to email us your resume for consideration. However, we are not hiring regular employees. People often ask us if they can be volunteer crew to gain experience. Our sail-training programs are designed to offer both novice and knowledgeable, skilled sailors enough practical experience to take their sailing to the next level. Because our yacht delivery and sail-training programs are professional expeditions, all passengers are paying trainees, and all crew are paid experienced professionals. We cannot make exceptions.

What Am I Expected to Do?
You’ll take part in all the responsibilities of keeping a cruising vessel running. Cooking meals, cleaning the head, taking the helm, changing sails, weighing anchor, navigating, etc. Everyone will be assigned a daily role from Captain to Mess Mate (aka dishwasher). The duties will rotate daily. So, don’t worry, if your stuck washing dishes on the first day, you’ll have your chance to captain the vessel soon! The only thing we expect you to do everyday is have fun, and learn.

Sailing School - custom coastal and offshore expeditions. Morse Alpha.

We place a lot of value on traditional navigation skills

 What Will I Learn?
We have created a curriculum that will develop your leadership, crisis management, communication, and teamwork skills while simultaneously honing your technical sailing and seamanship skills. Because we are limiting the voyage to only 4 or 5 students, each program is tailored to meet the needs and goals of the students. We will assess your skill level and build from there. You can download our list of technical training topics that we could cover. Just like a typical sailor’s day, our curriculum will be influenced by the weather and circumstances we are given. We will take opportunities as we see them, with the goal that we cover our focused curriculum. Your program will include topics and drills such as man overboard, traditional and electronic navigation, night travel, watch keeping, engine maintenance, sail trim, fog procedures, and more. And if there is something you are eager to learn or practice or perfect, we will work on that too… like docking for instance!

Can I Bring My Non-sailing Spouse?
Absolutely! Our program is great for couples with varying levels that are seeking to develop trust, reliability, communication, and teamwork skills. No single person will be designated full time cook, and no single person will take every stormy watch. We believe that anyone (of average physical condition) can, and should, be prepared to tackle any job on the boat and we are excited to train you with this egalitarian approach.

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We also love to have fun!

What is a Typical Day Like?
There is no typical day at sea. However, we try to start each day with Morning Muster, facilitated by the Captain of the Day. This daily routine is a time when the entire crew will gather together to cover daily topics and check-in. We have found Morning Muster to be a time that the crew looks forward to, and many will carry the tradition on after the program concludes. Throughout the day we will have lessons and practice drills such as anchoring, triangulating, man overboard, storm tactics, etc. These lessons will depend on the weather and if we are day sailing or cruising overnight. We will make best use of the circumstances that nature provides, and create scenarios for practice when necessary. If we are day sailing, we will anchor in the evening and the chef for the day will prepare a delicious meal. We often conclude the day with a lesson or review of things we learned and experiences had.

Preparing for your Expedition:

If you have a question and don’t find an answer below, feel free to email Teresa! We will try to keep this updated, but if you find a link no longer works – let us know.

Q: Do I need to purchase a lot of gear for the expedition?
A: Yes, and no. Most everything on the packing list you should already own. There may be a few exceptions. You will need marine foul weather gear, a PFD, and a good pair of sunglasses. If you continue sailing, then all of these items will become essentials and will get a lot of use. Everything else on the list are things that are likely already in your closet: shorts, t-shirts, jacket, etc.

Q: Where do I purchase gear for the expedition?
A:
Great stores for marine gear are Defender Marine, Hamilton Marine, and West Marine. To purchase fleece or wool pants, a sun shirt, or other items look in Goodwill, Old Navy, REI, or Mountain Equipment Co-Op.

Q: What type of PFD should I bring?
A: Everyone is required to wear a PFD at all times while underway. We require a Type V, auto inflating PFD with a harness. Look for “offshore” in the description, as that often means it includes a harness. If you would like to wear a different PFD, please ask us first. Your PFD should have an updated inflation cartridge, which should be checked regularly. Here are a few PFD options:
WEST MARINE Offshore Automatic Inflatable Life Vest with Harness $229.00- Teresa’s Pick!
SPINLOCK Automatic Inflatable Deckvest™ with Harness $369.00

Q: Can I bring a CO2 cartridge (for my PFD) on the airplane?
A: I haven’t had any trouble bringing a CO2 cartridge on airplanes in my checked baggage. I’ve heard that it is even easier if it is one that hasn’t yet been pierced, meaning it hasn’t yet been installed in the PFD. However, I do not know the official “rules.” If you find out, please let me know! If you could purchase a cartridge locally so you do not have to travel with it. If you are sailing out of Rockland, ME please call Hamilton Marine (207) 594-8181 to purchase your cartridge. Have them hold it under Teresa and Ben Carey. Then let us know you’ve purchased one, and I will pick it up before your course.

Q: What type of foul weather gear do I need?
A:
We recommend bringing marine “foulies” foul weather gear. Most terrestrial gear does not hold up in the marine environment. Gill, West Marine, and Helly Hansen are great brands. Look for “ocean” and “offshore” as keywords in the description. Some “coastal” foulies, if they are heavy duty, will also work. Get foulies with a hood and Velcro or snap cuffs. Foulie pants should be bib style. Most lightweight, some coastal, or dinghy gear will not suffice. Remember, you aren’t just keeping the rain out, you are also keeping out the salt spray and pounding waves. Fishing foulies will keep you dry, but are not recommended in hot environments, as they do not breathe and most people get sweaty and uncomfortable. However, in northern climates, they work well. Many great brands can be purchased at West Marine.
West Marine Third Reef Jacket $189.00
West Marine Third Reef Bibs $169.00
Gill OS2 Offshore Jacket $325.00
Gill OS2 Offshore Bibs $225.00

Q: What about boots?
A:
Rubber rain boots are needed in Maine or other northern climate expeditions. You will not need boots in the tropics!
Gill Tall Yachting Boots $85.00
Gill Short Cruising Boots $65.00

Q: Do I need to bring food?
A:
All the food is provided. We pack enough for a variety of meals and snacks. We plan for 3 meals each day, one daily snack, and an occasional dessert. In addition, we keep a snack locker full. You are welcome to help yourself to anything whenever you feel hungry. If you have allergies or dietary needs, please indicate so in your application. So far we have been able to accommodate every dietary need.

Q: What is the sailing itinerary?
A:
On our coastal expeditions in Maine and the Caribbean, there is no planned itinerary. The weather has a huge influence on where we will be able to go. Additionally, the latter half of the expedition is planned by the participants, so you and your shipmates will determine your anchorages. Unless there is extreme weather, we plan to sail every day – rain or shine. We also plan at least one night sail, and a possible overnight (depending on the expedition you’ve selected). For the passage expeditions, we typically have a few coastal days before or after make the offshore passage.

Q: What if I get injured or have a medical emergency?
A: Both Ben and Teresa have medical training and certifications and are prepared to deal with most medical emergencies at sea. If it is beyond our abilities and resources, we will take you to the nearest medical facility. In extreme circumstances, we may call for emergency support.

Q: Could an expedition get cancelled, re-routed, or changed?
A: Anything is possible! We’ve been conducting expeditions for many years, and so far all of them have started and ended on time! However, there is always the possibility of lengthy delays due to conditions beyond our control. We are prepared for this as we schedule our passages with a few extra days of flexibility to be adaptable to the weather. We haven’t had to cancel or delay an expedition yet but if extreme weather were predicted then we will consider it. You may want to purchase travel insurance for the unlikely event that this happens. Here are two options for travel/trip cancellation insurance. If you find another great one, let us know so we can improve our list of suggestions!
http://www.csatravelprotection.com/
http://www.travelguard.com/

Q: What if I need to leave the expedition early or my plans change?
A:
If you leave the expedition early due to a medical emergency, need to return home, etc. or if you are registered for an expedition and are unable to attend, please refer to our cancellation policy in the application packet we send you. You may consider travel/trip cancellation insurance for some of these situations. See above for suggestions.

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