Our Instructors

Most of the instructors who will be joining you in your class learned to sail at Courageous, just like you. They, too, come from all different neighborhoods in and around Boston and, by now, know the harbor like the backs of their hands! Other instructors come to Courageous from all over the country and even from all over the world. We've had instructors join us from Ireland, Scotland, and even Italy! Many of our older instructors have also sailed boats in the Caribbean, Mexico, off the coast of Cananda, and in the Mediterranean, to name a few.Your senior instructors also have certifications from places like US Sailing, NOLS, SOLO, RYA, and even the US Coast Guard—they really know their stuff! These instructors are chosen to ensure that every student will learn new things, stay safe, and have a great experience at Courageous Sailing!

Interested in joining the team?

Each year, Courageous hires over 100 seasonal staff and instructors. The Courageous instruction team is enthusiastic, energetic and diverse. A few grew up in the program. Several race competitively in the local high school and national collegiate circuits. Others are seasoned racers and cruisers who have sailed across the country and all over the world. Many are students, teachers and other professionals looking to take a breather from the real world and spend a summer outside, on the water, doing what they love. While each brings their own experiences and reasons for coming, what unites them is a shared a passion for sailing and a commitment to expanding the horizons of the kids they work with.

If you've never instructed but want to get involved, consider boathouse staff openings, volunteer opportunities, or, if you're a sailor between the ages of 15 and 18 who thinks they might like teaching, check out our Instructor-in-Training program. If you love the water, kids, sailing and teaching, check out openings for instructors.
Find out more about available positions and apply today.



1-to-3: One of the best instructor-to-student ratios in the business.

Step 1 Sailing 101 or Swim, Sail, Science: Youth can expect to sail with two other children and an instructor in a boat. No experience required!

Step 2: Beginning Sailing: Youth can expect to sail with two other children and an instructor in a boat.

Step 3: Intermediate Sailing: Youth can expect to sail with two other sailors of their level, monitored by instructors in a safety launch. More experienced youth may sail alone in a smaller sailboat, like a Laser 4.7, monitored very closely by instructors in safety launches.

Step 4: Advanced Sailing - Racing & Cruising: For cruising, youth will sail with three to four other sailors of their level, monitored by senior instructors on board the cruising boats. For racing, youth will sail on their own or with one or two other sailors of their level aboard 420s, monitored by instructors in a safety launch.




Courageous Mainsail Partners


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