Sports · Boston
Instructor-in-Training (IIT) Program
Courageous Sailing
Paid summer job-training program for experienced youth sailors 15 and up; seven weeks of professional training (teaching theory, cruising, powerboat operation, race committee, maintenance) leading to




What to know
- Who it is for
- 15 and up (must be 15 before July 1)
- Published cost
- Paid program (participants are paid employees)
- Venue
- Pier 4, Charlestown Navy Yard, Boston, MA
- When it runs
- Jun 28, 2027 – Aug 20, 2027 · Mon, Tue, Wed, Thu, Fri · 8:30 AM – 4:00 PM · Charlestown, Pier 4
- Registration
- Opens Feb 1, 2027 — 2027 Summer Youth Program lottery registration runs Feb 1-15, 2027; it is a lottery, not first-come-first-served.
- Level
- competitive
- Time commitment
- Seven weeks, June 23 - August 14 (one week pre-season training plus six weeks on the job)
Upcoming sessions
- Jun 28, 2027 – Aug 20, 2027 · Mon, Tue, Wed, Thu, Fri · 8:30 AM – 4:00 PM · Charlestown, Pier 4
These are the dates the provider published. Confirm the current schedule and availability with them before you plan around it. Dates checked Nov 5, 2026.
Where it meets
Pier 4, Charlestown Navy Yard, Boston, MA
Parent reviews
One honest paragraph from a family who has been is worth more than any description. It takes about a minute.
Something wrong or out of date?
Tell us what should change. Accepted corrections earn points in your account.