The Eastport Yacht Club in Annapolis, Maryland, is currently recruiting for its 2026 summer instructional team, looking to fill both Lead and Assistant Instructor roles for its upcoming nine-week program.
The full summer program is slated to run from June 14 through August 13, with daily sessions held Monday through Friday from 9:00 am to 4:00 pm. For local residents, the club is also offering additional coaching opportunities during the spring and fall seasons.
Lead and Assistant Instructors Manage Summer Sailing Programs
The club’s hierarchy for the summer season divides responsibilities between two primary tiers of instruction. Lead Instructors are tasked with overseeing specific boat classes, managing curriculum, and supervising junior staff under the guidance of the Head Instructor and Program Director. To qualify for these positions, candidates must demonstrate several years of experience instructing summer sailing and show the ability to work productively without direct supervision.
Assistant Instructors serve a supporting role, assisting Lead Instructors and helping manage Instructors in Training. The responsibilities for this tier are more hands-on regarding maritime operations, as they are often required to drive a powerboat alone, deliver “chalk talks,” or supervise activities when a Lead Instructor is occupied. The compensation structure for the 2026 season is as follows:
| Position | Hourly Wage Range |
|---|---|
| Lead Instructor | $18 – $23/hr. |
| Assistant Instructor | $13.5 – $17/hr. |
Vessels Used in the Nine-Week Instructional Program
The Eastport Yacht Club’s instructional breadth covers a range of vessels suited for different skill levels, from beginners to advanced sailors. The fleet utilized during the nine-week program includes Optis, RS Zests, Melges 15s, and J22 keelboats.
Interested applicants are directed to submit a cover letter and resume to Preston Senior, the Waterfront Manager, via email at waterfront@eastportyc.org.
