FacilityCaribbean Sail Training Ltd.
LocationFalmouth, St Pauls
Available10/01/2026
ASA LevelsSkipper and Instructor
Contact NamePeter Anthony
Contact Emailpeter@sailtrainingcaribbean.com
Contact Phone(268) 720-5313
Websitewww.caribbean-sail.com
NotesWe are looking for a skipper for our Farr 65 sailing yacht. Built in 1999 she has circumnavigated plus sailed many transatlantics . She is now based in Antigua and operates in the Caribbean offering racing in all of the Caribbean regattas , adventure sailing to the islands less visited and developing a number of training and passage making trips Candidates must have a solid racing background ideally on larger yachts, be safety orientated, client focussed and ideally a training background. Our clients vary from enthusiastic novices to experienced sailors with or without a racing background. Could possibly suit a couple. We do have a quiter summer season but always plenty to do in CST and our sister company Ondeck. See https://photos.app.goo.gl/7NVb6etHGT3HuvCJA for some action pictures
Posted On07/07/2026
FacilitySail Monterey
LocationMonterey, CA
Available08/01/2026
ASA LevelsAny
Contact NamePaul Bowker
Contact Emailpaul@sailmonterey.com
Contact Phone(831) 372-7245
Website
NotesSail Monterey is hiring ASA instructors and charter captains! Please email or call Paul to apply. We have a fleet of 6 boats, a fun team, and a beautiful location. Thank you!
Posted On07/01/2026
FacilitySail Monterey
LocationMonterey, CA
Available09/01/2026
ASA LevelsAny
Contact NamePaul Bowker
Contact Emailbook@sailmonterey.com
Contact Phone(831) 372-7245
Website
NotesSail Monterey is hiring ASA instructors and Captains. Offering ASA 101, 102, 103, 104, 105, & 106 + fun sailing adventures to our club members. Join our fun team and vibrant community in Monterey. Contact Capt. Paul to apply 🙂
Posted On07/01/2026
FacilityBBYC Sailing School
LocationMattapoisett, MA
Available06/15/2026
ASA Levels101, 103 and/or 104
Contact NameSteve Robinson
Contact Emailbuzzardsbayyachtcharters@gmail.com
Contact Phone(401) 575-3299
Websitewww.buzzardsbayyachtcharters.com
NotesSeasonal instructor needed. Our fleet includes an Ensign 22 for 101 and a Pearson 35 for Coastal Cruising and Intro to Bareboat Charters. Charter captain opportunities are also available for candidates with at least an OUPV six pack license. Visit our website at www.buzzardsbayyachtcharters.com to learn more about our program.
Posted On06/15/2026
FacilitySeattle Sailing Club
LocationSeattle, WA
Available06/11/2026
ASA Levels201 and up
Contact NameAllison Huyck
Contact Emailallison@seattlesailing.com
Contact Phone(206) 782-5100
Websitewww.seattlesailing.com
NotesSeattle Sailing Club is hiring friendly and professional sailing instructors for flexible, part-time, year-round opportunities in Seattle. Instructors teach ASA certification courses, private lessons, clinics, corporate team-building events, and member programs while creating a safe, engaging learning environment on the water. Competitive pay includes tips, a matching 401(k), and perks like free sailing lessons, discounted family lessons, pro shop discounts, and boat use privileges. Since 1968, Seattle Sailing Club has been one of the West Coast’s largest ASA schools, known as a fun and welcoming place to learn and sail. Qualified candidates must hold a U.S. Coast Guard Captain’s License, ASA Instructor certification (ASA 201 or higher), current First Aid/CPR certification, and the ability to be enrollment in a maritime drug testing program. Strong keelboat sailing skills, a positive attitude and a passion for teaching are essential.
Posted On06/11/2026
FacilityGo Sail Flathead Lake
LocationBig Arm, MT
Available06/10/2026
ASA Levels201
Contact NameGenevieve Evans
Contact Emailinfo@gosailmontana.com
Contact Phone(406) 201-9750
Websitegosailmontana.com
NotesThe Opportunity: Your Montana "Workcation" Spend your summer in the heart of Big Sky Country! This isn't just a job; it’s an opportunity to live and work in one of the most beautiful recreation areas in the US. With a 4-day work week, you’ll have ample time to explore, hike, camp, and enjoy the mountain air. Job Title: Sailing Instructor & Charter Captain Location: Big Arm, MT and/or Dayton, MT (Flathead Lake) Term: Seasonal (May – September) Schedule: 4-6-Day Work Week (Flexible 4 day min) Go Sail Flathead Lake is the premier ASA Sailing School in the Inland Northwest. Located on the stunning Flathead Lake—the largest natural freshwater lake west of the Mississippi—we operate on a Glacier National Park-fed mountain lake known for its consistent 10-20 knot winds and breathtaking scenery. We pride ourselves on delivering high-quality sailing education and unforgettable charter experiences. Perk: Employees enjoy free use of our sailing equipment for personal recreation when not in use. Competitive pay $250-350 per day BOE; Independent Contractor (1099) status. If you are a professional sailor looking for a rewarding summer on the water, we want to hear from you. Review our offerings at https://www.gosailmontana.com/. Send your resume and a brief introduction to us.
Posted On06/02/2026
FacilityPacific Sail
LocationSanta Cruz, CA
Available06/07/2026
ASA Levels101,102,103,104
Contact NameCharlie Wilcox
Contact Emailcharlie@pacificsail.com
Contact Phone(831) 854-7482
Websitewww.pacificsail.com
NotesUnder new ownership! We are seeking USCG skippers 6-pak or better and contract instructors for 101-104 in Santa Cruz, CA. These classes, Skippered charters and our own skills and race clinics, please send your inquiries and availability to charlie@pacificsail.com. Talk soon! -Charlie
Posted On06/02/2026
FacilityLearn to Sail San Diego
LocationSan Diego, CA
Available06/01/2026
ASA Levels201, 203 and 204 preferred
Contact NameMelinda Rose
Contact Emailmelinda@learntosailsandiego.com
Contact Phone(619) 316-6430
Website
NotesLooking for a qualified instructor to teach weekend 101s and potentially longer 4-6-day 101/103/104 courses. Must have a USCG license and be CPR certified. Reach out for more details!
Posted On05/28/2026
FacilityLake St. Clair Sailing School
LocationHarrison Twp, MI
Available06/01/2026
ASA Levels201. 203, 204
Contact NameRanam Kazziha
Contact Emaillscsailingschool@gmail.com
Contact Phone(248) 909-9428
Website
NotesWe are looking for Captains and ASA instructors to teach ASA 101, ASA 103 and ASA 104 in Harrison Township Michigan
Posted On05/27/2026