
Website Running Free Inc./Schooner Woodwind
Annapolis Sailing Cruises
CAPTAIN RESPONSIBILITIES
- Excellent skills in boat handling
- Share the adventure of sailing with our guests from a historic, environmental and geographic point of view with a sense of humor
- Ability to set the proper atmosphere for the safety of the passengers and crew
- Maintenance of our vessels
- Regular engine maintenance
- Upkeep of brightwork, rigging, plumbing
- Other system maintenance.
- During the off season (November through March), share the responsibility to ready the boat for the following season
- More complex maintenance skills in woodworking, painting, varnishing, etc.
- Help with preparation for USCG inspections
- In emergency situations, employees may need to change their normal operations and help secure business property, assets and/or vessel safety
BACKGROUND
The successful candidate will be a friendly and safe professional captain who will have several years of experience:
- Working as a captain, aboard a sailing vessel doing similar activities as outlined above
- Managing a crew and maintenance workers to get work done timely and on task
- Will have the maintenance skills to carry out the tasks described above
QUALIFICATIONS
The successful candidate will have a valid USCG License as a Master of Auxiliary Sail Vessels with a minimum of an Inland rating and 50 Gross Tons, a Marine Radio Operators Permit, a clean USCG record, and have no objections about being enrolled in a random drug-testing program. The person must also have the following qualifications:
- Excellent oral communication skills
- Expertise in Maintenance organization and implementation
- Be a skillful leader and trainer for crew
- Open to new ideas, and a “team-player”
- Must look at the responsibility of these boats as if they were their own
COMPENSATION
The full time position would be salaried with a starting salary around $47,500 depending on experience. Gratuities also add up to additional compensation and averages around $15,000. If the captain performed as expected and was able to take on more responsibility reasonable increases could be expected. Weekly workload ranges from 40-50 hours, and there is a generous PTO policy during the winter months. We also offer health benefits and retirement plan options.
OTHER COMPENSATION
Our standard employee perks include the ability to bring friends & family aboard the Woodwinds when seats are available and employee discounts at Pusser’s Caribbean Grille Restaurant and Store.
To apply online, click on the "Apply for Job" button below. If you prefer to download an application and mail or fax to us, you may download a PDF application.


- Offsite Office
- 1930-A Lincoln Drive, Annapolis, MD 21401
(Monday-Friday, 9-5) - Onsite Office & Boats
- 80 Compromise Street, Annapolis, MD 21401
(Everyday, April 15-October 31) - Phone
- (410) 263-1981
- Fax
- (410) 280-6952
- info@schoonerwoodwind.com
- Web
- www.schoonerwoodwind.com