And we’re sailing! Our season started in April.

Full-Time Year-Round Captain

  • Full Time
  • Annapolis, MD
  • $47,500 Salary + $15,000 avg in Gratuities USD / Hour

Website Running Free Inc./Schooner Woodwind

Annapolis Sailing Cruises


  • 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


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


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


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.


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.

Schooner Woodwind & Woodwind II are identical 74-foot sailing yachts available for public sailing and private charter departing from the Annapolis Waterfront Hotel.

Schooner Woodwind also manages and maintains the 360 feet of wharf side dock space (available for transient dockage) on behalf of the Annapolis Waterfront Hotel.

Since 1993 the Woodwinds have been a family-owned and operated company.

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)
(410) 263-1981
(410) 280-6952
Schooner Woodwind