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

Full-Time Hourly Captain

  • Seasonal
  • Annapolis, MD
  • Starting wage $22/hour + Gratuities: See Details 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.
  • Assist in maintenance of vessels as needed.
  • 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.


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
  • 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.


This position requires at least three or four days a week, up to 12 hours per day. The season is from Early April through the end of October.


The full-time position would be seasonal and paid on an hourly basis. There is a strong possibility that a winter maintenance job would be offered as well for the right candidate. We will offer a starting hourly rate of $22 per hour for excursion (public sail) work, plus cash tips. The hourly rate will increase to an additional $20 per hour while the boat is contractually under charter and $10 when there is a contracted group sail. This does not include time getting the boat ready or closing her down. The average hourly wage of tips averages out to an additional $14 an hour.


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