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

Crew/ Deckhand

  • Seasonal
  • Annapolis, MD
  • $27/avg including tips USD / Hour

Website Running Free Inc./Schooner Woodwind

Annapolis Sailing Cruises

Every year, we will need to fill several full-time and part-time crew member positions aboard our twin schooners, Woodwind and Woodwind II. Job Openings will begin in early March and be staggered through mid-May.  Ideally, those applicants that can begin work in early April and work through October are preferred. We require some sailing experience and previous jobs working with the public. We offer good wages plus tips, a fun environment, a team approach, and supportive management.  Only people 18 or older should apply due to the requirement of serving alcohol on our cruises.  We are taking applications now for the 2023 season (start in March – May through the end of October)


  • Prepare the vessel for passengers, which includes cleaning topside and below; stowing supplies; obtaining ice; preparing sailing gear and sails, etc.
  • Assist in docking, passenger embarkation and disembarkation.
  • Sail handling and safety according to captain’s orders
  • Welcome passengers and casual conversation.
  • Serve food and drinks (including alcoholic beverages)
  • Be responsible in the handling of credit cards and recording beverage inventory information.
  • Stow gear and clean at end of last shift
  • Assist in routine maintenance such as varnishing, painting, cleaning.
  • Demonstrate life jacket use.
  • Understand concepts of basic sailing
  • Promote Woodwind & Waterfront services and merchandise.
  • Pool all tips equally
  • Crew must learn how to handle intoxicated guests and how to prevent guests from becoming intoxicated
  • 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 safety-minded crew member who will have some experience crewing aboard a sailing vessel whether recreational or commercial.


The successful candidate should have the following qualifications:

  • Excellent oral communication skills
  • Open to new ideas, and a “team player”
  • Must be enthusiastic to learn and to share with customers their love for sailing


  • Shifts can be 12 hours long for full time work, and the boat can go out up to four times daily.
  • Candidates should be able to carry a case of water on and off the boat. (30 lbs)
  • The companionway ladder will need to be utilized over 40 times a day during a 12-hour shift
  • The candidate will need to be able to work in tight spaces and perform engine and bilge checks almost daily.
  • Temperatures in the summer can reach over 100 degrees, and this is outside work. Some shade is available by the sails, but not all the time.


  • All crew members start at $13.25/hr, plus cash tips. After crew training is completed, crew members will earn additional wages for Private Charters & Group Sales. When all gratuities and additional wages are added in, the average hourly wage is approximately $27.00. There is a work commitment incentive for qualified employees.


  • Our standard employee perks include the ability to bring friends & family

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