2024 Sailing Season is coming! See you April 13, 2024!

Dock Staff

  • Seasonal
  • Annapolis, MD
  • $15.00 plus tips USD / Hour

Website Running Free Inc./Schooner Woodwind

Annapolis Sailing Cruises


  • Handle dock lines for Woodwind and Woodwind II
  • Assist in docking visiting boats
  • Coordinate wharf side space to facilitate commercial, transient, and overnight dockage
  • Collect payment for transient dockage
  • Assist Customer Service Staff
  • Assist Woodwind Crew & Maintenance staff
  • Assist hotel & restaurant guests regarding:
    • Woodwind
    • Hail Water Taxis
    • Local knowledge
    • Dock space availability
  • 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 have boating, hospitality and customer service experience and be a friendly, organized and safety-minded individual.


The successful candidate should have the following qualifications:

  • Excellent oral communication skills
  • Knowledge of boats and boat docking practices
  • Able work outside for 10-12 hour shifts
  • Adept at knot tying
  • Alert, Reliable and Consistent
  • Able to complete daily check lists
  • Able to complete bi weekly inventory checks
  • Open to new ideas, and a “team-player”
  • Must have or get Maryland Boater Safety Certification prior to employment start date
  • Knowledgeable about the area
    • Annapolis
    • Chesapeake Bay
  • Count cash tips and report during clock out.
  • Must be able to lift/carry up to 50 lbs repeatedly
  • Must be able to use a hand-truck
  • Must be able to catch and throw dock lines
  • Must be able to load and unload pickup truck
  • Be able to prioritize work flow
  • Must be physically agile and able to tie up boats to pilings and cleats on the dock
  • Comfortable working closely with other employees in tight quarters
  • Comfortable working around large groups customers, restaurant and bar patrons
  • Easy going demeanor to handle conflict resolution; ability to remain calm in high pressure situations
  • Time and space management skills


This hourly position pay rate is $15.00 an hour plus tips (average $18/hour including tips). There is a work commitment incentive for qualified employees.


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