Running Free Inc. has multiple facets to the business of running the Schooner Woodwind and Woodwind II  and the docks at the Annapolis Waterfront Hotel. Employment opportunities may include:

Crew on the Schooner Woodwind in Annapolis

Crew on the Woodwind, if you have sailing experience.

  • Event Sales Associates
  • Event Sales Manager
  • Waterfront Facility Manager
  • Office Manager
  • USCG Licensed Captains
  • Crew Members aboard the Schooners (taking applications now)
  • Dock Staff at the Annapolis Waterfront Hotel (taking applications now)
  • Customer Service for Ticket Sales and Dock Space (taking applications now)

Schooner Woodwind USCG Licensed Captain Job Description

We are looking for a full time, year round captain that has some experience on a passenger sailing vessel. This position is open now. Salary position, plus gratuities and other benefits.

Schooner Woodwind Crew Job Description

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 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.

Customer Service Ticket Sales Office for Schooner Woodwind

Customer Service Ticket Sales Office

Schooner Woodwind Customer Service Job Description

In addition to the crew positions, we hire two customer service representatives. One is full time, and one is part time, both positions run from early April through the end of October. All successful candidates must have good computer skills for our POS system, good phone skills, and be able to communicate well in person.


Dock Staff at Annapolis Waterfront Hotel

Dock Staff at Annapolis Waterfront Hotel

Schooner Woodwind Dock Staff Job Description

We typically need two dock staff members beginning in mid-April. One is a full-time job, the other a part-time job. The successful candidate must have knowledge of docking procedures and be able to handle ropes (lines). A safe boater’s license is required. Hourly wages plus tips. The dock job is located at the Annapolis Waterfront Hotel.

 All interested applicants should fill out our application and forward a completed copy to us either by fax, snail mail or email.

Application (PDF) Application (Word)
Work on the Schooner Woodwind on the Chesapeake Bay

Work on the Schooner Woodwind on the Chesapeake Bay


Fax: 410-280-6952
Mail: 1930-A Lincoln Dr., Annapolis, MD 21401

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