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. Open positions are in red. as of 5/13/21, we do not have any open positions, check back in July. Employment opportunities may include:
Crew on the Woodwind, if you have sailing experience.
- Event Sales Associates
- Administrative Assistant
- Event Sales Manager
- Waterfront Facility Manager
- Office Manager
- USCG Licensed Captains
- Crew Members/Deckhands
- Dock Staff at the Annapolis Waterfront Hotel
- Customer Service for Ticket Sales and Dock Space
Event Sales Associate Job Description
We are looking for a full time, year round Event Sales Associate to work in our business office. This is a salaried position with benefits. Please include your resume with your application.
Administrative Assistant Job Description
We are looking for an Administrative Assistant to work in our business office assisting the Sales Department. This is a seasonal hourly position.
USCG Licensed Captain Job Description
We are looking for a full time, year round captain that has some experience on a passenger sailing vessel. Salary position, plus gratuities and other benefits.
Crew/ Deckhand 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. Taking applications now for the 2021 season.
Waterfront Facility Manager Job Description
We are looking for a full time, year round Waterfront Facility Manager to oversee the Waterfront Dock staff and Woodwind Customer Service Representatives. Salary position, plus gratuities and other benefits.
Customer Service Ticket Sales Office
Customer Service/Ticket Sales 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. Taking applications now for the 2021 season.
Dock Staff at Annapolis Waterfront Hotel
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. Taking applications now for the 2021 season.
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
Fax: 410-280-6952
Mail: 1930-A Lincoln Dr., Annapolis, MD 21401
Email: info@schoonerwoodwind.com
