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
  • Crew Members aboard the Schooners
  • Dock Staff at the Annapolis Waterfront Hotel
  • Customer Service for Ticket Sales and Dock Space

Schooner Woodwind Waterfront Facility Manager Description

This is a full time, year round salaried position with health benefits. The Waterfront Facilities Manager manages the Schooner Woodwind’s dockside office and staff, including customer service representatives and dock staff for very small wharf-side marina. Other duties include managing inventory, placing orders with vendors and picking up supplies on a weekly basis for boat and dock use.  This person will act as a front-line person for our customers and concierge for visitors by answering questions and providing directions and manage their staff to do the same, which include selling tickets by phone and in-person for Schooner Woodwind.

Schooner Woodwind Event Sales Description

This is a full time position with the company as a Event Sales Person. This is a salaried position with health benefits. Fun place to work in a small office. Come be part of the Woodwind family. Please click above link for job description.

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. Only a few of these may be “summer jobs” for college students. 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.

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.

Work on the Schooner Woodwind on the Chesapeake Bay

Work on the Schooner Woodwind on the Chesapeake Bay

Schooner Woodwind Employment Application in Acrobat .pdf format (handwritten fill in)

Schooner Woodwind Employment Application – Word Format (handwritten fill in)

Fax: 410-280-6952
Mail: 1930-A Lincoln Dr., Annapolis, MD 21401
Email: info@schoonerwoodwind.com

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