Captains & First Mates

We are in need of 6 Pack or Master Captains and crew members with sailing experience on the Chesapeake Bay. Please send your resume to info@chesapeakewindsailcruises.com or by completing the form below


We are seeking a full charge part-time bookkeeper who has over 5 years of experience in QuickBooks Pro and has experience in the charter, tour, sightseeing or amusement business. Please send your resume to info@chesapeakewindsailcruises.com or use the below form


Responsible for the check in and cashier duties with the passenger, assisting the first mate with stocking and restocking of the vessel before the cruise and when the cruise returns to the dock. Setting up the check-in table, banners and all materials necessary to start the day in order to receive passengers and at the end of the day store materials on the boat.

Standard Specifications:

Requirements are representative of minimum levels of knowledge, skills and/or abilities. To perform this job successfully, the incumbent will possess the abilities or aptitudes to perform each duty proficiently



  • Bright, High-Energy, Go-Getter with excellent presentation of self.
  • Ability to provide a high level of service and a memorable experience for our passengers
  • Must be able to work flexible hours including evenings, weekends and holidays.
  • Capable of multi-tasking.
  • Professional work ethic, enthusiastic and good humored.
  • Able to perform necessary cleaning tasks to keep the boat safe, clean and operable.
  • Able to work alone and as part of a team
  • Appreciates and respects nature and our local waterways.
  • Good organizational skills
  • Ability to communicate well with passengers and co-workers


  • High school graduate
  • Hospitality and or Boating experience.
  • CPR, First Aid, AED certified
  • Knowledge about local waterways
  • Knowledge of surrounding environment including the bay and its history.


  1. Ability to communicate effectively in English with members/guests/employees to their understanding
  2. Ability to write legible communication and directions
  3. Ability to safely operate around the boat
  4. Ability to focus on passenger needs
  5. Ability to prioritize, organize and make good judgments
  6. Ability to maintain confidentiality of passengers’ information and company data
  7. Ability to perform assignments with minimal supervision.

    1. Working Conditions:

      Most tasks are performed outdoors in variable weather conditions, including hot, windy and wet weather. Temperature can be extreme but are usually moderate. Frequently works near moving/mechanical parts and on local waterways.

      Physical Demands:

      While performing the duties of the job, the employee is required to reach with arms and hands; bend and stoop; remain at post standing and sitting for extended periods of time.
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