You are only a few steps away from a wonderful day on the beautiful Chesapeake Bay.

Select your Cruise!

Chesapeake Windsail Cruises is devoted to delivering a higher passenger sailing experience, a key part of our commitment to refined cruising. Passengers can expect great hospitality, exceptional seamanship, world class yachts and an elegant and welcoming ambiance with the goal of creating lasting and cherished memories.


Chesapeake Windsail Cruises is seeking a USCG licensed captain with a sailing endorsement and experience on the Chesapeake Bay. The ideal candidate must have mechanical & maintenance experience, good communication skills, knowledge of the Chesapeake Bay and an understanding of the Chesapeake Bay’s history. You will rotate as cruise captain and ensure that all procedures as outlined in the Operation-Boat Manuals are carried out. This includes, but is not limited to, maintenance and repairs on the vessel. Maintenance on the vessel includes maintaining the appearance of the vessel and regularly scheduled engine maintenance and repairs such as oil changes, filter changes, impeller changes, and belt changes. Other responsibilities include preparing the vessel for the annual Coast Guard inspection, pre-cruise preparation, adherence to cruise scripts, supervision of crew, proper piloting of vessel, and adherence to all Coast Guard rules and regulations. High school diploma or equivalent required is a minimum. Must currently possess a six Pack or Master Captains license with a sailing endorsement and a satisfactory record. Minimum of five (5) years of marine experience' preferably to include two (2) years as a captain with an outstanding record on tour or sightseeing boats.

First Mates

We are seeking five first mates for our sailing season which is May 1 through October 12th. You must love sailing, the bay, people and have a great personality. As first mates, you will assist the captain and the passengers while on the bay and at the dock. Sailing experience as a first mate or a skipper is a must. Great opportunity to meet nice people from around the world, earn money for something that you love, and sail on the Chesapeake Bay! Experience in the tour and activity industry is a plus.


We are seeking a full charge part-time bookkeeper. The ideal candidate will have a AA, BA or better in accounting with 10 years or more of experience in accounting using QuickBooks Pro. Experience in the boat charter, tour, sightseeing or amusement business is a plus. Pay is commensurate with your experience.

Dock Agent

Responsible for ticket sales, check in and cashier duties with the passengers, assisting the first mate with stocking and restocking of the vessel before the cruises and when the cruises 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 away.



  • 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 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


  • 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 passengers/guests/employees to their understanding
  2. Ability to safely operate around the boat
  3. Ability to focus on passenger needs
  4. Ability to prioritize, organize and make good judgments
  5. Ability to maintain confidentiality of passengers’ information and company data
  6. Ability to perform assignments with minimal supervision.

Working Conditions:

Most tasks are performed outdoors in variable weather conditions, including hot and windy 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; may be required to lift and/or move up to 50 pounds.
This form is for employment use ONLY! If you use this form for any purpose other than employment, your e-mail address will be BLOCKED!

Input this code: captcha