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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. You can help!

1Captains - Full & Part Time
We are seeking to hire Full & Part-time USCG licensed captains 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. You will ensure that all procedures as outlined in the company's 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. Your work schedule will rotate with other captains. 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 preferable to include three (3) years as a USCG licensed captain with an outstanding record on tour or sightseeing boats. Department of Transportation worker's references, as well as other work related references, will be requested and checked. You will be subjected to drug testing and background check.
2First Mates
We are seeking first mates for our sailing season which is May 1st 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 sailing 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.
3Bookkeeper/Office Manager - Part-time
We are seeking a full charge part-time bookkeeper/office manager to work Monday through Friday, 15 to 30 hours per week and up to 30 hours per week during our peak season (April to October). The ideal candidate will have an AA, BA or better in accounting with 10 years or more of experience in accounting using QuickBooks Pro. Strong background in AP, AR, credit card processing, general ledger, etc. Must also possess good office management skills including, but not limited to, working well with others, time management, crew scheduling, good customer service skills, excellent knowledge of Excel, Word and Outlook. You will interact with staff and crew members and work closely with the US Coast Guard regulations and requirements. Experience in the boat charter, tour, sightseeing or amusement business is a plus. Please only if your background meets all of the above listed requirements.
4Dock 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.
5Walking Tour Guide

You will lead Walking Tours in North Beach and Chesapeake Beach, Maryland. These walking tours will consist of a 60 to 90 minute history and scenic tour to points of interest in North Beach and in Chesapeake Beach respectively. Training will be provided.

The ideal candidate will have 5 years or more of docent or guide experience, knowledge of the Twin Beaches area and the love of sharing information with strangers. You must possess good communication skills, able to walk one mile or more, able to move people along in a timely manner, and know first aid and CPR.

The season will start mid-April and conclude at the end of October. Compensation is based on your experience.


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    Chesapeake Windsail Cruises