We're Hiring

Tall Ship Windy is actively seeking individuals with 100-ton or above U.S. Coast Guard Merchant Mariner Master credentials. We are actively seeking a full-time Captain for April through September for Tall Ship Windy in Chicago. This individual will also have the opportunity to work October through March as a Captain in the U.S. Virgin Islands for Seas the Day Charters USVI. The qualified individual will have significant experience at the helm on vessels between 50 and 100 tons and must also possess a sailing endorsement on their credential. Tall Ship Windy and Seas the Day Charters offers excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator. 

HIRING FULL AND PART-TIME SENIOR DECKHANDS. The Senior Deckhand is responsible in ensuring that all crew are informed of the ship’s policies, the purpose of those policies and the critical nature of each crew persons supporting of those policies. The Senior Deckhand is the second in command and will act with integrity as a supporting conduit between the Captain and the crew. The Senior Deckhand will fulfill all duties and tasks delegated to them by the Captain. These duties and tasks will include bridge watches, harbor watches, anchor watches, administrative work, safety management, physical labor in cleaning, prepping, painting, repairing and maintaining of all surfaces and equipment. The duties and responsibilities also include but are not limited to operating the sails and rigging of Windy underway, maintaining Windy in good working order, ensuring safety of guests and fellow crew while sailing, performing storytelling and other artistic events and providing unique sailing experiences for guests. The Senior Deckhand oversees the preparation of the vessel for sea and berthing and briefs crew members on their deck duties at these times. When guests are on board they oversee and participates in deck operations in respect to guest activities. The Senior Deckhand must be familiar with all aspects of the vessel and be able to assume command if the Captain is absent or incapacitated. Tall Ship Windy offers crew quarters during season in Chicago which runs from mid-April through September. Additionally, qualified individuals are given the opportunity to work at our sister company, Seas the Day Charters in the U.S. Virgin Islands from October through March. Tall Ship Windy and Seas the Day Charters offer excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator. 

NOW HIRING BOTH EXPERIENCED AND THOSE WILLING TO LEARN. Outstanding deckhands provide the foundation of any well-run ship. They are integral to the success of any maritime charter. Tall Ship Windy is seeking both qualified deckhands with previous experience. For the right individual, Tall Ship Windy is also willing to hire deckhands in training. The deckhand will fulfill all duties and tasks delegated to them by the Captain and Senior Deckhand. Duties of deckhands generally include: 1) Perform sailing operations of the vessel under the supervision of senior crew and Captain of the ship. 2) Assist with dockside guest services and promotion of the ship’s excursions. 3) Other duties may include performing educational demonstrations, storytelling and attending and participating in promotional activities arranged by or on behalf of the Company. 4) Reasonable duties also may include assisting the Company in flexible job roles from time-to-time, including office work, maintenance projects, bartending and box office staffing. The Deckhand is responsible for cleaning and maintaining the exterior and technical spaces of the vessel to standards and procedures set down by the Captain and Senior Deckhand. The deckhand is to always be neat and in the correct uniform – worn correctly – and that proper routines and disciplines as described within the ship’s policies and standing orders are followed. The deckhand must have a full working understanding of all safety procedures and equipment. Tall Ship Windy offers crew quarters during season in Chicago which runs from mid-April through September. Additionally, qualified individuals are given the opportunity to work at our sister company, Seas the Day Charters in the U.S. Virgin Islands from October through March.

Seas the Day Charters USVI is actively seeking individuals with 100-ton or above U.S. Coast Guard Merchant Mariner Master credentials. We are actively seeking full-time captains year round in St. Thomas, USVI. The qualified individual will have significant experience at the helm on vessels between 50 and 100 tons and must also possess a sailing endorsement on their credential. Seas the Day Charters USVI offers excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator. 

For those that want a fun atmosphere while enjoying the crystal blue waters of the Caribbean, a charter crew position with Seas the Day Charters USVI is for you. We are seeking experienced crew who desire full-time positions in the U.S. Virgin Islands.