We're Hiring!

Tall Ship Windy is now hiring for the 2024 season starting in April

We are actively seeking U.S. Coast Guard licensed Captains, Senior Deckhands, Deckhands, Guest Services and Bartenders. At Tall Ship Windy, you will enjoy excellent pay, an exciting and fun atmosphere and the opportunity to learn mariner skills. In addition, members of the Tall Ship Windy team have the opportunity to work year-round by working in the Winter months at our sister company, Seas the Day Charters in the U.S. Virgin Islands (www.seasthedayusvi.com).

Select, qualified candidates are offered crew quarters aboard Tall Ship Windy berthed at Navy Pier during the season.

For consideration for any of these positions, please email your resume to [email protected].

U.S. Coast Guard Licensed Master (Captain)

Hiring Full-Time, Year Round Captains for Chicago and U.S Virgin Islands

Tall Ship Windy and Seas the Day Charters USVI are 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 USVI 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. For consideration, please email your resume to [email protected].

Hiring - Senior Deckhands

Hiring Full and Part-Time Senior Deckhands

The Senior Deckhand is responsible for 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 and physical labor in cleaning, prepping, painting, repairing and maintaining 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 crewmembers on their deck duties at these times. When guests are on board they oversee and participates in deck operations with 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 the 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.

Full and Part Time Deckhands

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 and 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 relations 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 may also 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 stated 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.

Bartenders and Servers

Hiring Full and Part Time on Navy Pier in Chicago

We are looking for enthusiastic Bartenders and Servers to provide an excellent guest experience. Good Bartenders will be able to create classic and innovative drinks that exceed guests’ needs and expectations. Our bartenders and servers have outstanding compensation which includes salary and tips.

Responsibilities include: Preparing alcoholic or non-alcoholic beverages for Tall Ship Windy guests, interacting with guests, taking guests’ orders and serving snacks and drinks, assessing guests’ needs and preferences and making recommendations, mixing ingredients to prepare cocktails, assisting with planning the bar menu, check guests’ identification and confirm it meets legal drinking age requirements, restocking and replenishing bar inventory and supplies, staying guest focused and nurturing an excellent guest experience and complying with all food and beverage regulations.

Requirements for this position include: resume and proven working experience as a Bartender or Server, excellent knowledge of mixing, garnishing and serving drinks, computer literacy, a positive attitude and excellent communication skills, ability to keep the bar organized, stocked and clean, relevant training and license.

Tall Ship Windy offers select employees crew quarters aboard Tall Ship Windy during the 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.