Deckhand & Guest Services – 49-Passenger Sailing Catamaran

The Role

Join the crew of a premier 48-foot sailing catamaran for the 2026 charter season. We are looking for high-energy, safety-conscious individuals who can balance the technical demands of a large sailing vessel with top-tier hospitality. You aren't just a deckhand; you are the face of the guest experience on the water.

Key Responsibilities

• Vessel Operations: Assist with line handling, docking maneuvers, raising/trimming sails, and occasional helming under Captain’s supervision.
• Safety & Compliance: Maintain a "head on a swivel" approach to passenger safety and strictly follow USCG-regulated safety protocols.
• Hospitality & Service: Prepare and serve beverages, engage with guests, and provide information about the vessel and the Chicago skyline.
• Vessel Care: Participate in daily "yacht-standard" cleaning, detailing, and basic maintenance to keep the catamaran in pristine condition.

Requirements & Qualifications

• Age: Must be 21+ years old (due to alcohol service requirements).
• Certifications: Must have a current BASSET certification or be willing to complete training prior to the first charter.
• Drug Testing: Must be enrolled in (or willing to enroll in) a USCG-approved random drug testing program. This is a safety-sensitive position with zero tolerance.
• Physical Ability: Must be able to lift and carry 50 lbs and remain standing/active for 8–10 hour shifts in various weather conditions.
• Experience: Comfortable on the water with a basic understanding of sailing/boating. Professional maritime experience is a plus, but we will train the right personality.

Ideal Candidate Profile

We are looking for someone who is as comfortable hauling a line as they are hand-delivering a drink to a guest. You should be proactive, punctual, and thrive in a fast-paced, outdoor environment.

Professional Growth: This position is ideally suited for maritime professionals or students looking to build a career on the water. We provide documented sea service letters, making this an ideal role for candidates seeking to qualify for their USCG Sail Auxiliary Endorsement or accumulate hours toward a Master’s License.

Availability

As a premier weekend destination on Lake Michigan, our peak hours occur on Saturdays and Sundays. Candidates must be available to work at least one full weekend day (Saturday or Sunday) throughout the season.

Pay: From $22.00 per hour

Expected hours: 12.0 – 40.0 per week

Work Location: In person