Private Executive Boat Captain

Looking for a responsible, experienced, and engaging Boat Captain for a 46' Sea Ray Sundancer based in Chicago.

The position will primarily involve operating and maintaining the vessel on Lake Michigan and throughout the Chicago area. Ideally, we are looking for someone who can start by late September or early October 2026 to assist with preparing the boat for winter storage and become familiar with the vessel. The position would then transition into a full-time Captain role for the 2027 boating season.

This is a seasonal position focused on the boating season, with some additional responsibilities in the fall to help prepare the vessel for winter storage and in the spring to get the boat ready for launch. We are looking for someone who takes pride in the vessel, is comfortable handling maintenance and operational needs, and can provide a safe and enjoyable experience for everyone onboard.

Pay Range: Starting at $8,000 per month, depending on experience

Responsibilities

• Safely operate and navigate the vessel on Lake Michigan and throughout the Chicago area
• Maintain the appearance and operation of the vessel before, during, and after use, including completing pre- and post-trip inspections
• Provide exceptional customer service with an emphasis on safety and creating an enjoyable experience for guests
• Ensure the vessel is clean, organized, and properly stocked with necessary supplies
• Assist with routine maintenance, troubleshooting, and coordinating with marine service providers when needed
• Assist with launching, docking, fueling, winterization, and removing the boat from the water
• Assist with preparing the vessel for winter storage in the fall and preparing it for the upcoming boating season in the spring
• Monitor weather and lake conditions and make sound decisions regarding safe operation
• Ensure all required safety equipment and onboard systems are in good working order
• Handle projects related to the boat, its maintenance, and overall operation
• Maintain records and communicate any maintenance, safety, or operational issues as needed

Qualifications

• Experienced and properly licensed/certified to operate a vessel of this size
• Significant experience operating boats on Lake Michigan strongly preferred
• Comfortable navigating Chicago's harbors, marinas, and waterways
• Strong knowledge of boating safety, navigation, and weather conditions
• Basic mechanical and boat maintenance knowledge
• Comfortable docking and maneuvering a 46' vessel in tight spaces and busy marinas
• Professional, responsible, personable, and engaging
• Strong customer-service skills and a focus on safety
• Flexible schedule, including weekends and holidays during the boating season
• Located in the Chicago area or willing to travel to the Chicago harbor/marina
• Clean boating and safety record preferred
• Experience with Sea Ray or similar-sized vessels is a plus