Private Executive Boat Captain

Looking for a responsible, experienced, and engaging full-time 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 year-round position, with responsibilities extending beyond simply operating the boat during the boating season. 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: 6-8k a month - depending on experienceResponsibilities:Safely operate and navigate the vessel on Lake Michigan and throughout the Chicago areaMaintain the appearance and operation of the vessel before, during, and after use, including completing pre- and post-trip inspectionsProvide exceptional customer service with an emphasis on safety and creating an enjoyable experience for guestsEnsure the vessel is clean, organized, and properly stocked with necessary suppliesAssist with routine maintenance, troubleshooting, and coordinating with marine service providers when neededAssist with launching, docking, fueling, winterization, and removing the boat from the waterHelp prepare the vessel for winter storage in the fall and prepare it for the upcoming boating season in the springMonitor weather and lake conditions and make sound decisions regarding safe operationEnsure all required safety equipment and onboard systems are in good working orderHandle projects related to the boat, its maintenance, and overall operationMaintain records and communicate any maintenance, safety, or operational issues as neededQualifications:Experienced and properly licensed/certified to operate a vessel of this sizeSignificant experience operating boats on Lake Michigan strongly preferredComfortable navigating Chicago’s harbors, marinas, and waterwaysStrong knowledge of boating safety, navigation, and weather conditionsBasic mechanical and boat maintenance knowledgeComfortable docking and maneuvering a 46' vessel in tight spaces and busy marinasProfessional, responsible, personable, and engagingStrong customer-service skills and a focus on safetyFlexible schedule, including weekends and holidays during the boating seasonLocated in the Chicago area or willing to travel to the Chicago harbor/marinaClean boating and safety record preferredExperience with Sea Ray or similar-sized vessels is a plus