Seasonal | Spring–November 2026

Shoreline Sightseeing is seeking experienced and safety-focused Captains to operate our passenger vessels on the Chicago River and Lake Michigan. Captains are responsible for the safe navigation and operation of vessels while ensuring the security and well-being of both crew members and passengers.In this leadership role, you will oversee vessel operations, guide marine crew, and maintain compliance with all U.S. Coast Guard regulations. Captains play a critical role in delivering safe, smooth, and memorable tours while maintaining Shoreline’s high operational standards.This position requires strong situational awareness, sound judgment, and a commitment to maintaining a professional and safety-first environment on board. *Training will be paid at Captain Training pay rate of $29/hour until signed off.

• Safely navigate and operate Shoreline vessels along the Chicago River and Lake Michigan

• Ensure the safety and security of all passengers and crew members

• Enforce company policies and safety procedures

• Lead and supervise onboard Marine Crew during daily operations

• Conduct emergency drills and provide training for both new and experienced crew members

• Monitor, document, and report incidents or operational concerns when necessary

• Serve as Vessel Security Officer in compliance with U.S. Coast Guard security regulations

• Coordinate with maintenance personnel to address vessel maintenance or operational needs

• Maintain a clean, organized, and well-prepared vessel at all times

• Strong leadership, communication, and decision-making skills

• Commitment to safety, compliance, and professional vessel operations

• Ability to remain calm and effective in high-pressure situations

• Comfortable working outdoors in varying weather conditions

• Ability to stand for extended periods while operating the vessel

• Ability to lift up to 50 lbs and climb ladders or access confined spaces

• Availability during peak tourism periods, including evenings, weekends, and holidays

• Transportation Worker Identification Credential (TWIC)

• Merchant Mariner Credential (MMC)

• U.S. Coast Guard Medical Certificate

• Marine Radio Operator Permit (MROP)

• CPR / First Aid Certification

Benefits*

• 401k Retirement Plan w/ Employer contributions
• Paid Time Off
• Paid Sick Leave
• Year-round Health Insurance (BCBSIL)
• Dental insurance
• Vision insurance
• Life/Disability Insurance
• Up to $10,000 annual performance/attendance based bonus
  
  *Must be a full-time employee
  
  

Captains play a vital leadership role in one of Chicago’s most iconic waterfront experiences. This position offers the opportunity to operate passenger vessels in a dynamic urban waterway while leading a professional marine crew and delivering safe, memorable experiences for thousands of guests each season.

• Marine Crew (subject to pre-employment and random drug testing in compliance with U.S. Coast Guard regulations)

  • Deckhands

  • Bartenders

• Sales Team Members

• Docents (Tour Guides)

If you’re an experienced mariner who values leadership, safety, and professionalism, we invite you to join our Marine Operations team.

Apply today and become a Captain with Shoreline Sightseeing for the 2026 season!