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Fleet Captain, Leader & Sailing Instructor

Summer 2026 — Toronto, ON

Duration: 12 weeks (mid-June to late August 2026)
Hours: 30 hours/week
Wage: $65.00/hour
Location: Toronto (Lakeshore area and multiple marina/sailing club sites)

We’re looking for an experienced mariner to lead and instruct all on-water programming for Ships2Shores. This is the senior sailing role for the season, responsible for the safety, seamanship, and spirit of everything that happens on the water.

What You’ll Do

• Lead and instruct participants in all aspects of sailing and sail training
• Ensure all vessels are seaworthy, properly maintained, and safety-equipped throughout the season
• Deliver on-shore instruction in sailing fundamentals, safety, and fitness preparation
• Oversee crew and volunteer sailing staff, providing guidance and direction
• Monitor all on-water and on-shore activities to ensure participant safety
• Provide emergency response and first aid when required
• Maintain records of vessel maintenance, safety checks, and incident reports

What We’re Looking For

• Sail Canada Cruising Intermediate certification (minimum) and 1,000+ logged nautical miles
• Pleasure Craft Operator Card, VHF Radio Operator Certificate, and Harbour License
• Standard First Aid & CPR certification
• Demonstrated experience in fleet maintenance, vessel care, and overseeing crew
• Proven ability to instruct youth or young adults in sailing
• Strong situational awareness and sound judgment on the water
• A valid Vulnerable Sector Check (required prior to first day)

Apply: Send your resume and a brief cover letter to [email protected] with the subject line “Fleet Captain Application.”

 📄 See the  full posting (PDF)

Contract Boat Staff

Ships2Shores — Summer 2026 — Toronto, ON

Duration: Seasonal (mid-June to late August 2026)
Hours: Up to 155 hours
Wage: $39.00/hour
Location: Toronto (various sailing club sites)

We’re looking for three Contract Boat Staff to support the Fleet Captain and work directly alongside participants on the boats, on the docks, and during ashore activities. You’ll be a steady, encouraging presence helping young people build confidence on the water.

What You’ll Do

• Support the Fleet Captain in all aspects of sail training and participant supervision
• Maintain a continuous, vigilant presence on board to ensure participant safety
• Monitor weather, water, and vessel conditions and communicate concerns to the Fleet Captain
• Help deliver on-shore activities including safety training and fitness preparation
• Provide first aid and emergency response when required
• Assume interim command of a vessel if the Fleet Captain is incapacitated or unavailable
• Complete participant oversight logs, incident reports, and program reporting
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What We’re Looking For

• Pleasure Craft Operator Card (required)
• Standard First Aid & CPR certification (required)
• VHF Radio Operator Certificate (strongly preferred)
• Sail Canada certification (any level) is an asset
• Demonstrated on-water sailing experience
• Experience working with youth or young adults in a supervisory or mentorship capacity
• Calm, clear-headed, and decisive under pressure
• A valid Vulnerable Sector Check (required prior to first day)

Apply: Send your resume and a brief cover letter to [email protected] with the subject line “Boat Staff Application.”

📄 See the full posting (PDF)