Job Posting: Pirate Captain 

Company Name: Art & Water Cultural Group / A Pirate’s Life Inc.
Location: Toronto, Barrie, Otawa & Hamilton
Position Type: Temporary, Seasonal (April 1, 2025 - November 30, 2025)
Wage: Beginning at $17.20 per hour, will increase to $18.00 upon completion of all training+ End of Season Tip Share ($1.50 - $4 per hour)
Additional Benefits: Stipend for costume purchase, provided SVOP, SDV-BS, ROC-M and Marine First Aid Training. 

Hours of Work: 

  • Training and Rehearsals will take place during the months of April and May and equal approximately 40-50 hours. 

  • 10 - 20 per week May/June

  • 30 - 40 hours per week July/August

  • 10 - 30 hours per week September/October

  • Regular Shifts:

    • Daytime shifts: 5-8 hours between 8:00 AM and 6:00 PM

    • Evening shifts: 5-8 hours between 4:00 PM and midnight

  • Occasional Shifts:

    • Tour / Private Sail Program Shifts : Minimum 3 hours between 8:00AM and midnight

  • Occasional holiday shifts (including Mondays)

  • Days of Work:

    • May, June, September and October Daytime Shifts occur on Saturdays and Sundays

    • July and August, Daytime Shifts occur between Tuesdays-Sundays

    • May and June, Evening Shifts occur Friday-Sundays

    • July and August, Evening Shifts occur between Thursdays-Sundays

    • September and October, Evening shifts occur between Wednesday-Sunday 

    • Occasional shifts can occur any day of the week 

Availability: 

  1. At the time of interviews, Contractors must provide their availability for the season:

  • July and August: A minimum of 30–40 hours per week during standard daytime and evening shifts.

  • May, June, September, and October: A minimum of 10–20 hours per weekend during standard daytime and evening shifts.

    • The availability provided during auditions will set the Contractor's expected workdays for the season. Hiring decisions will be based on this availability and the altering of this availability may result in termination or renegotiation of contract. 

About Us:
 Art & Water Cultural Group is a registered charity, and A Pirate’s Life Inc. is a dynamic entertainment company specializing in interactive, pirate-themed performances and events. We’re looking for energetic and dedicated Entertainers to join our talented crew for a fun and adventurous season. If you love performing, engaging with audiences, and bringing characters to life, this is the job for you!

Job Description:

As Captain, you will bring the exciting world of pirates to life as part of our entertaining, high-energy shows! You’ll engage with guests, and be an integral part of the experience both on-site and at off-site events. You will lead and navigate our vessel while ensuring the safety, engagement, and enjoyment of all aboard. Oversee crew operations, enforce safety protocols, and deliver an immersive experience for guests!

Captain Key Responsibilities:

  • Vessel Operation: Ensure the safe navigation of the vessel, communicating with other vessels via VHF radio.

  • Passenger & Crew Safety: Oversee the safe conduct of passengers and crew while adhering to Transport Canada safety standards.

  • Maintenance: Complete minor maintenance and repairs of the vessel, and report major issues to management.

  • Safety Oversight: Ensure crew members are safety-trained at the beginning of each shift.

  • Decision-Making: Assess weather conditions for sailing safety, deciding when to proceed or cancel based on forecasts.

  • Communication: Keep in contact with other Ship Captains regarding docking procedures, route optimization, and maintenance updates.

  • Crew Support: Support dingy operators with repairs and other tasks beyond their scope. Provide feedback to entertainers after shows, including notes on performance.

  • General Management: Inform management of any safety or operational issues as they arise.

Skills & Qualifications:

  • Strong performance and improvisational skills, with the ability to engage and entertain audiences of all ages.

  • Comfortable working in an outdoor environment.

  • Excellent communication and interpersonal skills.

  • Reliable, punctual, and able to work flexible hours, including weekends and some holidays.

  • Ability to maintain safety protocols and ensure a positive guest experience.

  • Must complete training in vessel safety and operations (PCOC, SDV-BS, SVOP, ROC(M), Marine First Aid + CPR/AED).

  • Ability to manage crew, monitor safety, and solve operational issues.

  • Ability to assess and respond to weather conditions promptly

  • Previous experience in live entertainment, boating or customer service is a plus, but not required.

  • Willingness to work in costume and engage in fun, interactive activities.

How to Apply:
 If you’re ready to join our team of pirates, apply today! Please send your resume and a brief cover letter highlighting your interest in the position and any relevant experience to work@piratelife.ca

Join the crew at Art & Water Cultural Group / A Pirate’s Life Inc., where every day is a new adventure!