Job Posting: Pirate Entertainment Crew Member

Company Name: Art & Water Cultural Group / A Pirate’s Life Inc.
Location: Toronto, Barrie, Hamilton, Ottawa
Position Type: Temporary, Seasonal (April 1, 2025 - November 30, 2025)
Wage: $17.20 per hour + End of Season Tip Share ($1.50 - $4 per hour)
Additional Benefits: Stipend for costume purchase, training provided

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 auditions, 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 an Entertainer, you will bring the exciting world of pirates to life as part of our entertaining, high-energy shows! You’ll perform live shows, engage with guests, and be an integral part of the experience both on-site and at off-site events. Your role will require a passion for performance, a love for immersive experiences, and the ability to engage guests in memorable ways. If you’re ready to become a pirate and make a lasting impact, we’d love to hear from you!

Key Responsibilities:

  • Performance: Prepare and perform engaging, interactive pirate shows as directed by the Company’s leadership teams.

  • Dinghy Operation: Obtain Pleasure Craft Operators Certification in order to operate our Dinghy in the role of the Villain!

  • Audience Engagement: Stay in character and interact with the audience before, during, and after shows. Participate in shore activities such as face painting, pirate games, and costume engagement.

  • Safety Protocols: Ensure the safety and well-being of all audience members, adhering to company safety guidelines and protocols, and completing bi-weekly safety training.

  • Training & Attendance: Attend all required rehearsals, safety training, and scheduled performances. Notify management of any scheduling conflicts and work to find solutions.

  • Site Maintenance Support: Assist in maintaining the cleanliness of the performance site, including but not limited to taking out trash, sanitizing commonly touched surfaces, and reporting any issues related to props or equipment.

  • Off-Site Events: Perform at off-site locations, such as workshops, festivals, and other events, as needed.

  • Costume: Purchase and wear an approved pirate costume, with a stipend provided to help with the purchase.

  • Front-of-House Support: Assist with guest check-in, responding to customer needs, and selling alcohol as required.

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.

  • Previous experience in live entertainment 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!