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Sailing Charter Crew Jobs (NOW HIRING)

Captain

HI ยท On-site

$25 - $30/hr

Join the Crew of Maui's Most Luxurious Vessels Ali'i Class Yachts and RED Hospitality are now ... Master 100 Ton Near Coastal with Sailing Endorsement (required for Ali'i Nui) * Master 50 Ton Near ...

Join the Crew of Maui's Most Luxurious Vessels Ali'i Class Yachts and RED Hospitality are now ... Master 100 Ton Near Coastal with Sailing Endorsement (required for Ali'i Nui) * Master 50 Ton Near ...

Catamaran Crew

Key West, FL ยท On-site

$99.99 - $100/hr

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

Catamaran Crew

VI ยท On-site

$99.99 - $100/hr

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

Catamaran Crew

Key West, FL ยท On-site

$85/hr

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

Minimum 5 years of luxury yachting or commercial watersports aboard sailing catamarans in excess of ... Previous day charter experience is a plus * Knowledge of local destinations * Basic knowledge of ...

... Crew, and Customers. Position Summary The Vessel Manager is responsible for planning, directing ... This role works closely with shore-based leadership, vessel crews, charter clients, and internal ...

... Crew, and Customers. Position Summary The Vessel Manager is responsible for planning, directing ... This role works closely with shore-based leadership, vessel crews, charter clients, and internal ...

... Crew, and Customers. Position Summary The Vessel Manager is responsible for planning, directing ... This role works closely with shore-based leadership, vessel crews, charter clients, and internal ...

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Infographic showing various Sailing Charter Crew job openings in the United States as of August 2026, with employment types broken down into 81% Full Time, 18% Part Time, and 1% Contract. Highlights an 99% Physical, and 1% Remote job distribution.

U.S. Captain & Chef/Mate: Charter Yacht Team

Saint Thomas, VI โ€ข On-site

Contractor

Re-posted 26 days ago


Job description


We are Paradise Yacht Management (PYM), the largest exclusively crewed term charter yacht management company in the Caribbean strategically based in St. Thomas, U.S. Virgin Islands. Currently, we have over charter yachts available for a qualified team (Captain and Chef) to crew for the current and upcoming season.
This is a great opportunity for an established Captain and Crew to join PYM in the Virgin Islands term charter industry.This position to show guests a vacation of a lifetime while living aboard a luxurious yacht, and experience unparalleled family-style company culture.
If you have the requirements, please click "I'm Interested" at the top of this page:PYM_Careersto submit your resumรฉ/CV
Paradise Yacht Management is an Equal Opportunity Employer
Compensation:
Salary:Dependent on experience + Tips
Supplemental Pay:Seasonal Bonus Pay, Charter Gratuity/Tips (15-20% of charter rate is standard)
Expected start date:TBD
Requirements
Requirements:
  • Able to work 10 Months (Oct 15th. - August 15th is the season) in St. Thomas, USVI & the BVI.
  • Captain - Active USCG 50T/100T w/ sailing endorsement or RYA License w/commercial endorsement
  • Chef - Culinary / Cooking experience
  • STCW Certifications
  • US Citizen or US Green Card
    Fun, professional attitude & live our company core values (Honor, Integrity, Seek Knowledge, & Have Fun)

Preferences:
  • Familiar with the "Term Yacht Charter Industry"
  • Yachting, cruising and/or sailing experience (for Chef)
  • Service / hospitality experience
  • Mate duties assisting in anchoring docking and other related yacht experience (for Chef)
  • Administrative record keeping and social media experience

Contract length: 10 months (Annual with 10 months-On and 2 months-Off)
Job Types: Full-time, Contract
Benefits
Other Benefits and Cost Savings:
  • Live aboard (no rentor utilities cost)
  • Food and Beveragecost savings while on charter.
  • Adopt the islandcruiser lifestyle and explore the local areas when not on charter