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Boat Captain (Caribbean)

SailFuture Academy

St. Petersburg, Florida, US$90kPosted Oct 1, 2026

Job description

Seeking an experienced offshore Captain for rotational position on a 100’ school ship serving at-risk youth. $7,500 per month + Bonus based on program outcomes. The vessel operates primarily in the Caribbean between Trinidad and St. Maarten. Schedule Rotational Captains work 1 to 3 Expeditions per year. Each Expedition is 9 weeks in length.

(1) week for prep, (7) weeks with students, and (1) week for wrap-up and handoff. Vessel The vessel is a 100’ Giorgetti & Magrini ketch-rigged sailing yacht with accommodations for 12 students and 6 staff. Staff quarters are separate from students and are in shared cabins with a shared bathroom.

Responsibilities

Overall management and upkeep of the vessel Perform daily, weekly, monthly, and annual maintenance on all systems Diagnose and repair all systems as needed Ensure that program Standard Operating Procedures are followed at all times Build strong bonds with each youth through 1:1 and group time Build a strong sense of teamwork amongst youth and staff on the boat Hold all youth and rotating program staff to the highest levels of seamanship Participate in service learning projects and all youth programming throughout the expedition Other duties as assigned Minimum Qualifications USCG 100-Ton Master, RYA Yachtmaster Offshore, or IYT Yachtmaster offshore 5+ years as Captain / Master of a sailing vessel > 65’ LOA Strong knowledge of all yacht systems Valid driver’s license Empathy to relate to the life experiences of the youth Sail.

Future serves First Aid / CPR / Lifeguard certifications Compensation $7,500 per month $2,500 bonus per term based on Impact Outcomes Flights to and from the vessel (up to $750 round trip) Geo. Blue health insurance while on the vessel

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