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Sailing Expedition Jobs (NOW HIRING)

SailFuture

Senior Educator

Saint Petersburg, FL · On-site

$60K - $70K/yr

Every student participates in a 7-week international rite-of-passage sailing expedition onboard a 100' school ship. Senior Educator The Senior Educator is a leadership position for an experienced ...

SailFuture

Senior Educator

Saint Petersburg, FL

$60K - $70K/yr

Every student participates in a 7-week international rite-of-passage sailing expedition onboard a 100' school ship. Senior Educator The Senior Educator is a leadership position for an experienced ...

SailFuture

Mental Health Counselor

Saint Petersburg, FL · On-site

$44K - $55K/yr

Finally, you will lead the mental health curriculum during international sailing expeditions, flying in and out ports while students sail from Florida to Nova Scotia and Florida to Trinidad and ...

SailFuture

Business Manager

Saint Petersburg, FL · On-site

$65K/yr

... sailing expeditions. Our model blends high accountability, real-world learning, and relationship-driven support to create durable life outcomes for young people. We operate with urgency ...

SailFuture

Business Manager

Saint Petersburg, FL

$65K/yr

... sailing expeditions. Our model blends high accountability, real-world learning, and relationship-driven support to create durable life outcomes for young people. We operate with urgency ...

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Sailing Expedition information

What are common day-to-day responsibilities when working as part of a sailing expedition team?

Day-to-day responsibilities on a sailing expedition often include operating and maintaining the vessel, assisting with navigation, monitoring weather conditions, and ensuring safety protocols are followed at all times. Team members may also handle sail adjustments, manage onboard equipment and supplies, and assist with meal preparation and cleaning. Collaboration is crucial, as crew members work closely together to respond quickly to changing conditions and emergencies. Additionally, roles can vary depending on the expedition's size and purpose, with opportunities to take on specialized tasks such as scientific data collection or guest management. Each day presents new challenges and learning opportunities, making adaptability and teamwork essential for success.

What are the key skills and qualifications needed to thrive in the Sailing Expedition position, and why are they important?

To excel in a Sailing Expedition role, you need strong seamanship, navigation skills, and a solid understanding of maritime safety protocols, often supported by a relevant boating license such as a U.S. Coast Guard Captain's License or equivalent. Familiarity with navigation software, weather tracking systems, and radio communication devices is essential. Leadership, teamwork, adaptability, and problem-solving abilities help individuals handle the dynamic and sometimes challenging conditions on open water. These skills and qualities are vital for ensuring the safety, efficiency, and success of the expedition, especially in unpredictable environments.

What is a Sailing Expedition job?

A Sailing Expedition job involves leading or assisting in multi-day sailing journeys, often for exploration, adventure, research, or tourism. Responsibilities may include navigation, boat maintenance, safety management, and guiding participants. Depending on the expedition's purpose, roles can range from skipper and crew to marine biologist or expedition guide. Experience with sailing, first aid, and problem-solving in remote locations is typically required.

More about Sailing Expedition jobs
What are the most commonly searched types of Sailing Expedition jobs? The most popular types of Sailing Expedition jobs are:
What job categories do people searching Sailing Expedition jobs look for? The top searched job categories for Sailing Expedition jobs are:
Sailing Expedition jobs near you
Infographic showing various Sailing Expedition job openings in the United States as of July 2026, with employment types broken down into 91% Full Time, and 9% Contract. Highlights an 100% In-person job distribution.
Sailing Yacht Apprenticeship

Sailing Yacht Apprenticeship

SailFuture

Saint Petersburg, FL

$2.0K/mo

Full-time

Medical, PTO

Posted 29 days ago

Job description

About the Apprenticeship
The Yacht Apprenticeship is designed for young adults interested in pursuing a career in the maritime industry. The 12-month apprenticeship will take you around the world, exploring the Americas and the Caribbean.
You will learn and train under experienced mariners while earning sea time towards professional credentials, such as your USCG Captain’s License, Engineering certification, and STCW. At the end of the apprenticeship, SailFuture will provide a stipend to cover the costs of your training classes and exams.
Apprentices reside on the vessel year-round in shared crew quarters with a shared bathroom. Apprentices receive 15 days of paid leave throughout the year.
Apprentices work directly under the Captain, learning all aspects of ship operations and managing complex systems, such as air conditioning, refrigeration, mechanical, electrical, hydraulics, running rigging, etc.
Day to day life revolves around the ship schedule and includes both responsibilities to the ship and program operations, such as education, diving, and sail training. Apprentices can expect at least one day of shore-side leave per week.

About the Vessel
The SailFuture academy Sailing Yacht is a year-round sailing school vessel operating in the Caribbean in the winter months and New England in the summer months.
The vessel is a 100’ Giorgetti & Magrini ketch-rigged sailing yacht with accommodations for 8 students, 2 apprentices, and 6 staff.
Vessel operations include 7-week sailing expeditions with students from the SailFuture Academy and week-long corporate retreats and private charters with paying clients.
Compensation:

  • $2,000 monthly tax-free monthly stipend
  • Room & Board
  • Group meals
  • International health insurance
  • 15 days paid leave per year, including 1 round trip travel to and from the vessel
  • Payment for STCW classes and certification