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Sailing Caribbean Jobs (NOW HIRING)

SailFuture

Boat Captain

Saint Petersburg, FL

$7.5K/mo

The vessel operates primarily in the Caribbean between Trinidad and St. Maarten. Schedule ... Vessel The vessel is a 100' Giorgetti & Magrini ketch-rigged sailing yacht with accommodations for ...

SailFuture

Boat Captain

Saint Petersburg, FL · On-site

$76 - $91/hr

The vessel operates primarily in the Caribbean between Trinidad and St. Maarten. Schedule ... Vessel The vessel is a 100' Giorgetti & Magrini ketch-rigged sailing yacht with accommodations for ...

SailFuture

Boat Captain

Saint Petersburg, FL · On-site

$7.5K/mo

The vessel operates primarily in the Caribbean between Trinidad and St. Maarten. Schedule ... Vessel The vessel is a 100' Giorgetti & Magrini ketch-rigged sailing yacht with accommodations for ...

SailFuture

Teacher

Saint Petersburg, FL · On-site

$38K/yr

In addition, we provide challenging, rite-of-passage sailing experiences both domestically and ... Petersburg, Fl and on our sailboat navigating around central America and the Caribbean.

SailFuture

Teacher

Saint Petersburg, FL · On-site

$38K/yr

In addition, we provide challenging, rite-of-passage sailing experiences both domestically and ... Petersburg, Fl and on our sailboat navigating around central America and the Caribbean.

Dream Yacht Worldwide

Be Seen First

Customer Service Specialist

Saint Petersburg, FL · On-site

$41K - $50K/yr

Company Description Dream Yacht Worldwide is the global leader in sailing tourism. Since our ... the Mediterranean, Caribbean, Bahamas, Tahiti, Asia, and beyond. Our Clearwater-based North ...

Dream Yacht Worldwide

Be Seen First

Customer Service Specialist

Tampa, FL · On-site

$41K - $50K/yr

Company Description Dream Yacht Worldwide is the global leader in sailing tourism. Since our ... the Mediterranean, Caribbean, Bahamas, Tahiti, Asia, and beyond. Our Clearwater-based North ...

Dream Yacht Worldwide

Be Seen First

Customer Service Specialist

Clearwater, FL · On-site

$41K - $50K/yr

Company Description Dream Yacht Worldwide is the global leader in sailing tourism. Since our ... the Mediterranean, Caribbean, Bahamas, Tahiti, Asia, and beyond. Our Clearwater-based North ...

Dream Yacht Worldwide

Be Seen First

Customer Service Specialist

Clearwater, FL · On-site

$41K - $50K/yr

Company Description Dream Yacht Worldwide is the global leader in sailing tourism. Since our ... the Mediterranean, Caribbean, Bahamas, Tahiti, Asia, and beyond. Our Clearwater-based North ...

Antillean Line

Ocean Freight Traffic Manager

Miami, FL · On-site

... the Caribbean, including Haiti, the Dominican Republic, Turks & Caicos and the Bahamas. As the ... sailing confirmation. * Make sure all deadlines are met, including document cut-offs, terminal cut ...

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All JobsSports and Recreation JobsSailing Caribbean Jobs

Sailing Caribbean information

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$7

$16

$23

How much do sailing caribbean jobs pay per hour?

As of Aug 26, 2026, the average hourly pay for sailing caribbean in the United States is $16.95, according to ZipRecruiter salary data. Most workers in this role earn between $15.87 and $18.75 per hour, depending on experience, location, and employer.

What is a sailing Caribbean job?

Sailing Caribbean jobs typically involve working on sailing vessels, such as yachts or charter boats, in the Caribbean region. These jobs can include positions like captain, crew member, sailing instructor, or maintenance staff. The roles often involve operating the boat, ensuring passenger safety, teaching sailing skills, and maintaining the vessel. Many positions are seasonal and may require certifications or previous sailing experience. Working in this field offers the opportunity to travel, meet new people, and enjoy life on the water.

What are common challenges faced by crew members working on sailing charters in the Caribbean, and how can they prepare for them?

Crew members on Caribbean sailing charters often encounter challenges such as adapting to changing weather conditions, managing guest expectations, and working in confined spaces for extended periods. Teamwork and clear communication are essential, as crew members must collaborate closely to ensure the safety and enjoyment of guests. Preparing by gaining strong technical sailing skills, developing excellent customer service abilities, and maintaining a flexible, positive attitude will help you thrive in this dynamic work environment.

What are the key skills and qualifications needed to thrive as a Caribbean sailing captain, and why are they important?

To thrive as a Caribbean Sailing Captain, you need a thorough understanding of seamanship, navigation, and maritime safety, typically backed by certifications like the RYA Yachtmaster or a U.S. Coast Guard license. Proficiency with GPS navigation systems, VHF radios, weather forecasting tools, and basic marine engine maintenance is essential. Strong leadership, problem-solving, and effective communication skills help manage crew and ensure guest satisfaction. These competencies are vital to ensure safe voyages, handle emergencies, and provide an enjoyable experience in the challenging and dynamic Caribbean sailing environment.

What is the difference between Sailing Caribbean vs Sailing Instructor?

AspectSailing CaribbeanSailing Instructor
CertificationsRYA certifications, CPR, first aidRYA certifications, CPR, first aid
Work EnvironmentCharter boats, luxury yachts, islandsMarinas, sailing schools, training vessels
Industry UsageCharter companies, tourism, leisure sailingTraining centers, sailing schools, yacht clubs

Both Sailing Caribbean and Sailing Instructor roles require similar certifications like RYA certifications and focus on sailing in maritime environments. However, Sailing Caribbean typically involves working on charter yachts and tourism-focused settings in the Caribbean, while Sailing Instructors primarily teach sailing skills at training centers or sailing schools. The roles overlap in credentials but differ in work environment and job focus.

Infographic showing various Sailing Caribbean job openings in the United States as of August 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 100% In-person job distribution, with an average salary of $35,266 per year, or $17 per hour.

Sailing Yacht Apprenticeship

Saint Petersburg, FL

SailFuture
Civic and Social Organizations • 11 - 50 employees
Learn more about SailFutureexternal

$2.0K/mo

Full-time

Medical, PTO

Re-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