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Caribbean Pilot Jobs (NOW HIRING)

Tradewind

Northeast Regional Chief Pilot

Oxford, CT · On-site

About the Candidate / Role Tradewind Aviation is seeking dedicated and experienced Regional Chief Pilots to support our Northeast (HPN), Southeast (SUA) and Caribbean (SJU) operations. This role is ...

Tradewind

Southeast Regional Chief Pilot

Oxford, CT · On-site

... Caribbean. For more details visit www.flytradewind.com About the Role / Candidate Tradewind Aviation is seeking dedicated and experienced Regional Chief Pilots to support our Northeast (HPN ...

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Caribbean Pilot information

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$49.5K

$130.9K

$201K

How much do caribbean pilot jobs pay per year?

As of Jun 9, 2026, the average yearly pay for caribbean pilot in the United States is $130,916.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,000.00 and $155,000.00 per year, depending on experience, location, and employer.

What Does a Caribbean Pilot Do?

As a Caribbean pilot, your job is to fly an airplane to and from areas like the Bahamas. Some Caribbean pilots focus exclusively on this region, while other pilots bring passengers to different international destinations as well. In this aviation role, you study weather patterns to determine the advisability of flight routes, communicate any required changes, and guide the crew. Many Caribbean pilots specialize in specific types of planes or passengers. For example, you may work exclusively for a single business to fly its personnel or follow the directions of a dispatcher to provide emergency medical transportation between islands. Caribbean pilots are often members of AOPA and stay involved with aviation activities, but this is not mandatory for the job.

What is a Caribbean Pilot job?

A Caribbean Pilot is a highly trained maritime professional responsible for navigating ships safely through Caribbean waters, particularly in and out of ports, harbors, and challenging coastal areas. They have expert knowledge of local waterways, tides, and weather conditions to prevent accidents and ensure efficient maritime operations. Pilots typically board vessels to assist captains with precise maneuvering, working closely with port authorities and ship crews.

What are some common challenges faced by Caribbean Pilots on the job?

Caribbean Pilots often encounter challenges such as rapidly changing weather conditions, navigating shallow or reef-filled waters, and guiding vessels of varying sizes into busy or less-developed ports. They must remain alert to shifting currents, local maritime regulations, and the presence of other marine traffic. Effective communication with diverse ship crews and local authorities is key, as well as staying updated on port-specific protocols. Despite the demanding environment, the role offers deep professional satisfaction and a strong sense of responsibility in ensuring maritime safety.

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

To thrive as a Caribbean Pilot, you need advanced navigational skills, in-depth maritime knowledge, and appropriate licensure such as a pilot’s license issued by the relevant maritime authority. Expertise with vessel traffic management systems, radar equipment, and up-to-date navigational charts is crucial for this role. Excellent communication, decision-making abilities, and situational awareness help Caribbean Pilots coordinate effectively with ship crews and port authorities. These skills ensure safe and efficient vessel movements through complex and sometimes hazardous Caribbean waters.

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Caribbean Pilot jobs near you
Northeast Regional Chief Pilot

Northeast Regional Chief Pilot

Tradewind

Oxford, CT • On-site

Full-time

Posted 10 days ago

Job description

Description:

About Tradewind

Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel—both private and scheduled service—throughout North America and the Caribbean.

For more details visit www.flytradewind.com



Requirements:

About the Candidate / Role

Tradewind Aviation is seeking dedicated and experienced Regional Chief Pilots to support our Northeast (HPN), Southeast (SUA) and Caribbean (SJU) operations. This role is designed for a proactive aviation leader who thrives in a dynamic environment and is committed to safety, operational excellence, and pilot support.

Base Chief Pilots will work closely with the Chief Pilot and company leadership to support day-to-day flight operations, oversee pilot activity in their assigned region, and ensure compliance with FAA regulations, company policies, and Tradewind’s safety culture.

This is primarily an in-office role, with limited flying responsibilities.


Essential Functions

  • Pilot leadership & oversight
  • Provide direct supervision, guidance, and support to flight crewmembers assigned to the region.
  • Address operational, performance, and safety concerns in a timely and professional manner.
  • Ensure pilots adhere to established company procedures, regulatory requirements, and safety standards.
  • Serve as an accessible leadership presence for pilots, promoting a positive and transparent culture.

Operational Support & Compliance

  • Support the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and all operational standards.
  • Assist in maintaining operational control and facilitating communication between flight crews, Dispatch, and leadership.
  • Monitor crew qualifications, scheduling requirements, and readiness for assigned missions for trip executed in the assigned region.
  • Ensure adherence to the General Operations Manual and other company guidance.

Training & Checking

  • Conduct pilot evaluation, ground and flight training, base-level standardization, and recurrent/proficiency activities as assigned.
  • Support the Director of Operations and Director of Training in evaluating and enhancing training programs.
  • Maintain knowledge of current aviation regulations, company policy changes, and industry best practices, ensuring timely dissemination of relevant updates to flight crews.

Administration & Base Management

  • Serve as the primary liaison for region-specific pilot issues, operational needs, and personnel support.
  • Assist with performance evaluations, coaching, documentation, and follow-up actions.
  • Participate in pilot recruiting, interviewing, and onboarding activities for the assigned region.
  • Coordinate initiatives, pilot meetings, and local operational improvements.

Cross-Functional Collaboration

  • Collaborate closely with the Chief Pilot, SVP of Operations, Director of Operations, Director of Training, and Safety Department to align region activities with company goals.
  • Support safety investigations, corrective action plans, and proactive safety initiatives.

Flying & Operational Duties

  • Perform limited line flying as required, including missions supporting training, checking, and operational continuity.
  • Maintain personal qualifications and currency in accordance with company policies and FAA requirements.

Other Duties

  • Carry out additional assignments as assigned by the Chief Pilot

Qualifications

  • Commercial or ATP certificate with appropriate ratings for company operations.
  • Strong knowledge of FAA Part 135 regulations and operational requirements.
  • Previous experience in pilot leadership, supervision, or pilot development strongly preferred.
  • Excellent communication, interpersonal, and problem-solving skills.
  • Ability to work flexibly, support on-call operational needs, and travel occasionally.
  • Demonstrated commitment to safety, professionalism, and high operational standards.

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