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Caribbean Pilot Jobs (NOW HIRING)

Jet Linx Aviation

$195K - $251K/yr

Description Pilot in Command - Falcon 900EX Full-Time - Commutable, USA Jet Linx is seeking ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Jet Linx

$195K - $251K/yr

Pilot in Command - Falcon 900EX Full-Time - Commutable, USA Jet Linx is seeking qualified Pilot in ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Jet Linx

PIC - Citation XLS/XLS+ Floater

Omaha, NE

$145K - $200K/yr

Pilot in Command - Citation XLS/XLS+ Full-Time - Commutable, USA Jet Linx is seeking qualified ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Jet Linx Aviation

PIC - Citation XLS/XLS+ Floater

Omaha, NE · On-site

$145K - $200K/yr

Pilot in Command - Citation XLS/XLS+ Full-Time - Commutable, USA Jet Linx is seeking qualified ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Jet Linx Aviation

PIC - Citation XLS/XLS+ Floater

Omaha, NE · On-site

$145K - $200K/yr

Description Pilot in Command - Citation XLS/XLS+ Full-Time - Commutable, USA Jet Linx is seeking ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Jet Linx Aviation

PIC - Gulfstream G200

Houston, TX · On-site

$160K - $245K/yr

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

Jet Linx

PIC - Gulfstream G200

Dallas, TX

$160K - $245K/yr

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

Jet Linx

PIC - Gulfstream G200

Houston, TX

$160K - $245K/yr

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

Jet Linx Aviation

PIC - Gulfstream G200

Austin, TX · On-site

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

Jet Linx

PIC - Citation Sovereign

Saint Louis, MO

$160K - $245K/yr

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

Jet Linx Aviation

PIC - Citation Sovereign

Saint Louis, MO · On-site

$160K - $245K/yr

Unrestricted ability to travel to all EU, Canada, and Caribbean countries * Ability to release and pass a FAA Pilot Record Database review with a System Chief Pilot * Ability to work nights, weekends ...

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All JobsCaribbean Pilot Jobs

Caribbean Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do caribbean pilot jobs pay per year?

As of Jul 14, 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.

More about Caribbean Pilot jobs
What cities are hiring for Caribbean Pilot jobs? Cities with the most Caribbean Pilot job openings:
What are the most commonly searched types of Caribbean Pilot jobs? The most popular types of Caribbean Pilot jobs are:
What states have the most Caribbean Pilot jobs? States with the most job openings for Caribbean Pilot jobs include:
What job categories do people searching Caribbean Pilot jobs look for? The top searched job categories for Caribbean Pilot jobs are:
Caribbean Pilot jobs near you
Infographic showing various Caribbean Pilot job openings in the United States as of July 2026, with employment types broken down into 91% Full Time, 6% Part Time, and 3% Contract. Highlights an 94% In-person, 3% Hybrid, and 3% Remote job distribution, with an average salary of $130,916 per year, or $62.9 per hour.

Pilot in Command Challenger CL300

NetJets & EJM

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 12 days ago

Job description

About EJM
EJM has been a pioneer in aircraft management and worldwide jet charter services since 1977. As a subsidiary of NetJets, we are part of the world's largest private aviation infrastructure, with unrivaled resources and operational stability. Our business is rooted in the core principles of safety, service, and integrity-principles that we deliver on daily for our customers and employees.
Purpose of Position
Executive Jet Management, a Berkshire Hathaway company, is seeking qualified Pilot in Command candidates for a Challenger CL300 aircraft based in Chicago IL at MDW airport. This is a three-pilot account supported by a dedicated Maintenance Technician flying owner part 135 and part 91. Flying is mostly domestic with a few international trips annually to the Caribbean and Mexico for an average of 200 hours of total annual flying.
This position is not commutable and will require residing within a one-hour driving distance to MDW airport.
Tasks and Responsibilities
Ensures the Safe Operation of Flight:
  • Ensures crewing and trip assignments are compliant with company and regulatory requirements.
  • Completes flight planning, performance and weight and balance tasks for each assignment, as required.
  • Utilizes Threats, Plans and Considerations (TPC) briefing methodology to lead required briefings and mitigate operational risks.
  • Complies with company Standard Operating Procedures (SOPs) and coordinates with company personnel as required. Acts as the Grounds Security and In-Flight Security Coordinator as defined by company policy.
  • Completes all aircraft pre-flight tasks, including the maintenance status of the aircraft, to ensure the aircraft is mission capable. Records all aircraft discrepancies in accordance with company SOPs.
  • Ensures all aircraft ground servicing items (e.g., fueling, oil, oxygen) are monitored and accomplished in accordance with SOPs.
  • Completes passenger briefings in accordance with company policy and regulation. Delivers the highest level of customer service and meet any special needs of passengers (e.g., physically challenged).
  • Utilizes Crew Resource Management (CRM) and Threat and Error Management (TEM) to communicate with crew and support personnel clearly and in a timely manner during normal, abnormal, and emergency operations.

Delivers an Exceptional Service Experience:
  • Provides quality service to owners and passengers while identifying opportunities to enhance the EJM service experience. Regularly investigates and resolves service deviations.
  • Collaborates with fellow crew members and EJM internal partners to provide consistent service experience to owners and passengers. Resolves conflict and challenges in an acceptable manner.

Maintains Proficiency and Compliance:
  • Maintains regulatory and company-required training and recency of experience.
  • Complies with company SMS program and reports safety or non-compliance concerns through the appropriate channels.

Note:
It is not possible to list all required job duties on this form. There may be other important duties assigned, depending on the position. For a list of essential job functions, please refer to the essential functions document for this job.
Certifications and Licenses
FAA Airline Transport Pilot (ATP)
First Class Medical Certificate
Years of Experience
4-6 years of experience
Knowledge, Skills, Abilities and Other (KSAOs)
  • Prior experience in corporate/business aviation preferred
  • FAA Type rating in applicable fleet
  • Must be able to perform the essential functions of the position
  • Minimum Time Requirements:
    • Total flight time: 3500 hours
    • Multi Engine Land (MEL): 1500 hours
    • Pilot in Command: 2000 hours
    • PIC MEL: 500 hours
    • Instrument: 300 hours
    • Jet: 500 hours

How EJM Supports You
At EJM, we believe that how you do something is as important as what you do. That's why we foster a collaborative company culture, where leadership is accessible, employee opinions are valued, and relationships matter. We encourage employee growth, recognize the importance of work-life balance, and take pride in being a career destination.
To ensure our employees are taken care of at work and at home, we offer a comprehensive package of premium benefits, including:
  • Competitive pay
  • Medical, dental, and vision insurance, available with no monthly premiums
  • 401(k) plan, with 67% of every dollar you contribute matched by EJM
  • Health savings account (HSA)
  • Flexible spending accounts (FSA)
  • Prescription drug benefit plan
  • Life insurance and AD&D benefits
  • Short-term disability
  • Long-term disability
  • Loss of license coverage
  • Paid Parental Leave
  • Pet insurance
  • 14 days of paid time off, available on first day of employment

Executive Jet Management is an equal opportunity employer.
To ensure a safe environment, we conduct pre-employment drug screening and background checks.

Apply