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Pilot In The Caribbean Jobs (NOW HIRING)

Seaborne Airlines

DHC6 Pilot

Saint Croix, VI · On-site

$75/hr

Twin Engine Seaplane Pilot - FAA Part 121 Operations (Caribbean) Location: Caribbean Base - St ... Experience operating in the Caribbean or other tropical maritime environments * Familiarity with ...

NetJets & EJM

Pilot in Command Hawker 4000

Englewood, CO · On-site

$200K - $220K/yr

Simons GA, Teterboro, and occasional flights to the Caribbean. This is your chance to join a Part ... Pilot in Command: 2000 hours * PIC MEL: 500 hours * Instrument: 300 hours * Jet: 500 hours

Jet Linx

PIC - Gulfstream G200 Floater

Omaha, NE

$195K - $251K/yr

Position Summary The Pilot in Command (PIC) reports directly to the Base Chief Pilot. The PIC ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Priority-1, Inc.

Pilot in Command

Little Rock, AR · On-site

$150 - $180/hr

## Pilot in CommandApplylocations: Little Rock, ARtime type: Full timeposted on: Posted 2 Days Agojob ... Our mission is to be the innovator and leader in establishing customers, employees, and vendors by ...

Jet Linx Aviation

PIC - Gulfstream G200 Floater

Omaha, NE · On-site

$195K - $251K/yr

Position Summary The Pilot in Command (PIC) reports directly to the Base Chief Pilot. The PIC ... Unrestricted ability to travel to Canada and Caribbean countries * Ability to pass a pre-employment ...

Intermountain Health

Pilot In Command

Neenah, WI · On-site

$45.55 - $71.73/hr

As an Air Ambulance Pilot, you are the critical link in delivering rapid, life-saving transportation for patients in need. Your expertise ensures the safety of the medical team and patients during ...

MAVERICK HELICOPTERS

Pilot In Command

Henderson, NV

Maverick Helicopters, the largest operator of EC130 in the world, is currently seeking applicants to full full time Tour Pilot positions. Maverick Helicopters prides itself in being a leader in the ...

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All JobsPilot In The Caribbean Jobs

Pilot In The Caribbean information

See salary details

$49.5K

$130.9K

$201K

How much do pilot in the caribbean jobs pay per year?

As of Jul 26, 2026, the average yearly pay for pilot in the caribbean 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 is the difference between Pilot In The Caribbean vs Commercial Pilot?

AspectPilot In The CaribbeanCommercial Pilot
Required CertificationsCommercial Pilot License (CPL), specific regional certificationsCommercial Pilot License (CPL), often with additional ratings
Work EnvironmentRegional airlines, charter services, private flights in Caribbean regionVarious, including cargo, passenger, and charter flights globally
Employer & Industry UsageRegional airlines, private operators in CaribbeanAirlines, cargo companies, private operators worldwide

The main difference between a Pilot In The Caribbean and a Commercial Pilot lies in their operational scope and regional focus. A Pilot In The Caribbean typically operates within the Caribbean region, often for regional airlines or private charters, requiring specific certifications. A Commercial Pilot, on the other hand, can work in a broader range of industries globally, with similar licensing requirements but often with additional ratings for different aircraft types and operations.

More about Pilot In The Caribbean jobs
What cities are hiring for Pilot In The Caribbean jobs? Cities with the most Pilot In The Caribbean job openings:
What states have the most Pilot In The Caribbean jobs? States with the most job openings for Pilot In The Caribbean jobs include:
What job categories do people searching Pilot In The Caribbean jobs look for? The top searched job categories for Pilot In The Caribbean jobs are:
Pilot In The Caribbean jobs near you
Infographic showing various Pilot In The Caribbean job openings in the United States as of July 2026, with employment types broken down into 57% Locum Tenens, 1% As Needed, 32% Full Time, 5% Part Time, 1% Contract, and 4% Summer. Highlights an 94% Physical, 1% Hybrid, and 5% Remote job distribution, with an average salary of $130,916 per year, or $62.9 per hour.
Northeast Regional Chief Pilot

Northeast Regional Chief Pilot

Tradewind Aviation

East White Plains, NY • On-site

$155K - $200K/yr

Full-time

Medical, Retirement, PTO

Posted 24 days ago

Job description

Job Type
Full-time
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.

Tradewind Aviation offers a competitive pay and benefits program for full-time team members:
  • Comprehensive health and voluntary insurance plans
  • Retirement plan with company match
  • Paid time off
  • Standby travel on select Tradewind Aviation scheduled flights
  • Discounted standby travel benefits on numerous major and regional US and international airlines
  • A rewarding career path with opportunities for growth and advancement throughout the organization

Salary Range:
$155k-$200k a year

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