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Overnight Caribbean Pilot Jobs (NOW HIRING)

REVA INC

Flight Dispatcher

Fort Lauderdale, FL · On-site

... pilot-in-command and ROC Manager. * Maintain accurate and complete records in flight tracking ... Experience working with handling agents in Latin America, the Caribbean, Europe, or Asia-Pacific.

REVA INC

Flight Dispatcher

Fort Lauderdale, FL · On-site

... pilot-in-command and ROC Manager. * Maintain accurate and complete records in flight tracking ... Experience working with handling agents in Latin America, the Caribbean, Europe, or Asia-Pacific.

All JobsCaribbean Pilot JobsOvernight Caribbean Pilot Jobs

Overnight Caribbean Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do overnight caribbean pilot jobs pay per year?

As of Aug 5, 2026, the average yearly pay for overnight 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 are some unique challenges faced by overnight Caribbean pilots, and how can they prepare for them?

Overnight Caribbean Pilots often face challenges such as navigating unpredictable weather patterns, limited visibility, and fatigue from working irregular hours. To prepare, it's essential to stay updated on weather forecasts, maintain strict adherence to rest regulations, and develop strong night navigation skills. Collaboration with ground crews and other pilots is vital to ensure safety and efficiency during overnight operations. Proactively managing rest, staying current with training, and utilizing advanced navigation technology can help pilots handle these challenges effectively.

What is an overnight Caribbean pilot?

An Overnight Caribbean Pilot is a professional pilot who operates flights that take place overnight, primarily within the Caribbean region. These pilots are responsible for safely transporting passengers or cargo between Caribbean islands or from the Caribbean to other destinations during nighttime hours. The role requires advanced navigation skills, knowledge of regional weather patterns, and the ability to operate aircraft under varying conditions. Overnight Caribbean Pilots often work irregular schedules, adapting to time zone changes and ensuring compliance with aviation regulations. Their expertise ensures that flights operate smoothly and safely during less conventional hours.

What is the difference between Overnight Caribbean Pilot vs Caribbean Ferry Captain?

AspectOvernight Caribbean PilotCaribbean Ferry Captain
Required CertificationsCommercial Pilot License, Caribbean maritime certificationsCaptain's License, Coast Guard certifications
Work EnvironmentPrivate or commercial aircraft, overnight flights over Caribbean watersFerry vessels, passenger transport across Caribbean islands
Employer & Industry UsageAirlines, private charters, maritime companiesFerry operators, cruise lines, maritime transport

The Overnight Caribbean Pilot primarily operates aircraft over the Caribbean, requiring pilot licenses and aviation certifications, with a focus on overnight flights. In contrast, the Caribbean Ferry Captain commands passenger vessels, requiring maritime licenses and overseeing ferry routes between islands. Both roles involve navigation and safety in Caribbean waters but differ significantly in their mode of transportation and certification requirements.

What are the key skills and qualifications needed to thrive as an overnight Caribbean pilot?

To thrive as an Overnight Caribbean Pilot, you need a valid commercial pilot’s license, extensive flight hours, strong knowledge of Caribbean airspace, and instrument flight proficiency. Familiarity with aviation navigation systems, GPS, weather radar, and flight management systems is crucial, along with any required regional certifications. Excellent decision-making, situational awareness, and effective communication are essential soft skills, especially given the challenges of night flying and remote destinations. These competencies ensure safe, efficient, and reliable flight operations in sometimes unpredictable Caribbean conditions.
More about Overnight Caribbean Pilot jobs
What cities are hiring for Overnight Caribbean Pilot jobs? Cities with the most Overnight 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 Overnight Caribbean Pilot jobs? States with the most job openings for Overnight Caribbean Pilot jobs include:
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Overnight Caribbean Pilot jobs near you
Infographic showing various Overnight Caribbean Pilot job openings in the United States as of July 2026, with employment types broken down into 2% Locum Tenens, 2% As Needed, 82% Full Time, 12% Part Time, and 2% Contract. 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.

Corporate Pilot/Co-Pilot - Whittier Health Network

Whittier Health Network

Haverhill, MA • On-site

Part-time

Re-posted 24 days ago

Job description

Whittier Health Network - Corporate Offices
Corporate Pilot - Citation CJ3 Co-Pilot
Must live in New England USA - Lawrence Massachusetts area preferred
Privately owned Citation CJ3 based at Lawrence Municipal Airport (KLWM) is seeking a professional, experienced pilot for part-time flying and operational support in a well-maintained Part 91 operation.
This position is ideal for a retired or semi-retired airline captain, experienced corporate pilot, or current turbine pilot seeking flexible supplemental flying with a professional owner-operated flight department.
Primary flying includes Northeast, Florida and Caribbean operations.
Aircraft:
  • Cessna Citation CJ3
  • Based at Lawrence Municipal Airport (KLWM) - Massachusetts
Preferred Qualifications:
  • CE-525 type rating strongly preferred
  • Single-pilot CE-5255 qualification a plus
  • Prior airline captain or significant turbine PIC experience preferred
  • 5,000+ total flight hours
  • Strong turbojet experience
  • Professional cockpit demeanor and sound operational judgment
  • Ability to work well in a flexible owner-operated environment
  • Availability for occasional overnight and multi-day trips
Responsibilities:
  • Assist in all phases of flight operations
  • Support safe, efficient Part 91 flight operations
  • Coordinate flight preparation, charts, manuals, and aircraft readiness
  • Assist with aircraft operational readiness, avionics/database updates, and hangar coordination
  • Maintain high standards of professionalism and aircraft presentation
  • Work closely with owner/pilot in a team-oriented environment
Ideal Candidate:
We are particularly interested in candidates with strong airline or corporate turbine backgrounds who value professionalism, flexibility, safety, and long-term working relationships over high-volume flying schedules.
Compensation:
Flexible compensation structure designed to provide consistency and fairness, including compensation for both operational support and flight responsibilities. Terms based on experience, qualifications, and availability.
Located in Lawrence Mass area preferred, but not required.

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