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Seasonal Caribbean Pilot Jobs (NOW HIRING)

Tradewind Aviation

Nantucket Concierge

Nantucket, MA · On-site

$17.50 - $22.75/hr

... Caribbean. For more details visit www.flytradewind.com About the Candidate / Role Tradewind ... Collects, organizes, and weighs baggage for pilots. * Ensures passenger comfort and keeps ...

Tradewind

Nantucket Concierge

Nantucket, MA · On-site

$17.50 - $22.75/hr

... Caribbean. For more details visit www.flytradewind.com About the Candidate / Role Tradewind ... Collects, organizes, and weighs baggage for pilots. * Ensures passenger comfort and keeps ...

Tradewind Aviation LLC

Nantucket Concierge

Nantucket, MA · On-site

$17.50 - $22.75/hr

... Caribbean. For more details visit www.flytradewind.com About the Candidate / Role Tradewind ... Collects, organizes, and weighs baggage for pilots. * Ensures passenger comfort and keeps ...

Tradewind Aviation

Martha's Vineyard Concierge

MA · On-site

$17.50 - $22.75/hr

... the Caribbean. For more details visit www.flytradewind.com About the Candidate/Role Tradewind ... Collects, organizes, and weighs baggage for pilots. * Ensures passenger comfort and keeps ...

Tradewind

Martha's Vineyard Concierge

West Tisbury, MA · On-site

$17.50 - $22.75/hr

... the Caribbean. For more details visit www.flytradewind.com About the Candidate/Role Tradewind ... Collects, organizes, and weighs baggage for pilots. * Ensures passenger comfort and keeps ...

Benchmark

Line Cook

Lodge, SC · On-site

$13.50 - $17/hr

... Caribbean, and Europe. Our platform includes Benchmark Resorts & Hotels, a collection of ... The Lodge will play host JetBlue's new-hire orientation and training; on-going pilot, crew and ...

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Seasonal Caribbean Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do seasonal caribbean pilot jobs pay per year?

As of Aug 24, 2026, the average yearly pay for seasonal 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 is a seasonal Caribbean pilot?

Seasonal Caribbean Pilots are maritime professionals who guide ships through the complex and often challenging waters of the Caribbean region, typically during peak shipping or cruise seasons. Their main role is to ensure the safe navigation of vessels, using their extensive local knowledge of tides, currents, weather, and hazards. Many ports require the use of a pilot to prevent accidents and protect sensitive marine environments. Seasonal pilots may work only during the busiest months or when traffic increases due to tourism or trade.

What skills and qualifications are needed to be a seasonal Caribbean pilot?

To thrive as a Seasonal Caribbean Pilot, you need a valid commercial pilot license, extensive flight experience in the region, and strong knowledge of Caribbean aviation regulations and weather patterns. Familiarity with navigation systems, GPS technology, and aircraft commonly used for island-hopping is essential, along with any required regional endorsements. Exceptional situational awareness, adaptability, and clear communication skills set outstanding pilots apart, especially when dealing with variable weather and island-specific challenges. These skills ensure safe, efficient flight operations and the ability to respond effectively to dynamic conditions typical of Caribbean routes.

What unique challenges might a seasonal Caribbean pilot face during the busy tourist season?

Seasonal Caribbean Pilots often encounter increased air traffic, rapidly changing weather conditions, and diverse international passenger expectations during peak tourist months. Navigating frequent takeoffs and landings between island airports requires strong situational awareness and adaptability to varying runway lengths and infrastructure. Collaboration with local ground crews, air traffic controllers, and flight planning teams is essential for maintaining efficiency and safety in this dynamic environment.

What is the difference between Seasonal Caribbean Pilot vs Charter Pilot?

AspectSeasonal Caribbean PilotCharter Pilot
CertificationsCommercial Pilot License (CPL), Second-Class MedicalCommercial Pilot License (CPL), Second-Class Medical
Work EnvironmentSeasonal operations in Caribbean islands, often on small aircraftOn-demand flights, private or group charters, often in various locations
Employer & IndustryTourism companies, private operators in CaribbeanCharter companies, private clients, tourism industry

The Seasonal Caribbean Pilot and Charter Pilot roles share similar certifications and work environments, both operating small aircraft within the tourism and private flight sectors. The main difference lies in the seasonal nature of the Caribbean Pilot's work, focusing on specific peak seasons, whereas Charter Pilots often operate year-round on various routes and clients.

More about Seasonal Caribbean Pilot jobs

What cities are hiring for Seasonal Caribbean Pilot jobs?

Cities with the most Seasonal 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 Seasonal Caribbean Pilot jobs?

States with the most job openings for Seasonal Caribbean Pilot jobs include:

What job categories do people searching Seasonal Caribbean Pilot jobs look for?

The top searched job categories for Seasonal Caribbean Pilot jobs are:

Seasonal Caribbean Pilot jobs near you
Infographic showing various Seasonal Caribbean Pilot job openings in the United States as of August 2026, with employment types broken down into 67% Part Time, and 33% Temporary. Highlights an 100% In-person job distribution, with an average salary of $130,916 per year, or $62.9 per hour.

Nantucket Concierge

Tradewind Aviation

Nantucket, MA • On-site

$17.50 - $22.75/hr

Temporary

Medical, Retirement, PTO

Re-posted 16 days ago

Job description

Job Type
Temporary
Description
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) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on 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
About the Candidate / Role
Tradewind Aviation is looking for a seasonal part-time Concierge to be based in Nantucket. The purpose of the Concierge is to create an exceptional experience for every client. As a Tradewind Concierge, you will streamline the process of passengers' arrival and boarding and departure to ensure smooth and timely communication with passengers, aircrew, and the company. The ideal candidate will be Customer Service Driven and enjoy working in a fast-paced, deadline driven environment with rapidly changing priorities. Must be flexible with work schedule and able to work weekends and holidays.
Essential Functions
  • Greets passengers upon their arrival at the terminal and utilizes software for check in process.
  • Collects, organizes, and weighs baggage for pilots.
  • Ensures passenger comfort and keeps passengers informed of any flight delays.
  • Assists with pilot introduction, boarding calls, and baggage handling.
  • Promote Tradewind's "fly personal" brand.
  • Arrive and be ready to work on-time.
  • Raise issues to supervisor in a timely manner.
  • Adhere to all safe work practices and procedures.
  • Stocking lounge and keeping track of inventory.
  • Other duties as assigned.

Requirements
Required Qualifications
  • Excellent customer service and communication skills.
  • Ability to use a handheld device to enter client and flight information.
  • Clean driving record and valid driver's license.
  • Ability to handle fast-paced environments.
  • Proactive attitude.
  • Strong attention to detail with the knack to remember and recognize names and faces
  • Must have housing on Nantucket.

Physical Requirements
  • Prolonged periods of standing outdoors.
  • Ability to lift 75 pounds.
  • Ability to walk and stand and carry luggage for extended periods of time throughout the workday.

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

Apply