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Weekend Flight Instructor Jobs in Boston, MA (NOW HIRING)

The RPO shall observe a previously certified RPO, an FAA employee, or Contractor instructor performing RPO duties on a minimum of five (5) simulation scenarios. The RPO will receive on the job ...

Ramp Agent

East Boston, MA · On-site

$16.75 - $20.75/hr

Ability to work all shifts including weekends and some holidays * Reliable, dependable, and responsible * The requirements listed below are representative of the documentation required: * Valid ...

New

Ramp Agent

East Boston, MA · On-site

$16.75 - $20.75/hr

This position will often require working nights, weekends and holidays * Must exhibit exceptional knowledge of Cape Air and must embody the Cape Air MOCHA HAGoTDI spirit

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Weekend Flight Instructor information

See Boston, MA salary details

$27.2K

$102.8K

$158.1K

How much do weekend flight instructor jobs pay per year?

As of Jun 11, 2026, the average yearly pay for weekend flight instructor in Boston, MA is $102,789.00, according to ZipRecruiter salary data. Most workers in this role earn between $75,000.00 and $121,700.00 per year, depending on experience, location, and employer.

What is a Weekend Flight Instructor job?

A Weekend Flight Instructor is a certified flight instructor (CFI) who provides flying lessons primarily on weekends. This role is ideal for instructors who have a full-time job elsewhere or prefer a flexible schedule. Responsibilities include teaching flight maneuvers, conducting ground instruction, and ensuring student pilots meet safety and regulatory standards. Weekend Flight Instructors typically work with student pilots pursuing private, commercial, or other pilot certifications.

What does a typical weekend schedule look like for a Weekend Flight Instructor, and how are student lessons structured?

As a Weekend Flight Instructor, your schedule is typically concentrated on Saturdays and Sundays, with lessons planned throughout the day to accommodate students who are balancing flight training with weekday commitments. Most instructors manage multiple students, dividing time between pre-flight briefings, in-flight instruction, and post-flight debriefs. Lessons are usually tailored to each student's progress and may include ground school segments, simulator sessions, and real-world flight time. You will often collaborate with other instructors and administrative staff to coordinate aircraft availability and manage training documentation. This structure allows you to maximize instructional time and provide focused, individualized training within the constraints of a weekend-only role.

What are the key skills and qualifications needed to thrive in the Weekend Flight Instructor position, and why are they important?

To thrive as a Weekend Flight Instructor, you need a certified pilot’s license with instructor credentials, strong aviation knowledge, and a solid record of safe flying. Familiarity with aircraft systems, flight simulators, and digital aviation logbooks or scheduling tools is essential. Excellent communication, patience, and motivational skills help create a positive learning environment for student pilots. These qualifications are crucial for ensuring safety, effective training, and fostering student success during condensed weekend instruction sessions.

What are the most commonly searched types of Flight Instructor jobs in Boston, MA? The most popular types of Flight Instructor jobs in Boston, MA are:
What cities near Boston, MA are hiring for Weekend Flight Instructor jobs? Cities near Boston, MA with the most Weekend Flight Instructor job openings:

Remote Pilot Operator

PenBay Media LLC

Boston, MA • On-site, Remote

Full-time

Posted 27 days ago


Job description

PenBay is looking for motivated, computer-savvy individuals to work as Remote Pilot Operators. No aviation experience is required, but helpful. Experience as a computer operator, RPO, air traffic control specialist, or (student) pilot is highly desirable. Candidates that have completed aviation studies coursework, are certified in the terminal radar lab or en route lab, or otherwise possess a working knowledge of the FAAO JO 7110.65 are preferred.
Position Summary:
The Remote Pilot Operator (RPO) operates a combination of Cathode Ray Tube (CRT)/keyboard/Voice Communication System (VCS) to simulate the actions and communication of pilots and remote ATC facilities during medium and high-fidelity training exercises. RPOs receive voice commands from students, input proper entries into the automated system to simulate pilot actions, translate displayed information into appropriate ATC terminology, and respond to the student via the VCS utilizing proper phraseology.
PLEASE NOTE: This is NOT a UAS / UAV / RPV Pilot / Operator position
This is a Full-time position
Requirements
Qualifications:
High school diploma or equivalent and at least one (1) year of experience in a comparable position.
Demonstrated minimum keyboard speed of forty (40) wpm with ninety (90) percent accuracy rate
Ability to read and interpret materials such as diagrams and manuals
Ability to speak clearly and be understood
Proficiency with MS Office Suite (Word, Excel, etc), desirable
Basic familiarization of current technologic tools (tablets, notebooks, applications, etc.) a plus
Experience working in a multidisciplinary team, preferred
Candidates will be subject to FAA security screening
Competencies and Skills:
RPO must be laboratory certified within the first 120 days calendar days of reporting for duty at the facility.
Exceptional customer service orientation
Ability to work productively with a wide range of people and co-workers
Effective oral and written communication skills
Effective team building skills
Certification Requirements:
Each new RPO shall complete knowledge and skills tests for each area/sector to be supported.
Each knowledge test will be graded and must be passed with a score of at least 70%.
Upon successful completion of the knowledge tests, the RPO will begin training for the skills tests. The RPO shall observe a previously certified RPO, an FAA employee, or Contractor instructor performing RPO duties on a minimum of five (5) simulation scenarios. The RPO will receive on the job training on at least five (5) but no more than twenty (20) simulation scenarios on each control position to be supported, after which an FAA representative will observe their performance and determine if certification will be granted.
The RPO shall achieve simulation laboratory certification within one hundred twenty (120) days of reporting for duty at the facility.