Drive a truck in a small island community on Monhegan Island off the coast of Maine

Expired: Mar 19, 2026

Expired

This job post has expired.

Shining Sails is a small family-run Inn, Bed and Breakfast, and Property Management business located on Monhegan Island. Monhegan is a quiet and remote tourist destination reached by an hour-long ferry ride. Breakfast is provided each day and housing in a single room with shared kitchen and bathroom is provided to employees. Any employees occupying housing must agree to the housing agreement. All positions at Shining Sails require a smartphone to access work-related apps. Schedules rotate with at least one day off per week.

The Shining Sails Luggage Porter (aka Truck Driver) is principally responsible for utilizing company vehicles to move guest luggage from the ferry wharf to their units, collecting and sorting trash and recycling from all properties and delivering it to the island transfer station, groundskeeping, mucking the chicken coop, and light maintenance. The ideal candidate will have good time management and organizational skills and will be able to self-direct and adjust to changing guest and team needs throughout their shift. Must be able to regularly move up to 50 lbs throughout a six-hour shift. Must have experience with vehicle operation and must be able to regularly and safely operate a vehicle on shared, narrow, and roughly surfaced roads with heavy pedestrian traffic. Will be responsible for inspecting and maintaining vehicle fluid levels, including fuel and general vehicle safety. An ideal candidate will have experience with and must be able to safely operate a push lawnmower, weed eater, and basic power tools or equipment. Must be able to read, write, and speak English. Must be able to regularly and clearly communicate with guests in a welcoming and courteous manner. Must be available to work until mid-October. A typical workweek is 38-40 hours with a minimum of 6 hours per day. Salary requires a minimum of 38 hours; tips are estimated at an average $200/week.

How to Apply

Email a .pdf resume to info@shiningsails.com. Please specify in the email which position you are applying for.

Contact Info

Shining Sails Bed & Breakfast

Shining Sails is a family-run B&B, Inn, and Property Management business. We are a close-knit staff operating 11 units for nightly rental and 20 privately owned homes for weekly rental.

About CoolWorks

Since 1995, CoolWorks has connected adventure-seekers with job opportunities in amazing places—from national parks to ski resorts, summer camps to dude ranches. We help people trade screen time for real time—meaningful experiences that spark connection and growth. Your next great adventure is waiting. More About CoolWorks

Need Help?

Check out our Help Center for FAQ's and helpful articles on how to use CoolWorks. For more in-depth information on how to navigate the world of Jobs in Great Places®, whether you're a Job Seeker or an Employer, visit our Resources page.
Scroll Less. Live More.