Portland Schooner Co - Heart's Desire (Built in 1924)

Sail on historic schooners in Casco Bay!

Posted: Apr 21, 2026

Deckhand

Portland Schooner Co.

Portland, Maine

Wages/Pay
$17.00 - $18.00 / hour + tips
Experience Level
No experience required
Job Start Date
May 04, 2026

Portland Schooner Co., based in Portland, ME, invites applications for late summer/fall, full-time, seasonal Deckhands to serve aboard its fleet of historic, Maine-built wooden vessels: BAGHEERA, WENDAMEEN, TIMBERWIND, HEART’S DESIRE, VELA and M/V RUTH. Come sail in beautiful Casco Bay and live in one of the best places in the U.S. according to U.S. News & World Report.

Portland Schooner Co. conducts a variety of public shipboard programs from May through October, including two-hour public sails, private charters, overnights, as well as educational and sail training sessions.

We offer a fast paced, hardworking, and fun environment with daily shifts ranging from 3-5 days. This is a unique opportunity to learn traditional sailing or further your growth as a sailor aboard one of our tall ships. In addition to responsibilities associated with sailing, candidates must be willing to provide an exceptional experience to our valued guests while vigilantly providing a safe environment at all times. Enthusiasm for working with the public on a daily basis is essential. We need positive individuals who can help deliver a superior experience for our guests. This means having a great attitude, good work ethic and friendly personality.

A successful candidate will have a strong passion for sailing as well as historic schooners and a desire to share that passion with others. All applicants are welcome although preference will be given to candidates with previous traditional sailing experience. MUST BE ABLE TO PASS DRUG TEST per USCG requirements.

We offer strong, industry-leading compensation that is commensurate with experience. Preference will be given to candidates interested in returning each season.

How to Apply

Please send a resume to jobs@portlandschooner.com

Apply Now

Contact Info

Portland Schooner Co.

At Portland Schooner Co. we love the sea and our Maine-crafted, wooden schooners that still sail it proudly. And, we love the opportunity to share this passion with our guests sailing four times a day, seven days a week from the Old Port in Portland, ME.

Location
Maine
Season
Summer and Fall
Staff size
15+ in season
Housing
Whether included in the compensation package or provided at a cost, housing is provided for staff.
Housing details
We have shared apartments available for employees for the duration of their time with the company. The affordable rent will be handled through payroll.
Family housing available
Yes
Pet friendly
No
Meals
None
Cell phone service
Yes, most carriers
Internet access
Good
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