Sailing On Boston Harbor

Sailing On Boston Harbor

04 Jul 2025
Massachusetts, Boston, 02108 Boston USA

Sailing On Boston Harbor

Classic Harbor Line (Classic), a boutique, tour boat operator is seeking a seasonal Deckhand to join our growing business. Classic offers a unique work experience cruising Boston harbor and entertaining public guests. Our ship, Adirondack, is a versatile space for weddings, corporate entertainment, birthdays, and sightseeing. This is not a live aboard position. Looking for someone with some sailing experience for part or full time hours through October.

Increased pay is offered to those candidates that have:

A self-starter attitude

Take initiative

Problem-solve on their feet to fix an issue

Have open availability

Find weak areas and work to strengthen them

Exude a hard-working attitude

Demonstrate an ability to lead a group

Have open availability

Earn sea-time towards your captains license for 100-ton Inland Masters

401K benefits are offered after 750-hours

Gratuity and tips are accepted on public trips along with competitive hourly pay.

Health Insurance benefits

Bonus pay

Adirondack III offers public and private sails.

Public sails: We offer Day sails and Sunset sails every day of the week in peak season. We sail 2-5 times a day (more on the weekends) Our sails are 90-minutes – 3 hours long.

Private sails: Adirondack III hosts many private events throughout the summer. Clients will book Adirondack III with a catering and bar package. Our deckhands are also our servers.

Our deckhands will be responsible for:

Prepping the ship for departure

Stocking bathrooms, beverages, utensils, etc

Informing Management of low stock items or broke

Cleaning between trips and deep cleaning on scheduled days

Setup for special events

Be charismatic and friendly with guests

Improving the overall aesthetics of the vessel

Increased pay is offered to those candidates that have:

A self-starter attitude

Take initiative

Problem-solve on their feet to fix an issue

Have open availability

Find weak areas and work to strengthen them

Exude a hard-working attitude

Demonstrate an ability to lead a group

The ideal candidate will need to have:

some sailing experience (preference)

Have some experience bartending

Must have their own housing in Boston or surrounding area (we are not a live aboard ship)

.

Pay Starts at $17 + DOE Plus Tips averages about $30/hour

401K benefits are offered after 750-hours

Gratuity and tips are accepted on public trips along with competitive hourly pay.

Health Insurance benefits

Bonus pay

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