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From May through October, apprentices and instructors get out on the water in our fleet of traditional and modern vessels. Formal and informal training occurs throughout the season as first-sear students learn sailing basics while the second-years refine their skills. The sailing season includes at least one overnight expedition along with other opportunities to get out on the water. Local racing clubs are always looking for willing crew, and there are occasional offshore sailing opportunities delivering sea education vessels along the northeast coast.

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The greatest builders are also confident mariners, and the greatest sailors can fix their craft at sea. Having the opportunity not only to build but also to sail traditional boats is one of the many components that sets The Apprenticeshop apart from other schools.

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During winter months, Friday afternoons are focused on apprentice-led presentations covering a wide variety of topics, including knot tying, sail theory, navigation, and boat handling. Additionally, students tour mid-coast boat yards, visit sail makers, maritime museums, and even model ship makers and traditional tool enthusiasts. Local boat builders and crafts people give demonstrations at the Shop on a variety of topics such as hand saw sharpening and log hewing. Apprentices may also have the opportunity for offsite training in skills such as wood turning and blacksmithing.