Iconic 152-Foot Engine-Free Schooner Sails Into Martha’s Vineyard One Final Time

Shenandoah, the 152-foot topsail schooner reportedly the only one like it in the world without an engine for propulsion, sailed home to Martha's Vineyard one last time on Friday, September 18, 2026.

Launched on February 15, 1964, in South Bristol, Maine, Shenandoah sailed for 62 seasons out of Vineyard Haven, carrying thousands of schoolchildren on week-long immersive voyages where they learned maritime skills and teamwork.

Over the years, the schooner introduced thousands of others to sailing.

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62 Seasons of Maritime Education on Martha's Vineyard

Martha's Vineyard Magazine reports that in 2020, Shenandoah's designer, builder, and captain, Robert Douglas, founder of the Black Dog Tall Ships, gifted the vessel to the nonprofit Martha's Vineyard Ocean Academy, which continued to use it as a classroom with sails.

U.S. Coast Guard Inspection Forces Retirement

During a spring haul-out at the Fairhaven Shipyard in 2025, a U.S. Coast Guard inspection determined that the necessary repairs for Shenandoah would cost significantly more than replacing the vessel. The academy decided to retire Shenandoah.

Building Shenandoah II: Fundraising and Future Plans

The Vineyard Gazette reported, "The Ocean Academy remains excited about the construction of a new boat, the Shenandoah II."

The paper said the academy has a fundraising goal of $6.2 million to begin construction on the new vessel, which will be equipped with engines that will make future voyages easier and allow the ship to carry students year-round and not just during the summer.

To date, the academy has raised just under $5 million.

Phase Two, including rigging and fitting out the ship's interior, an endowment for scholarships, and expansion of programming, will require the academy to raise an additional $3.6 million.

Unless the academy can lease a vessel, educational programming will be put on hold for a couple of years until the new vessel is completed.

Some hope the Shenandoah can become a permanent tourism fixture on Vineyard Haven's waterfront.