When it comes to tall ships, there are few things Capt. Robert S. Douglas — the legendary, 88-year old wooden boat builder, designer and captain of the famed schooner Shenandoah — hasn’t achieved in his lifetime.

A lifetime achievement award was one them.

That changed last Thursday night, when Mr. Douglas was honored by Tall Ships America, the largest tall ship education programmer in the world, for his “lifetime of achievement under sail.”

Bestowed annually, the prestigious award is given to an individual who has dedicated their life to getting people to sea, and worked to preserve the traditions and skills of sail training.

Thursday’s ceremony, normally held in person, took place over Zoom and included rousing introductions by Vineyard boatbuilder and sailor Gary Maynard, as well as international tall ship captain Daniel Moreland.

“From small craft to large, [Mr. Douglas] has nudged and helped so many — the world of sail training is a vastly richer place for having Bob Douglas in it,” Captain Moreland said during the event.

Mr. Douglas’s long journey as a sea captain actually began in the air. Achieving the rank of captain as a jet fighter pilot in the Air Force from 1956 to 1958, he returned to Martha’s Vineyard after he was able to walk away alive from his downed F-86 Saberjet. From then on, he set his sights on the water, Mr. Moreland said in his tribute to the captain.

“[Mr. Douglas] had in mind a life under sail, sharing the majesty of sailing ships and historic New England along the coasts near his home on Martha’s Vineyard,” Mr. Moreland said during the ceremony. “He succeeded beyond his imagination.”

In 1964, Captain Douglas designed and built the 108-foot top-sail Shenandoah schooner, the largest — and only — square-rigged tall ship of its size in the world.

The swashbuckling air and sea captain has skippered Shenandoah ever since she first sailed into Vineyard Haven harbor, initially using the boat as a recreational cruiser and later transforming it into a vessel for marine education programs. Week-long trips on the boat soon became a rite of passage for almost all Island fifth-graders.

In his tribute to Mr. Douglas, Captain Moreland described how “literally generations of young people have gotten their first taste of the salt sea” on the Shenandoah, ranging from future masters, to mates to model makers. He also noted that Mr. Douglas helped preserve the rich maritime heritage of Vineyard Haven, turning it into a mecca for classic wooden sailing vessels.

“The island itself is all the better for the power of example of one man,” Captain Moreland said.

Along with the Shenandoah, Mr. Douglas also purchased and rebuilt the early 20th-century schooner Alabama in 1967, with both boats and their Black Dog flags quickly becoming a welcome site for anyone sailing into the Vineyard Haven harbor.

Captain Moreland, who has circumnavigated the globe seven times and has a license to sail anywhere in the world, got his start from Mr. Douglas, too, who helped him set up his three-masted barque Picton Castle. On Thursday, he took the opportunity to thank Mr. Douglas, his wife Charlene, and his four sons, Robbie, Jamie, Morgan and Brooke.

“Captain Douglas, thank you for your service. Thank you for your devotion making this a lifetime of achievement. Thank you for sharing your passion so readily and broadly,” he said.

Last year, Mr. Douglas donated the Shenandoah to FUEL, an Island nonprofit dedicated to continuing marine education programs on the vessel. The organization is currently fundraising and hopes to restart programming on the boat in June of this summer.

On Monday, Ian Ridgeway, who heads the nonprofit with his partner Casey Blum, said he and Mr. Douglas were driving down to Mystic, Conn. to check on the Shenandoah, which was undergoing extensive repairs on its stern. He said all six Island schools are scheduled to take trips on the boat come summer.

In his remarks, Captain Moreland concluded by saying he was excited to see the Shenandoah sail on — a next chapter just as exciting as its first.

“Thanks for giving your precious Shenandoah to Ian and Casey, to carry on your good works,” he said.