Only Nat Benjamin could sail more than 1,700 miles to Haiti in a wooden boat he designed and built, deliver enough donations to keep an orphanage going, hand out a hold full of critically needed supplies, change dozens of lives for the better, and call it easy.

“It’s really easy to make a big difference there,” he said, speaking before a packed house at the Black Dog Tavern Wednesday evening for the Sail Martha’s Vineyard lecture series.

Full crowd at the Black Dog Tavern. — Steve Myrick

Mr. Benjamin talked about his 2014 voyage to Haiti, by way of Bermuda, and then to Cuba, by way of Jamaica. He regaled the audience with tales of sailing, exotic customs and primitive boat building, showing dozens of photographs to illustrate the talk.

“We took off on a beautiful day,” he said, referring to his schooner Charlotte sailing out of Vineyard Haven Harbor the day after Thanksgiving, in the middle of a snow storm. He and his crew later arrived at Ile a Vache, a small island off the south coast of Haiti.

“It’s about as far from Haiti as we are from the Cape,” he said. Like everybody else, he took the local mode of transportation to the main island, a rickety long boat.

“That’s the Steamship Authority,” he said to hearty laughter. “You won’t find a life jacket. I don’t think anyone could swim. You’ll find a sputtering outboard. But we made it.”

The respected naval architect and boat builder was clearly in awe of Haitian craftsmen, building fishing boats that are a matter of survival for their families, with the most basic tools. He showed pictures of several boats under construction.

“They build everything right on the beach, with only machetes and axes,” he said.

Mr. Benjamin carried everything he could fit in his classic schooner, and told many stories about handing someone a vegetable grater or a worn out sail that was a life-changing gift for people still very much struggling from the effects of a devastating earthquake in 2010.

He visited one of the many orphanages in Haiti, where a nun had run out of money to pay her helpers and buy food. Mr. Benjamin, along with his wife Pam, who flew to the island to join the crew of Charlotte, delivered about $8,000 in cash. The money was raised through Ms. Benjamin’s non-profit organization Sense of Wonder Creations, in small donations from friends and family on Martha’s Vineyard.

"It's really easy to make a big difference," Mr. Benjamin said of his trip to Haiti. — Steve Myrick

From Haiti, he sailed to Jamaica to resupply, then on to Cuba. He made an effort to cut through an angry sea of bureaucracy for the proper documents to enter into Cuba, before he left. That didn’t work out too well, but he found a simple solution. He just ignored the bureaucracy, and sailed into the port city of Cienguegos with flags flying. It was the same day President Barack Obama announced a lifting of the 50-year embargo on Cuba.

Mr. Benjamin said his vessel was met by customs agents, who gave him and his crew a warm and polite welcome after checking their cargo and taking their temperature to make sure they were not bringing communicable diseases to Cuba.

He showed pictures of Cuba’s famous fleet of vintage cars, including a Cadillac whose driver said his grandfather bought it new in the 1950s. He also spoke of the city’s breathtaking opera house,

The Sail MV dinner and lecture series will host three more guests this winter at the Black Dog Tavern. The next guest, scheduled for Feb. 10, is Andrew Lipman, a historian who has studied and written about New England maritime history. He will talk about his book Saltwater Frontier, which chronicles the little known story of conflict at sea between Native Americans and the earliest Colonial settlers.