When most people hear the words Sail Martha’s Vineyard for the first time, they think of wealth. Sailing is stereotypically a sport of the affluent and Martha’s Vineyard is known as a resort community.

Sail Martha’s Vineyard director Brock Callen acknowledges this fact. “The word sail means elite, inaccessible, expensive,” he said. “Average people don’t think we need the money.”

But a new series of short films attempts to tell the real story of Sail MV, the Vineyard nonprofit known for offering free sailing lessons to Islanders, both kids and adults. The story includes a year-round curriculum with a maritime studies program at the Martha’s Vineyard regional high school (one of a handful in the nation), an early morning adult rowing club and the varsity sailing team at the high school.

“The story needed to be better told,” Mr. Callen said.

Last January, Mr. Callen hired a group of young filmmakers to retell Sail MV’s work from the perspective of its participants.

“They speak better for what it is we do than we can,” he said.

The four mini films capture the day-to-day life of Sail MV, and explain the program’s commitment to the Island’s maritime tradition and to children of every socioeconomic class. It is one of only a few public access sailing organizations in the country.

The films were created by Windy Films, a production company co-founded five years ago by Harvey Burrell, Will Humphrey and Tripp Clemens. Mr. Burrell grew up in Vineyard Haven.

Windy Films primarily creates films for the nonprofit sector, maintaining a focus on social responsibility and research. A Martha’s Vineyard regional high school graduate, Mr. Burrell is currently a senior at Vanderbilt University in Nashville, Tenn. Many of his films have a nautical bent, he said, because he and one of his business partners grew up near the sea. In fact, Mr. Burrell was raised in the house adjacent to the Sail MV headquarters on Main street in Vineyard Haven.

Over the course of four months, the filmmakers visited the Island four times to familiarize themselves with the community and setting of Sail MV. During the first two visits, they didn’t even bring any equipment.

The choice to film in the off-season was deliberate. “I grew up on the Vineyard so I didn’t want to skip out of the bleak reality of winter,” Mr. Burrell said. “So much of the material you see about the Vineyard is the summer stuff and it kind of skips some of the real weight of the issue.”

Ultimately, the crew came away with 80 to 100 hours of footage, which they had to cut back to four films lasting less than three minutes each. In most cases, they spent more than one hour with their interview subjects to tell the complete, authentic story.

“In our experience, things come across a lot more honest and a lot more sincere when people are speaking candidly,” Mr. Burrell said.

The four mini films include one overview of the programs offered and three subsequent films about the adult programs, the high school marine studies program and the passionate children and teens of Sail MV.

“I was definitely nervous about it,” Mr. Burrell said. “I knew at the end of the day, when the work was done, it would be seen by Islanders.”

To shoot the film, Mr. Burrell and his partners used a lightweight digital single-lens reflex camera. The film series had two goals: introduce folks to Sail MV and help raise funds to support the organization.

“The Island needs programs like this desperately,” Mr. Burrell said. “My hope is that some big donor or fundraiser comes out of this effort.”

Sail MV’s annual budget is $550,000, and the organization employs three people full time. “We have to be able to raise $10,000 a week to be able to continue to provide for the children,” Mr. Callen said. “Fundraising is a huge part of what we do.”

Mr. Callen said the organization, which was founded in 1992, tries to create a safe space where kids are exposed to good role models.

“It’s my judgment-free zone,” says high-schooler Margaret Joba-Woodruff in her interview with Windy Films. “And that’s huge for me.”

The films can be viewed at sailmv.com.