At the State of the Island Tourism Breakfast, leaders of the Vineyard’s tourism industry reviewed visitor trends from the past year and discussed the future of the Island’s businesses as they navigate the rise of artificial intelligence.
Panelists spoke on topics ranging from what makes a destination iconic to how businesses can begin using AI as a member of their team.
The executive director and deputy director of the Martha’s Vineyard Chamber of Commerce, Erica Ashton and Alessandra Hagerty, kicked off the day with a review of the 2026 tourism season.
According to Ms. Ashton, out of 10 visitors, 9.28 were likely to return, which the chamber noted as a high return rate.
“That generational visitor, the people returning year after year, is a huge market for the Island,” Ms. Hagerty said.
Across the five airlines that serve the Vineyard, there were nearly 70,000 passengers recorded for the year to date. This number is down 3.4 per cent from 2025, which was a record year for air travel.
However, Ms. Ashton reported that there were 30,627 passengers in August, which is up 5.1 per cent from last year. The chamber determined that August was a particularly strong month for tourism, continuing a long-held trend.
“It’s no surprise that August was our busiest month,” Ms. Ashton said.
In terms of where visitors are coming from, Boston remains the top origin point, followed by Providence, New York, Hartford and Albany.
Elizabeth Sutherland, president and CEO of Sutherland Weston Marketing Communications, spoke about marketing Vineyard businesses specifically to target AI search engines.
She advised businesses to find what makes them unique, and explained how AI tools look for specificity. She said businesses can use that to their advantage.
“For years, a huge part of digital marketing was about visibility,” Ms. Sutherland said. “But when someone asks an AI tool for a recommendation, visibility is now only part of the job. There’s now a second test, and that is: are you a good fit for what they asked?”
Ms. Sutherland dissuaded businesses from using broad marketing terms like “unique,” “unforgettable” or “charming.”
“There is a tendency in marketing to want to be for everyone, because we’re afraid that specificity will cost us customers,” she said. “But when people are choosing among many options, it is almost never helpful, and it certainly isn’t helpful for AI tools.”
Other AI experts spoke during the event, such as Dave Everett, founder of White Fang AI, and David Dragas, founder of Vidd AI.
Erin Goldson, founder and CEO of Vineyard Icon, a cultural program that works to preserve Vineyard history, talked about giving back to local nonprofits and honoring Island leaders. This summer the organization honored Eric Holder, United States attorney general from 2009 to 2015, with the Vineyard Icon award.
During her presentation, Ms. Goldson explored what makes the Vineyard an iconic tourism destination. She identified the Island’s history and legacy as defining characteristics, alongside its strong sense of community and safety.
“My family has come for five generations,” she said. “AI can recommend a beach. But AI can’t build tradition. AI can’t replicate my parents getting married here, and my sister wearing the same dress years later. AI can’t replicate that feeling when you first walk off the ferry.”