Riding the Winds of Change

Vineyard businesses tend to come and go. The vagaries of the seasonal economy, high rents, a shortage of staff housing, the changing nature of the Island – they all make longevity difficult to achieve here. But if you rented a Sunfish on the Lagoon in Vineyard Haven in 1962, you rented from the same family business that’s there today.

Wind’s Up! is celebrating its fiftieth anniversary. Founded in 1962 by John Cassel and his brother-in-law Ned Finegan, Selfin Sunfish Rental put aspiring sailors on the water by the hour, day, and week.

After a few years, John bought out Ned, then in 1974 he sold the business to his brother, Doug Cassel, and Doug’s wife, Pam. They expanded the offerings to include sailing instruction. They added windsurfing to the curriculum in 1980, and in 1985 opened a retail store/surf shop under the name Wind’s Up! A few years later the boat rental/school adopted the Wind’s Up! moniker, then added kayaks to the rental fleet in 1991, and stand-up paddle boards (SUPs) in 2009. Staying true to its roots, Wind’s Up! still offers Sunfish rentals as well as rentals and instruction on sloops, catamarans, and windsurfers. Pam Cassel and her son Geoff now run the business.

Asked what has kept them in business for half a century, Pam says, “You love what you’re doing because it helps other people love what they’re doing....We provide ways to be outside and enjoy the sun, wind, and water, which is what people come to the Vineyard to enjoy.” On an island where access to the water can be hard to come by, the variety of vessels at Wind’s Up! provides an easy entry. “You can get out on the water without a lot of expertise, and then learn and get more adventurous.”

The Cassels bring a lifetime love of wind and water to Wind’s Up! Pam learned to sail in the late 1940s at the Sailing Camp in Oak Bluffs and became an instructor there. She met her husband, Doug, a long-time member and fleet captain (and later, commodore) of the Vineyard Haven Yacht Club, in 1953. Geoff was a precocious sailor. As Pam tells it, when Geoff was four or five years old, they were playing with a toy sailboat on the Lagoon one day when the string broke and it sailed away. “I told him we can get it in a Sunfish and went inside to get the life jackets. When I returned, he was sailing out to get it himself. He sailed out and picked it up and returned perfectly. We hadn’t taught him a thing.”

Geoff parlayed his early enthusiasm not just into Wind’s Up!, but into a competitive sailing career, including a try, ultimately unsuccessful, at making the Olympic team in the 1980s. He’s now an avid windsurfer and paddler, particularly enjoying stand-up paddle boards. (He also kitesurfs, but Wind’s Up! doesn’t rent kitesurfing gear, as it can be dangerous and requires more open area than the Lagoon location provides.) Geoff lives in Maui in the off-season, as befits a water-sports enthusiast.

Many members of the Cassel extended family have worked at, or still work at, Wind’s Up!, including all of Pam and Doug’s children, and many of their grandchildren. From 1977 to 1994 (a mere seventeen years), the family even ran the Portside restaurant where the retail store is now. “Some members of the family liked it,” notes Geoff, “but hamburgers really aren’t our passion.”

The Cassels aren’t just passionate about the sports aspect of the business. “People come for twenty years straight and rent a Sunfish...and then come back with their kids and grandkids,” says Geoff. “And kids return to work year after year, and when they leave, they come back and say, ‘This was the best job I ever had.’...We like to keep it a family-friendly, and just friendly, atmosphere.”

Pam sums it up neatly: “It’s sort of like an extended family.”

Secrets behind a long run

Q: Aside from loving what you do, what has accounted for the longevity of Wind’s Up!?

A: Geoff Cassel: The popularity of the activities we do, and the diversity of what we offer – lessons, rentals, retail – help us deal with the seasonality of the business, which is probably the biggest challenge. But you have to diversify to stay steady. We started with Sunfish. Windsurfing was the fastest-growing sport in the world in the eighties and early nineties. Paddle sports’ popularity has grown in the last several years and Wind’s Up! has evolved to meet this demand. But that won’t necessarily always be the case. It was an evolution; you never know what direction your business is going in.