Back in the paddle again

We had a terrible kayaking experience during an excursion from a cruise ship in the Caribbean. My son and I did fine, but my wife and daughter wound up tangled under the mangroves, and it wasn’t a pleasant experience for them — even before spiders started falling from the branches.

Fast-forward to last fall, and I convinced my wife to get back on the horse — err, kayak. We were on a trip to Florida, and a large contingent of family and friends were headed over to the Weeki Wachee River for a morning of kayaking.

It was a great experience, in part because we were following the current of the river, so paddling was optional at times — and the scenery, including a passing manatee, was spectacular. Most important, it was there that our son helped my wife figure out the No. 1 rule of kayaking. If you’re trying to get away from something — paddle on that side of the kayak.

We had a great time, and, ever since, we couldn’t wait to get back on the water.

So when an email hit my inbox that Island Spirit Kayak was holding a Demo Day along with Kayaks M.V., where you could test the waters, I immediately forwarded it to my wife.

“You in?” I wrote.

“Yes,” she replied nearly instantly.

That Saturday, we headed to Little Bridge in Oak Bluffs for Demo Day.

Liam Cosgrove, an Islander who’s been working at Island Spirit for seven years, fitted us with life jackets, gave us a quick tutorial in paddling (having those paddles facing the right direction is key), and pointed us in the right direction so that our early paddling would be more difficult than the ride back to shore.

It was a choppy day at Sengekontacket. A stiff breeze provided a great upper-body workout, and the occasional splashing waves helped cool us off from temperatures that — finally — reached the low 70s.

We watched a golfer chase some Canada geese away from his ball at Farm Neck, and terns dive into the water in search of their next meal. A calmer day would have been welcomed, but if we could paddle through the chop on a breezy day, surely a calm day would be a piece of cake.

Once we got to the other side of Sengie, we paddled far enough so that our trip back across the pond would keep us clear of Little Bridge and any possibility of being sucked out into Vineyard Sound. We barely had to paddle to make our way back across in record time, the wind pushing us at a rapid clip.

We returned to the shore smiling, a little tired, but happy with our experience on the water.

There we were greeted by Chick Stapleton, owner of Island Spirit, with a wide smile and a high-five.

Stapleton started this business 20 years ago, after graduating from Boston University and while she was still working as a bartender at Lola’s in Oak Bluffs. (She’s no longer a bartender, and Lola’s changed hands at the end of last season.) She started with one kayak, then another, then more. Pretty soon she was spending her mornings, days, and evenings renting kayaks and paddleboards — and offering a great experience for Vineyard visitors. She now employs 17 people, and provides an on-the-water experience for thousands of people each season. She even offers paddleboard yoga.

Her favorite times are those clear summer evenings, after the sun has set and the wake behind the kayak sparkles with bioluminescence. “This has always been my passion,” she said of kayaking.

Nearby, a handcrafted wooden kayak sparkles in the afternoon sun. “When you’re on the water, you don’t know whether to look at the water or the boat,” Stapleton said. “This is sheer joy.”

At $17,000, it was a little out of our price range.

This year Island Spirit has something new to offer — a three-seat kayak that allows families to go out on the water together. “They’re the new canoe,” Stapleton said, noting that the “sit-atops,” as they’re called, are better than canoes, which can be difficult to maneuver and are much harder to deal with should they capsize or take on water. “Canoes are like 8-track players. They’re out of style.”

During Demo Day, a trio of young boys tested out one of the triples, but the stiff wind pushed them into some reeds, and they struggled a bit. (Although there was so much laughter in the boat, you would have never known they were in any difficulty.)

Cosgrove grabbed a life vest, waded into the shallow water, calmed the boys down, and then climbed into the kayak to paddle them to safety.

“That happens once a day,” he said with a smile. “I love it here … There’s nothing better than getting paid to do what I love to do.”

Riley Sylvia, who is only in his second year at Island Spirit, is just as enthusiastic as Stapleton and Cosgrove. “I like it, it’s a good place to work,” Sylvia said. “You hang out in the sun, on the water, you’ve gotta love that — and you meet tons of people.”

Kayak rentals range from $35 for one to three hours to $150 per week. (It’s obviously a little more for a double.) Paddleboard rentals are slightly cheaper. A variety of tours are also offered.

Stapleton has lost track of how many kayaks her rental business owns. “Hopefully, fewer after today,” she said with a laugh.

Well, I can confirm she now owns one fewer than she did that morning. After a great day on the water and with a lot of summer ahead, we pulled the trigger on a used two-person kayak.

We’ll see you on the water.


You can learn more about Island Spirit Kayak at

This article by George Brennan originally appeared on