Catching the Island Spirit in a Quiet Cove

Paddleboarding in Oak Bluffs MA with Island Spirit Kayak.
Mary paddleboarding in Oak Bluffs MA with Island Spirit Kayak.

Chick Stapleton was born on the island, and thirteen years ago she started her business renting kayaks and guiding, when she was just 21. Today, Island Spirit Kayak boasts a fleet of 50 boats that can accommodate 64 paddlers, and she also rents out paddleboards. She’s successful enough to spend three months a year with her young family ┬áin Vieques, another island located off Puerto Rico.

I asked her if she’s brought her business south. “There are ten outfitters who rent kayaks there, and it’s pretty tough to compete with the locals,” she said. So she takes care of her 18-month old son and relaxes until it’s time to return to her homeland in the spring. She runs a shaved ice stand that gives her a foothold on the prime real estate by the bridge where she keeps her kayaks during the day.

We joined Tex, a young Oregonian, our guide on a paddle into the cove next to Oak Bluff’s little bridge, and got a close look at a pair of oystercatchers, their long orange beaks attacking their prey as tiny babies looked on. Up on a hill was a gigantic white house, it’s owned by director Spike Lee. After relaxing with the birds we followed the channel below the bridge and out into the glassy ocean.

Chick Stapleton, of Island Spirit Kayaks

After some ocean paddling we retreated into another cove, in this one a catboat with no mast has been moored to a pier you can see from the road for at least four decades. It’s got a distinctive eyeball on its bow. Down inside the cove, a nest of osprey’s have lived for years. We learned that this pair is so dominant that three other poles put up were never used since the other birds so feared the ones who live there already.

We wanted to give paddleboarding a try, so we grabbed two of the very lightweight 3-feet wide boards and waded out, being careful not to let the delicate fin hit the bottom. The trick here is to get up on the boards on your knees and begin paddling then slowly get up.

It’s not as tippy as you might think, and after a while using the long paddle is easier, it’s quite counter-intuitive to be paddling standing up! I’ve seen these being ridden down big waves in Maui, I think to do that we’d have to have a lot more practice!

Martha’s Vineyard kayaking