This was a 4 hour charter which allowed enough time to sail the bay, explore the coast of Oak Bluffs, motor around the harbor of Oak Bluffs, sail back to Vineyard Haven and have a short swimming session.
It was a beautiful afternoon having three generations of a family relaxing and sailing. The youngest is starting sailing camp next week, and Grandma had a thoughtful idea: she wanted to give him the experience of being on a larger sailboat before he started navigating smaller ones at camp. Her goal was to inspire confidence—and maybe spark a lifelong love of sailing. It was a special moment for me, too, as I remembered being that same age, just starting to learn the ropes of sailing myself.
We sailed around Vineyard Haven Harbor and enjoyed the sights along East Chop on the way to Oak Bluffs. Once we reached Oak Bluffs, we entered the harbor and did a loop around to see the town from the water. I know from my own experience growing up enjoying Oak Bluffs, that it is a whole new perspective to see a town you love from a boat, on the same water you’ve always admired from shore.
I pointed out Nancy’s Restaurant, Our Market, the Summer Camp Hotel, and all the private docks on the east side of the harbor—places hidden from view unless you’re on the water.
Back out in Vineyard Sound, we made two passes by Inkwell Beach, where Grandma is a proud and active member of Polar Bears—a dedicated group of early-morning swimmers who meet to fellowship daily. It was clear that this beach holds a special place in her heart, and it was lovely to see it from the water.
We continued back towards Vineyard Haven, making a close and well-timed pass with the ferry Martha’s Vineyard. Father and son relaxed on the bow, while Mom and Grandma enjoyed the breeze from the cockpit.
When we returned to Vineyard Haven, we tied up to a mooring, and father and son took turns jumping into the water and swimming. Although he was a little apprehensive at first, the boy became very enthusiastic about the swimming and enjoyed the ease of getting on the boat via the swim platform—then jumping right back off again. Mom and Grandma were thrilled to see him conquer his fear and start to enjoy this new chapter in outdoor adventuring.
We wish him the best of luck with sailing camp, and we hope to have him back on board Our Passion again soon—to show off his newfound skills.
