I’m not showing off… This is what a great charter is like. This is just how we roll.

This was a five hour charter which was enough time to do a lot of sailing. We originally envisioned swimming and grilling as part of the itinerary but the sailing was going so well that the guests wanted to keep the boat moving.

family on bow of sailboat enjoying the sunset

I thought we had a good charter yesterday when I went to bed.
But as I woke up this morning and thought more deeply, I realized we had an amazing charter yesterday.

Although our goal is to help our guests make memories they’ll never forget, I realized this morning that yesterday’s charter was one I will never forget.
“Family is what you make it,” and watching a blended family begin to form right before our eyes was a beautiful and unexpected moment.


It was a perfect example of why we do this — and a reminder that we’ve truly found our path in life.We started the day early, climbing around and fixing a furling line on the mizzen mast while tweaking the rigging and systems in pursuit of the nautical perfection we know is unreachable  but still worth chasing.
After that, we prepared for our guests’ arrival picking them up at 4 PM on the dock.

The winds were light, and we motored away from the dock into the center of the inner harbor. When asked whether they’d like to swim first or sail, the lead charterer — the father, an experienced sailor — optimistically asked us to set the sails, hoping to spend as much of the afternoon under sail.

We raised the main, then the mizzen, turned downwind pointing out of the harbor, and unfurled the genoa. We were only making about 2 knots, creeping along East Chop while admiring the houses and flying the drone they brought with them.

As we passed East Chop, the wind picked up to a steady 10–15 knots, and we headed up toward Edgartown.
After a successful drone flight, the father gladly took the helm, while the rest of his family gathered around the cockpit table for chips, guac, and salsa. Then Mom took the helm and enjoyed it. Afterward Mom and Dad went up to the bow to hang out, and his son took the helm and did great.It was around then that we realized something special: this was a newly blended family. This was their first vacation together. It was only the second time the father’s son and the mother’s daughter had met.
They were all having such a good time and bonding so well that I didn’t even notice what was happening: a new family unit was forming right in front of us on Our Passion.
The glue was our boat and the sailing experience we were providing.


One by one, they all ended up on the bow together, lounging around, talking, and making memories.

We turned around at 6:00 PM  and headed back to Vineyard Haven with all four guests still on the bow. One by one, they started to come back for sweatshirts as the temperature dipped, but they returned to the bow to hold onto the great moment they were having together.

As we approached East Chop at 7:15 PM, we still had wind, but the current slowed us down to a crawl even with all three sails still up. At this point, everyone had returned to the shelter of the cockpit, and we watched a bank of fog drift over the treetops of Vineyard Haven and down the banks onto the waterfront.
The family agreed that it was best to keep sailing and revise our earlier plan to have a cookout and swim off of the stern.

The amazing sunset I had been hoping for didn’t materialize, but we tacked through the anchorage, then the mooring field, and then into the inner harbor as dusk gave way to full darkness.

The father asked me at one point if I was showing off, which I assumed was because we were sailing through such tight quarters. I said no, that this is just good practice for when we might need to maneuver without an engine, instead of just choosing to.

We slowly drifted by the Alabama and then the Shenandoah as we sailed almost to the high-end docks of Vineyard Haven.

Looking back, maybe we were showing off a little but it was quiet, subtle maneuvering at less than two knots which reflected the calm confidence Capt. Lynne and I have built through years of sailing together.
It felt normal and natural, like, “this is just how we roll.”

We made one last tack across the docked bow of the new freight ferry, the Aquinnah, and headed straight through the thoroughfare of the inner mooring field towards Owen Park.
We had just enough air in our sails to quietly creep up to the Owen Park Dock, and with a few taps of the bow thruster, we were tied up.

That’s when it hit me, we had not motored at all in the last four-plus hours, even though the urge had hit me more than once to be ready to power up the engine.

The family was very appreciative of the trip and the time they spent aboard Our Passion.
One detail that made me proud was the fact that the father is a commercial airplane pilot who also has sailing experience.


He is entrusted with delivering people safely and in comfort, and his acknowledgment that we had done a good job was especially heartfelt, because he knew how special the day had been.We all said goodbye in the dark, but we could still see everyone’s smiles.
We hope to have them back soon and can’t wait to refresh, reload, and set our sights once more on creating lifelong memories for the next guests aboard Our Passion.

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