“We made it back safe and with plenty of time to spare! Thank you again for the fabulous day. Your suggestion was well worth it and it was a pleasure to chat with you and Lynne!! Thank you so much!”
-Alexis N.
This was an 8 hour Martha’s Vineyard to Cuttyhunk Island charter that was assisted by a favorable current and tide cycle on this particular day. 10 hours would have allowed for more time exploring and 11.5 hours would have allowed for the full round trip return to Edgartown depending on the tides and currents of the day.
We had the opportunity to take a lovely couple to Cuttyhunk today. They are originally from South Dakota and now live in Brooklyn, NY.
They came aboard Our Passion at 9am in Edgartown for a Martha’s Vineyard to Cuttyhunk charter, and we picked up a favorable current just outside the harbor, helping us motor past Oak Bluffs, Vineyard Haven, and down Vineyard Sound to Canapitsit Channel — a very narrow channel known for its strong currents and challenging navigation.
Crossing the channel took us from Vineyard Sound into Buzzards Bay — specifically outer Cuttyhunk Harbor.
We snaked our way into the very protected inner Cuttyhunk Harbor and dropped our guests and Capt. Lynne off at the town dock.




They took in the sights and then decided to order fresh lobster rolls from some of our favorite people on the South Coast, who run the Cuttyhunk Café and the Lobster Shack, in addition to many other enterprises in Cuttyhunk.




Our guests enjoyed their harborside meal and the champagne they brought with them so much that they ordered a second serving of lobster.






After lunch we guided them on a short walk up to the top of the Island and enjoyed the views from the new observation platform at the top of the hill.













We then returned to the sailboat via dinghy, got underway, and after motoring back through Canapitsit, we set sail and motor-sailed back to Martha’s Vineyard with a favorable returning current helping us along.







The couple enjoyed a romantic ride up Vineyard Sound on the bow.

After doing some calculations we realized that our planned return time to Edgartown wouldn’t be possible, so we made a change of plans to arrange for an Uber to pick the couple up from the dock in lovely Lake Tashmoo. They had a dinner reservation and we promised to do our best to make sure they wouldn’t miss it. They enjoyed going through the narrow entrance channel and seeing the tranquility that Lake Tashmoo has to offer.
The drop-off at the dock and the Uber pick-up went seamlessly, they made it to dinner on time and our guests were very pleased with the outcome of the day on their Martha’s Vineyard to Cuttyhunk charter.


We offer full day trips to Cuttyhunk from Martha’s Vineyard and in Buzzards Bay from Mattapoisett and Dartmouth.