A Custom Buzzards Bay Sailing Charter: Eel Pond, Hadley Harbor & More

We completed a great half-day sailing lesson and cruise for three women which included sailing across Buzzards Bay from Mattapoisett through Woods Hole passage. These adventurous guests wanted to take the helm themselves and spent the day learning the nuances of sailing a ketch-rigged, larger cruising sailboat—an experience perfect for anyone seeking a hands-on private sailing charter in Buzzards Bay.

Sailing under the iconic drawbridge into Eel Pond offered a memorable pause in the heart of Woods Hole, a picturesque village in Falmouth on Cape Cod known for its historic waterfront charm and vibrant marine culture. After leaving the Pond, we sailed through Woods Hole’s Great Harbor, admiring grand waterfront mansions and the distinctive houseboat community—all from the cockpit of our own 42-foot sailboat.

We then crossed back through Woods Hole passage and explored Hadley Harbor, one of the best hidden secrets in the area where Buzzards Bay meets Vineyard Sound. Accessible only by private boat, this secluded anchorage is part of the Forbes family’s estate and remains one of the most stunning and little-known destinations near Cape Cod and Martha’s Vineyard. Our guests were delighted by this hidden gem—an unforgettable stop for anyone seeking quiet beauty and a break from the busy summer coastline. It’s the perfect place to anchor, go for a swim, enjoy lunch, or simply soak in the peace of protected waters.

With the wind at our backs, we ended our day cruising smoothly toward Mattapoisett Harbor, wrapping up a custom charter that blended learning, exploration, and relaxation—hallmarks of every Buzzards Bay sailing experience we offer.