Our first request is to solicit your expression of interest.  Please complete the form HERE so we may have a better idea of what to expect as far as participation.

We are working on a 12-day itinerary beginning the cruise around September 23 and finishing October 4, 2026  We will be cruising the wonderful islands found in southeastern Massachusetts. Starting in Newport we will sail to Cuttyhunk in Buzzards Bay.  Buzzards Bay, Martha’s Vineyard and Nantucket in September is an incredible experience. Here’s why:

September often brings consistent southwest winds in Buzzards Bay and the South Coast, perfect for smooth and exhilarating sailing. The summer heat lingers, keeping the water temperature at its warmest.  While hurricane season is still active, early fall typically sees calmer and more predictable weather than mid-summer. The peak tourist season has ended, so harbors and anchorages in Edgartown, Vineyard Haven, Menemsha, and Nantucket Harbor are less crowded.  Finding space at popular marinas like Black Dog Wharf or Nantucket Boat Basin is much easier and you will have your pick of moorings in all locations as well as more anchoring room.  September brings crisp air and beautiful sunrises/sunsets that enhance the dramatic shorelines.  Migrating seabirds, seals, and even the occasional whale add to the experience. Enjoy Martha’s Vineyard & Nantucket’s Quaint Villages strolling through Edgartown, Oak Bluffs, Vineyard Haven, or Nantucket Town without the summer crowds.

September in Buzzards Bay, Martha’s Vineyard, Nantucket and Cuttyhunk offers the best combination of great sailing, beautiful landscapes, and peaceful exploration.

Please complete the expression of interest form as soon as you are able.  If  looking to charter a boat for the cruise please indicate, as chartering may determine whether we begin the cruise in Newport.  If you have any questions about the cruise, please contact Ray Cullum at raycullum1@gmail.com