The end of September and the first part of October can be great for boating, both on the Cape and at Winni. We plan to leave the Cape and take the boat to Winni within the next couple of weeks!
If you can sleep on your boat there are plenty of great options for a Cape tour. Or stay at a place in the harbor. If you launch in Buzzards Bay you could easily do both the Vineyard and Nantucket if you choose your trip according to the weather.
If the wind is out of the typical SW, you may not want to try to return to Buzzards Bay from Nantucket. Vineyard Sound, on windy days, has been described as navigating in a washing machine. Sorta like Weirs Bay on a sunny Fourth of July! But if you are able to pick your days, Nantucket/Edgartown/Oak Bluffs/,etc. would be a nice trip.
I am very familiar with all the waters around the Cape so don't hesitate to PM for specific information.
Good luck!
Peter
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