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First of all – Congratulations to your new B40. You will like her. We kind of love ours.. Memorial day; you probably want to do some slip reservations in advance in at least in BI, Cutty and Martha’s Vineyard. We have typically anchored or taken moorings but I understand that you don’t want to do that. Otherwise Quisset is nice (but it's strictly mooring). Westport has slips but plan the entrance, the current can be interesting. Westport obviously has a really nice beach but there isn’t that much more there.

I can’t help thinking that it is an ambitious first cruise. First time we were out on our boat when she was new we were pretty much out for 2h. After that I felt that I wanted to go in and check a good number of things. That said, your schedule will probably be weather dependant but should be fine. Drop the anchor for lunch in Tarpaulin Cove on the way to Martha’s…
Have fun and best of luck with the new boat.
 

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I just saw Dan Goldberg’s (the one with the nice signature) excellent reply.. I could have sworn that BI / Cutty was more like 35 and a bit NM but maybe I’m wrong and it just felt like it. Anyhow, the comment about Eldridge is important. You will not see any tricky navigation in these waters. But the currents can be nasty in some places. Plan your trips according to your Eldridge.. Especially if you end up going through Wood’s hole, into Westport or any other tight location.
 
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