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Nika -

great news on the new boat! some time ago when I had time, I started a blog and posted all about Block Island, MV and Newport. See the link below for more info on that.

I would narrow down your ports as it seems like you may short-change yourself a bit. CuttyHunk is nice but its a very small Island with not much to do there - very beautiful and a great place to spend the night but you might be pressed for time. I did BI to MV <Vineyard Haven> in 10 hours. Its difficult to get through Vineyard Sound if the tide / current is against you so you may loose some time - and it was against me.

I would do BI to MV to Newport and then home. Sounds like your boat should make it through Vineyard Sound under power with little effort which is important. My Catalina is a bit underpowered and that was a challange for me.

I am not sure what type of Island activity your looking for but each place offers everything from a quiete anchorages to busy nightlife. Do some research on MV so you stay in the right harbor that offers what you want. Good luck!

Also - from where you are in CT, you should considor a cruise over to Greenport, LI. very nice facility they built there recently and you can walk to some great restaurants and shops. I am suggesting this as a seperate trip altogether from your planned trip above.

Your Worldwide Cruising Guide
 
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