Advice for Mystic CT, Newport RI, Montauk NY

[Kikaboo]

I am planning a 10 day trip @ approx 335 total miles and I'm looking for some advice as this will be our longest outing yet both in time and distance.

Regal 32 Express: I will be traveling from Long Island sound, 1st stop is the base of the CT river. This I have done before so I know what to expect. Then traveling up the CT river, not sure how far I'll go but I am not concerned with this either.

However, from the CT river I will be traveling in unfamiliar waters so this is where I have questions.

Heading to Mystic CT, then Newport Rhode Island then Montauk NY. We may also stop in Block Island.

Over the 10 total days, I am bound to hit some less than ideal weather/conditions. Normally we boat in conditions that are pretty favorable so I don't have a lot of rough water/bad weather experience. For those of you that boat around Mystic/Newport/Block and Montauk, any advice you can offer? What to watch out for or avoid? For example 25+ mph winds out of the East, etc

Thanks