Long Island Sound bareboat options

[Jughead135]

Starting to loosely plan a trip in/around Long Island Sound. Finding charters in "Newport" (in quotes, because it appears most of the allegedly Newport locations are actually in Providence or Warwick), but that's about it. Not automatically against it, but that may cost us a day or two at desired stops due to geography--so hoping to find other options.

A couple "must stops" are Sag Harbor and Port Jefferson. A few points further west and/or on the Connecticut shore (if we have enough time) would also be welcome. If we're going to/from Providence, Block Island would be a no-brainer.

So, three general questions for the group:
1) Suggestions on where to find a bareboat? Sag Harbor or Port Jeff would be ideal--but anything on the north shore of eastern LI would be great.
2) Time of year/seasonal considerations?
3) Anything to add to our "must stop" locations? Great place to visit, or anchor/moor/dock, or any other reasons--love to hear opinions, please!

Thanks for any info/advice!!