Why do I feel like the OP is a first-time author planning to write a book?
Long Island is pretty much a hundred miles long. City Island is pretty much at the west end of it,.... Two hundred extra miles in a small boat. Hmmmm.
Ha, you're wrong. I asked the question because I have been on this site long enough to know that there would be plenty of varied (and even conflicting) opinions. You have proven that old adage that compares opinions to butts.
I knew that there would probably be people saying, "Oh my, the East River? Ferries and barges and closings along Roosevelt. Currents and tides and old pilings, oh my! No, going the long way up the Long Island Sound is worth the extra time it takes."
Then I knew there would be people who would say, "Nah, no worries, go south, it's an adventure."
I don't know if you have read the posts in this discussion, but two people said that they have gone the northern route, up the sound. Presumably they did so because the longer distance seemed preferable to navigating the traffic along the river route. One person actually said he prefers the longer route. I asked, because I've never traveled through there, and I wanted to know what to expect. That seems unreasonable to you?
And, then there were people who gave me great information on exactly how to make the passage and what I can expect. Your response was actually the only one that didn't offer much helpful information at all. I guess you haven't noticed that I've been a member on here for over two and a half years and have been actively involved in sailing discussions. And, when I write my book, it will be based on things I've actually done.