That’s a great trip. I remember when you were talking about making it last season. Keep in mind though that the South Shore of Long Island is very different than the North Shore. I’ve got no experience with Shinnecock inlet, or east of the Great South Bay for that matter. The furthest east I ever go is Fire Island. But if you make that trip and decide to run inside because of weather or the need for fuel just beware that the bays between the barrier Islands and Long Island itself are very shallow with narrow channels and zero room for error. It’s well known that Moriches Bay requires local knowledge to pass through without running aground. One of the big reasons I don’t go there. Well that, and I like the city better. Lol! Most people I know that regularly head east avoid Moriches Bay altogether, or call either Boat US or Seatow to talk or guide them through it before they go. I’m very familiar with the 3 most West inlets (East Rockaway, Jones, Fire Island) and go in and out of them fishing on a 22’ boat. But if you’re unfamiliar with inlets in general and need to go in or out of them, just be sure to give them some respect. They can be like going through a whirlpool at times. Slack tide would be best for a first timer. Once you do it a few times it will be no problem at all in your boat. BTW: If you do make the trip, you should do at least an overnight somewhere on Fire Island if you’ve never done it before. Both Sailor’s Haven and Watch Hill are Federal Parks so no problem with not being a resident of a particular town in order to use their town Marina.