haha sorry but that is exactly what I am NOT trying to do. Remember, the whole point is to get some offshore experience. The lack of very close harbors if something goes wrong is a part of that. I will bring my tools/sail repair kit and be careful about the weather, but the whole point of this exercise is to get some experience away from shore/harbors.
My main concern, frankly, is hitting something and holing the hull miles from shore, esp since I have no liferaft. Are there any recommendations for what to carry in such a contingency? I have seen the yachtworld videos about putting a sail over the outside of the hull (harder than it sounds apparently), and about trying to stem the flooding from the inside as well, but is there anything I can carry with me to temporarily plug a hole if it were to happen?
Going outside is no big deal, as I mentioned before. As far as hitting something hard enough to do damage, the chances are really pretty low but you should, of course, have plugs to fit all your thru-hulls, attached so as to be available immediately as well as some big tapered plugs (I made some up to 4" on the big end). As far as fixing a large hole, it's really a punting situation, depending on if you can get to it/how big/how many pumps you have, etc. There's an old way of getting to one from the outside with a tarp that has lines long enough so as to be able to possibly get it under the boat and over the bad section. Seems like it might work. You should have 2 manual pumps, one in the cockpit and another accessible from below in the cabin in addition to electric bilge pump(s). One thing to check before setting out that there is nothing to obstruct the pumps that might get down there when the boat is tossing around. Stuff like paper can completely plug pumps.
Remember that in the afternoon, the onshore breeze can really kick up, sometimes 25 knots and better if the temp differential is big enough. So stay far enough out so as not to be driven up on the beach. Getting too close to LI can also put you in the lee of the island if there's a nice NW wind. I would stay at least 5 miles out with your boat. Maybe somewhere 5-10 miles out. Just leave Ambrose at an angle offshore and then parallel LI. It seems like the prevailing afternoon SW tends to run more SSW along the shore of LI, tending to set you on a reach rather than a run. Much more fun.