I've done it but it has always been on a bigger boat (generally 40+ feet). I only have a little boat these days (23) and quite frankly would only feel comfortable making the run offshore on a perfect day.
I plan to spend most of my time "inshore" fishing this year but if I hear some big game fish are in close, I may pick the day and go for it. Like most boaters we all have weather stories, I just don't want to re-live any of them.
But a nice summer day with no bad weather in sight...running 25 or so miles south of the vineyard to tie into some tuna or maybe mako for a few hours..yeah, I'll give it a go. But thats about it for me, until I get that 45 CABO.
I'll have my year to the ground out here.
It sounds like your gearing up to go. Let me know how you make out. There is nothing quite like the sound of the drag big international screaming under full load. Every fisherman should experience that at least once....
( Having never done it before it might pay you to do a charter out of montauk and watch what he does and ask a lot of questions. )