How much does it help to have done it before?
A lot but not everything. You learn a lot about your boat just doing daysails and overnighters on the hook or slip. I love repeating some of the same daysails up and down the Hudson. I also love the challenge of rounding Manhattan up to the Sound on out. I tend to learn more when I push the limits of my sailing area. There is a lot more weather, current, shoals, rocks and waves out there that I have not yet met (I know what I dont know, ya see?). I think there is something to be said about desire as well when making a several day committment to a cruise. You have to want to do it good, bad and ugly and be able to deal with the logistics of it. There is something to be said about perseverence as well in that once you are committed you must be prepared for most of the possible outcomes (alright ALL). This may mean warm clothes, foul weather gear, good ground tackle, the list goes on (this is the stuff that makes me crazy. Do I have the kitchen sink?), and you shove off.I had a nice sailing season last year but two trips I took stretched my boundaries a bit, so to speak. One was leaving the Great South Bay on an ebbing tide which turned the normally complacent 4-6' swell into 10' crests. Once we got past the mini race caused by the tide the Mac 26S cruised over the swell just nicely, thank you. We passed Jones Beach where there was an air show going on and F-1X jets roared over us in formation. We had nothing to fear from the CG as the Navy was already there in the air (we had no life raft which is req'd for outside Colregs demarcation line 32.6.41 etc).The other trip I took around Manhattan and we got hit with a thunder/lightning storm in the East River that rivaled some fireworks displays. We were near the Whitestone Bridge when it got scary and the wind picked up considerably as did the lightning. I had read quite a bit about lightning on boats and there are no clear reccommendations as to what to do except to wrap yourself up inside the rubber inflatable in the cabin. I was with 3 friends who are all good sailors so I left the cockpit and rain so as not to confuse things or get in the way and I decided to eat the last half of my sandwich while the wind whipped the boat and the thunder bellowed around us. What I was doing was trying not to panic and stay out of the rain I suppose. The localized thunderstorm eventually moved off as the booms of thunder and flashes moved farther away. The wind subsided and we had passed through Hell Gate and into the western LI Sound. We did our 50 mile sail in 10 hours or so in a 26' boat and lived to tell about it.Regarding experience, would I go out Fire Island Inlet on an ebb tide with a strong north wind ever again (we had almost no wind meaning the high waves were far enough apart)? Probably not if I could avoid it. I would rather wait for the tide to turn towards slack. Would I go eat my sandwich in the cabin again in a lightning storm? Most definitely. We could have pulled into some small anchorage under an unsafe speed as we had not reefed the main but the owner/captain decided to press on and the storm was short lived and we are still here. Hey, that is one thing I learned from reading books: "Quick to blow up, quick to blow out." or something like that. I guess what I am trying to convey is as other posters have already said is that you learn something every time you go out if you are paying attention but I find myself paying attention a lot more if I am going somewhere I dont always go.Experience is also like a Catch 22. You can read all you want but you will never experience it for yourself unless you actually do it; otherwise it is just a dream. Do it now or, er, soon!Good luck with all your projects.CalebD