Join Date: Nov 2009
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I am not sure why everyone wants to talk you out of this, but your plan seems pretty focused and doable with the right amount of money. I don't think your boat will rot while sitting as long as it is put away correctly and checked often enough to catch problems. The LI season is most likely May to October in the first place, so 6 months average. Most people don't use the boat often in the early season or late season, so four months reality. During that time, many people sail a few days a week and maybe a week cruise, so 4-6 weeks. There you go, you just want to compress the season.
You can ask for specifics to the LI area here or on other boards. If I were you I would be asking marinas with maintenance and storage yards this question. They will tell you specifically what it will cost to launch, pull, and store the boat for whatever period you want the boat in the water or on the hard. It does not sound as if you want dock space as you will be cruising. In that case the costs will be X days times whatever the transient rate is in the area, whether that be mooring or dock. Subtract # of days at anchor.
Maintenance will be your big issue if you want a professional to prep the boat for launch or de-commission the boat at the end of the season. If they don't do it your season will be compressed even more while you do it. The benefit of early launch and late season is prepping the boat when the weather is crappy.
With all that said I don't think that this will be much less, in terms of dollars, than a person who has an average season. Your costs for dockage will be less (not sure in your area how much), but boat costs of purchase, launch, pull, and maintenance will be very similar. If you are having someone else do all of your maintenance it will probably be more expensive.
I am not sure how restricted you are to being in the LI Sound for this cruise period. I would agree that time share would not work, as the season is too short and you will probably want the best weeks. However, chartering should not be ruled out. You can charter almost anywhere in the world, whether that be in the Chessy, on the east coast, Lake Michigan, the North Channel of L. Huron, BVI's, Greece, etc.. You are talking about a one time travel for a 4-6 week cruise so the travel costs should not be high whether you drive or fly. In most fleets you can negotiate a better rate for a 4-6 week cruise and that can be 15-30% dependent on where you charter and the dates of that charter. When you charter the boat cost is the charter cost, the maintenance and storage is not your problem, and when the charter is over you walk away and don't have to worry about the boat the rest of the year.
I don't think you can accomplish what you want for less dollars then the charter costs, as a less expensive boat will just mean more maintenance costs. Why not get a relatively new boat to charter and not worry about it?
Whatever you do, welcome back to sailing.