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Old 01-13-2012
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There is no single right answer without more specifics. Traditional small working water craft with rigged as gaff rigged multiple headsail sloops and gaff cutters have worked offshore for centuries, some more succesfully than others, my point being that there is nothing inherently unseaworthy or dangerous about a gaff rig. But there are also similar length gaff rigged race boats and coastal cruisers which are less suited for offshore work due to the hull design, deck layout, and the specific design of the rig itself.

Then there is the simple "how lucky do you feel?" risk management issue. Boats of that era rarely had the safety features the court of general opinion would seem to deem as essential such as self bailing cockpits, lifelines, standing backstays, and quick release mainsheet cleats.

And there is also the issue of the boats structure. While none of this may apply to the boat in question, in most cases the reason that a wooden boat is fiberglassed is that the boat needs to be refastened and recaulked. In boats of the age of this, it typically also means that the boat has been refastened so many times that she needs to be reframed. There are a lot of ways of fiberglassing a wood hull but most are not great long term solution. Depending on the conditions the stresses of sailing offshore can be no dofferent than inshore sailing, but they can also mean a lot higher and more frequent stresses. While these may not sink the boat, the repetative nature and higher force load, can shorten the lifespan of the boat as questionable fastenings work more, or the bond between the planking and the skin is flexed and stressed.

Jeff
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay and part-time purveyor of marine supplies
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