This is a question that comes up quite frequently on the sailing forums and so this is copied from an earlier discussion. From reading posts and from talking to people who have done the purchase lease back or bought ex- charter boats I have come to the following conclusions. Much of this varies with the charter company and while not every boat that comes out of livery is trashed, most come out with defects, some minor, some major, some visible and some not, and some a simple product of wear or neglect that are just waiting to fail.
You have to understand how these boats are used. First off, they are out of their slips, almost day in and day out. Most are being used in the Caribbean, which is not an easy environment on boats; Lots of sun, high salinity, lots of breeze, all of which add to the toll.
They are being used by people who in the best case are well meaning and careful but are not completely familiar with the operation of the particular boat they have chartered. In the worse case, are not competent and frankly don’t care. Charterers run the gamut from people who are a bit timid and spend a lot of time at the dock, perhaps not all that well tied up and protected. To the other extreme, the people who feel they have rented this thing and by golly they will sail it or slog it at full throttle no matter how much wind or violent the waves that are out there, to every type of personality in between.
Adding to the problem is that charter boats are often ordered with fairly minimal equipment, such as slightly undersized winches, travelers with almost no purchase, the smallest self-furler that can be expected to make it through the lifespan in livery, cheap sails made of heavy cloth, and so on.
From talking to people who have bought ex-charter boats, you might expect to have to upgrade, replace or repair big ticket items such as: engines, sails, deck hardware, upholstery, running and standing rigging, instruments, ground tackle, galley equipment, as well as, the need to address a whole array of cosmetic issues. In the worse cases that I heard, there were keel and frame structural problems from (a) probable hard grounding(s), and major electrolysis problems leading to a sinking when a bronze thru-hull have up the ghost.
Now then, not every boat is going to have every one of these problems but even if there is a minor mix of some of these, it can result in a lot of long term high maintenance costs. In the end you have to ask yourself whether you couldn’t buy a solid boat, that was not in charter which has better gear and less use, for less money and a lot less effort than it would cost to buy an ex-charter boat and put it in shape.
A good friend of mine, who had gone the ex-charter boat route and was constantly picking my brain for advice as he restored his ex-charter ended up replacing an engine, sails, awlgripped the hull and refinished the interior and replaced instruments, upgrading and replacing worn deck hardware. He once said,”You know the guy who buys this boat from me is going to get a great deal.” He was probably right. The fact that the boat had been in charter will always limit its price and the fact that this guy had done a great job fixing it up meant that he had far more into the boat than he could sell her for. Perhaps, the right answer is to look for the ex-charter boat that some guy just carefully restored and negotiate hard.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay