The Roberts 53 that you are considering would be just about the worst choice you could make for a single-hander. Not only is it a very high displacement for single-handing, but it is also a very high windage and very high drag design. Windage makes docking much more difficult, and high drag requires a lot more sail area for any given condition. Fitting out a design like this for single-handing would be wildly expensive as compared to a more suitable design with equal accommodations and seakeeping ability. You could easily spend as much adapting a boat of that general design as the entire cost of buying a more suitable design ready to go.
If you were a very skilled single-hander, you would know how to pick your timing and when to wait things out. If you were in great physical shape you might be able to handle a design like that in moderate conditions or in heavy conditions for a reasonably short period if nothing extreme went wrong. If you were lucky, you might never have to find out whether you can deal with a boat that big when all hell breaks loose. But for most of normal folk, the goal is to try to stack the deck in our favor.
But I doubt you are a very skilled single-hander or you would not be asking this question since a skilled single-hander would know the answer for themself. Picking a worse than mediocre design for your announced intended purpose (single-handed circumnav), being finished by an amateur boat builder without the experience to know what has worked for them in the past, and trying to adapt a totally ill-suited design for the purpose would be clearly stacking the deck against yourself and against the kind of common sense understanding of the physical realities of distance voyaging that a circumnavigator needs to have.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay
Last edited by Jeff_H; 11-09-2011 at 10:59 AM.