I regularly single hand my boat which is a 47''cutter rigged sloop. She grosses out at some 37,000lbs. She has all
furling sails and everything runs back to the cockpit. The times where extra bodies come in handy are when docking and anchoring. However it is amazing what you can do with a properly
prepared spring
line and I never hesitate to ask for help on the dock if I feel uncomfortable with conditions. When anchoring, I prepare well in advance and will have a proper amount of chain on deck prior to reaching my chosen anchoring spot. Using a trip
line,which I run back to the cockpit, I can release the
anchor right from the cockpit or I can use the
windlass since I have a switch for it in the cockpit also. Retrieving the
anchor is also done from the cockpit by using the
windlass once again. The greater issue however, is the ability to maintain a proper watch--in spite of all the
furling gear,
autopilots, self steering gear and electronics this is the greatest challenge to any singlehander and it really has very little to do with the size of the boat. I guess one could make the argument that the larger the boat, the more potential for fatigue and therefore it becomes more difficult to maintain a proper watch. However, in my opinion, a relatively large vessel can be equipped for single handing ie. the various around the world alone races,
but one really has to wonder as to what kind of watch is being maintained.