Re: Question for those who sail cutters
We have a sloop with a baby stay and running backstays which we only used on our 1700 mile delivery trip from Florida to New England. The baby stay was rigged for the offshore segments and turned the boat into a cutter.
We didn't have much of a problem tacking, but we didn't tack all that often, either, so the cutter rig is probably easy enough to handle on a long passage.
On the other hand, I've got several months' experience sailing cutter-rigged Island Packets in New England and the Virgin Islands. The Island Packets were not impressive for short-tacking. About a quarter of the time, the genoa would hang up in the slot. There were a couple of times when I turned the motor on to pass through the wind, which had as much to do with the modified full keel configuration. There is probably a learning curve for tacking a cutter rig, but it shouldn't be that big a deal.
That said, the cutter rig can be more comfortable (and stiffer) when the wind picks up, so it is all a matter of boat design compromise. I would disagree with an earlier blogger that the aerodynamics of a cutter rig are much different that that for a sloop. You need to manage the slot between sails in either case. In a tradewinds area, I would find the cutter to be worth consideration. In lighter air, I'll stick with a sloop rig.