Join Date: Oct 2009
Location: Gloucester, MA
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Yes, cutters are good boats for singlehanding. There are a few important things that will affect how easy they are for 1 person.
The cut of your yankee is very important for tacking. If you get a 140% genoa, it will get fouled on the inner forestay and make tacking hard but a good 100% yankee will tack easily.
Your boat can be setup with a self tending staysail or not. I don't know of any club-footed staysails that are not self tacking. A loose footed one is much harder to set up to be self tacking but it can be done. Either one can be set with roller furling but you will need to have an adjustable outhaul with the club-footed sail.
Having all of your lines lead aft is definitely helpful. If the deckhouse layout is correct, you can do this but it will require some time and money.
Having a way to lock the helm if you need to go forward is important. This can be a simple wheel lock or an autopilot. Being able to set the rudder for long enough to run forward and then back to the cockpit is very important.
You should not be worried about gybing either with a cutter. Some cutters will actually have smaller mains with makes them easier to gybe. To keep the staysail from slamming, you simply sheet it hard and gybe normally.