Re: Cruising Skills/Practice
There's going to be lots of stuff you need to do that's outside your current envelope.
Take experienced crew with you, get in over your head and get it sorted while you have some help.
Sail in conditions that you'd never think of single-handing in, check the weatherhelm & figure out how to get the boat to self-steer for even 5 minutes.
Learn how to back the boat upwind, downwind, cross-wind. Learn what's possible & what's difficult.
Figure out 2 or 3 alternatives to conventional actions. Your anchor is probably on the bow. Why would a single-hander go way up there to anchor the boat? Figure out another way to do that.
Plan on 24 hours (or more) of fog. Are you going to sit there with a fog-horn all night? Assume that you GPS will not receive anything useful in the fog - it's happed to me in CT.
When all else fails, then one more thing will too.
It is by Will Alone I Set My Ride In Motion.