You have given an exact description of my
Pearson Ariel, and all of its
docking challenges. I too sail single-handed with the same
docking anxieties.
Here are some things I've done:
1) Install fore and aft docklines that are as long as the
boat. Shorten the bow line so it is just-short-enough to not entangle the prop if it goes
overboard. Now you only have to worry about a stern line entanglement. Leave the bow line always on the bow cleat and tie it up somewhere aft when underway. Rig the stern line just before coming into port. Stow it carefully so it doesn't go
overboard and entangle the prop. Now have both lines in your hand as you approach the
dock. If your boat is like mine, it has minimal astern
propulsion because the prop is just blowing
water against the
rudder and
keel when in reverse. I can't count on reverse stopping me in the slip. Instead, I hop off as the
cockpit passes the end of the slip and use the bow line to stop the boat. Yes, it looks comical, with me sliding down the
dock with the bow line in my hand. But even though my boat weighs in at 6,000 pounds, I've never dislocated a shoulder. I leave the
engine idling in forward
gear - just in case something goes wrong - so the boat doesn't back out of the slip without me. I have done this literally hundreds of times with no mishaps. it's just best not to have an audience.
2) Have an
anchor ready at the stern at all times when in a harbor. If the
engine quits, drop the
anchor with enough
scope and tie it off. Now you can troubleshoot the engine at your leisure. There have also been two occasions when my engine failed to start when returning, and I approached my dock under sail from directly upwind. I can't let out my main boom without whacking a piling. When 60 feet out (the
water depth is 10 feet), I dropped the stern anchor with a trip line floated to the surface on a
fender. I took in my main. I then let out the
rode to slowly enter the dock. I later retrieved the anchor with the trip line. This works if there's enough
wind and you can approach from directly upwind.
3) If you have tiller
steering, practice sculling in no-wind conditions. I once sculled a mile in calm conditions when my iron sail failed. It took 4 hours, but I made three 90 degree turns to enter my slip.
4) My Carl
Alberg designed Ariel is notoriously unsteerable in reverse using the
rudder. The rudder is truly useless at anything below insane speeds. Fortunately, I can twist the engine 45 degrees or so in its port to steer astern. If you can spin your engine in its engine port, I recommend doing that instead, and just hold your rudder amidships.
5) Try to always approach your slip from directly upwind. You can then approach at minimal speed since you'll have a minimal need for steerage.