Thanks folks, really great replies. The thing I like the most is that NOBODY suggested I'm too new at this to single hand. I was half expecting that. So I guess there is no reason not to get out there! Although to CaptnRon's point, I think I'll get that autopilot sooner than later.
You'll learn everything faster that way!
I bought my Catalina 27 four years ago after taking the ASA class and possessing some minimal experience with a sunfish as kid. It was an old junker that I'd figure I'd just have fun with. I took it out alone on a windy day in October and you can say from that day on, I learned to sail the hard way.
The most difficult part was keeping the boat head to wind or tending to the sails without an autopilot. The steering wheel brake was worn out but even if it was effective, once the wind filled the sails, the boat would spin off in some direction I did not want to be pointed in! Raising and lowering the main became a headache as soon as the boat was no longer headed into the wind. I'd often find myself tacking in circles!
I don't remember too much about the second year sailing but after that winter, I spent two grand on an autopilot, including installation (it was nothing compared to the money I had already spent on new sails, cushions, lifelines, running rigging, docklines, fenders, other electronics, you name it!).
By the third year, I had my AP installed by the spring launching, and I don't know how I ever sailed solo without it! Tacking is a breeze. You simply press two buttons simultaneously to tack the boat through ninety degrees. After you release the two buttons you quickly press the +10 or -10 buttons about seven or eight times to make sure you don't come out of the tack pointing too high. As the boat comes head to wind, you can work both jib sheets like a trimmer on a race boat and then, as the boat speed picks up, you can pull the traveler back over to windward again. By then, you are going fast enough to hit the opposite + or - 10 button about three times or so to be on a close hauled course and you can fine trim the sails or your course.
Of course, having the sails out of balance can overwhelm the autopilot, though on gusty days you can simply work the traveler while the AP does the steering. The only down side to using it is the noise of the steering mechanism which can be really annoying at times. Otherwise, I'd have it on much more often.
I would also suggest having lazy jacks. They make dropping the main a breeze! I simply turn the engine on, put it in gear, set the auto pilot so the boat is pointing up into the wind, tighten the topping lift and the lazy jacks, and release the main halyard while standing at the mast to assist gravity in getting the sail down. I then put a couple of ties around the sail and boom, and I'm good to go (home)!
Sailing alone, without a doubt, is a great pleasure. Don't get me wrong, I enjoy going out with different people, experienced and not, however being by one's self has some great advantages: There is no one to tell you they need to be back by 3:00, or no one who can't tend to the jib sheet because their wife is calling them on the cell phone. You don't feel like you are bothering your crew if you need someone to pull in the sail another half of an inch more, or worst of all, you have to clean the head again because someone decided they had to go potty just before a gust of wind suddenly heels the boat to the rails! Most of all, I think I really get a kick out of out-sailing other boats around me, knowing that I am putting up one hell of a good fight without another soul on board to help!
If the wind is coming from the west, I often find myself getting a little docking anxiety ahead of pulling in. The west wind, if it is strong and the tide also not in my favor, will push the bow of my boat away from my dock, crashing me into the yacht on my starboard side if I do not secure it quickly enough. I've become proficient in using propwalk to my advantage, but I still remain concerned when the west wind is strong.
This year, I also started crewing on a J105 once a week for casual racing. It gives you a different perspective plus its nice to go on a boat that isn't yours for a change. (No headaches if something important breaks!)
Afterthoughts: I have enjoyed the last few days of autumn lazily sailing under genoa alone.
I also have been lucky to sail about 3 or more times a week this summer. That would be impossible if I had to depend on crew showing up!
My next boat will have end boom sheeting to make it easier to work the traveler/main without having to engage the AP.
