I purchased an old/used 20 footer (Southwest Explorer) about 6 weeks ago, having never sailed anything more complicated than a Sunfish. Between my work schedule and crappy weather, I finally took her out this past weekend. It was NOT PRETTY! First, after struggling to raise the mast by myself, I realized a sizeable limb from gum-ball tree was hanging about 25 feet over the boat ramp ...just low enough that my mast couldnt pass under it. So I had to unhook the trailer from my truck, drive home, get a ladder and chain saw, return and cut down the limb. I should have realized that this was an omen.
While I understood the mechanics of raising the sail, I struggled to get it done with the boat floating in open water. Rather than point IN to the wind, as soon as I turned the motor off, it immediately turned stern to the wind. So I fired the engine back up and got my wife to tend the tiller while I attempted the mainsail. Is there supposed to be some device/method to keep the sail slugs above the slot where they enter the mast without raising the sail? The sail was flapping in the wind as I worked feverishly to insert each slug. But I got it done.
Speaking of the wind, I guess I need to say that I greatly underestimated the force of "20 MPH Gusts". ...which the weatherman nonchalantly added as an addendum to his report of 10-15 MPH westerly winds.
As soon as I had the sail up, one of those gusts caught me offguard, snapped off a couple of the sail slugs on the stern end of the boom and nearly capsized us. Did I mention that I forgot to lower the swing keel before raising the sail?! (I put that on my mental check list for next time)
...and that my halyard magically got tangled in a knot and wouldnt pass thru the block to let out the sail.
My wife says she'll ever go out with me again.!! ...so I guess it ended up being a good trip afterall!
Greetings fellow Sunfish sailor who moved to cruisers.
I sail single handed a lot. I have some tips for you.
Keep the motor running and in gear when you raise the sail. I don't turn the motor off until the sails have filled or I'm off the wind enough that I can just pull in the sails and be on my way.
If you've a tiller, tie it off. I have a boat with a tiller that has a cleat on the underside of the tiller. It makes securing it a breeze.
The wind will blow the bow around so you may need to make constant corrections. Hoist, bring her back into the wind. Hoist some more, bring her back into the wind. Sometimes you hit the sweet spot, sometimes not. It just makes you appreciate a crew.
I lower the centerboard first, then move to the sails. Look around for other traffic. Very important!
Get as much done as you can before leaving the dock. This includes any preparations you need for returning. You need everything at hand. You won't have time to search for the winch handle, search for the boat hook, hank on the jib, etc.
Lead as many lines aft as possible. The only reason I need to go forward is the sail ties and I'm going to solve that with some EZ Jacks. Leaving the cockpit is the dangerous part when you're single handed.
Check out some youtube videos on singlehanded docking. I use a line around a stanchion lead back to me at the cockpit. I can use it to snag a dock cleat, tie off onto the rear deck cleat, put the motor in forward and she snugs up to the dock until I get her more secure. Learn how much momentum you've got and at what speed you lose the rudder as it'll help. Mine can be moving pretty slow and still have a working rudder. Sure makes it easy to stop her at the dock.
One of the biggest things-start on lighter days until you get your ritual down. You'll get there. If you've been sailing a sunfish then you know what you need to know. You're just learning the boat right now.