In response to your navigation question. I think a way to quantify your "sail well left of the target" scenario is to imagine a line 90 degrees to your course. I'm assuming here that you're pointing as high as you can, which begs another question, do I sail slower toward the target, or faster slightly away from the target (which I'll address in a minute). When, and only when the 90 degree line of your next imaginary tack intersects with your destination should you even contemplate tacking, unless seaway, draft constraints or other external factors impinge on the decision tree. Given that most sailboats tack within a few degrees either way of 90 degrees, it's a good rule of thumb (actually more of a guideline). Other factors will affect the 90 degree "rule", such as tide. Once I factored for slip with a lee shore situation, and the tide took me upwind until I had to dodge the upwind shoreline. Being an eternal pessimist, I usually sail well past the 90 degree line, which usually does two things. It allows you to almost always hit your target as planned, and if you're a tad upwind, you have some wiggle room if you need to fall off to avoid things like powerboaters, etc.
Back to the question I raised about close-hauled vs. close-reaching. If you're going 8 knots for one mile, it'll take you 7.5 minutes to get there. If you have to travel farther to go faster (i.e. fall off), and that gets you up to 10 knots, that'll get you 1.25 miles in the same amount of time. So, depending on the math it often times is better to sail farther out of your way to get to your destination, and we all know that faster is more fun. I've had to break myself of the habit of pinching my tacks to sail in as straight a line as possible to get to the destination, and I'm often times passed by people sailing apparently way out of their way.
With regards to your second question, I too have had trouble sailing in and out of fairways to get to the ramp. Most notably in Laguna Madre while barhopping Padre on my Getaway. I'm glad you have the right attitude about it being a learning experience. I would try heaving to, meaning tack the boat without bringing the jib across. That way, you have some lift from the sails, but it won't get away from you, and when you do clear whatever obstacle you're trying to get around, you're a lot closer to sailing than if you had to raise the sail, which means less drifting while you're hauling. This is a theoretical suggestion only. I can already see that part of heaving to is pushing the tiller hard over, which will certainly affect tracking and make paddling more problematic. I will be trying it soon myself for the first time in the next few weeks.
Concerning priorities:
1) Safety of captain, crew and others
2) Safety of boat and other property
3) Physical obstructions (i.e. daymarks, lee shores, boathouses, docks, piers, boats in their slips, downed skiiers, etc. This sort of blurs into the previous two.
4) Comfort of your crew. If you're sailing with a bunch of newbies and you fly a hull, some of them may not come back. I often use a potential spilled beverage as a litmus test for sailing with newbies. Once they get comfortable, then you can fly a hull.
5) Efficiency of sail (i.e. proper sail trim, sailing toward your destination, etc.)
I always say that sailing is easy, sailing well is hard. I also think that besides the obvious, being a good captain is making sure everyone has a good time, regardless of how technically well the boat is sailed.
My $0.02,
Chris
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