Let's start with disembarking, or leaving the dock. Depending on the size of the boat, one can do this single-handed, and that is, in fact, a skill Mike is working on, for the times when he's there and I'm not. But I'll describe a couple of ways that two people can do this. First of all, make sure dock power (if you have such) is detached, as trying to sail away with a power cord holding you ashore is just embarrassing. Luckily, we've managed (so far) to remember this step, even if occasionally it was at the last minute. You then want to make sure all docking lines (the ropes holding the boat to the dock) are free. Typically, we've had the front (bow) docking line nearest our slip (the port line, in our case) and the port aft line as the only things holding us to the dock until the last second. Mike takes care of slipping free the aft line (a simple quick tug or flick usually does the job) while I handle the bow line.
We have done this in a couple of ways. First, we can leave the bow line loosely around the front cleat and, if a gentle tug or flick on my part as I sit at the front of the boat doesn't remove it as we start out, then simply letting go and allowing the line to slip free of the cleat and dangle in the water for later retrieval will do the trick.
Second, I can walk the boat out. While I stand on the dock, I will have the bow docking line in hand in case of any sudden need to wrap it around a cleat to secure the boat (like if it starts to swing too much or if Mike suddenly decides we need to stay onshore for some reason -- like engine failure or another boat coming past or something), but otherwise, the boat is free. Taking hold of one of the mast shrouds or a stanchion (vertical metal pole that secures the lifeline -- you can see one in the above picture behind the cleat), I guide the boat out and give it a little push to keep the nose off the dock before I hop aboard. Only nerve-wracking the first time, when you're not sure whether you'll clear the lifeline or if you have a tight enough hold on the shroud to pull you on and will fall in the water or not make it on board before the boat pulls too far away from the dock.
Now, before all this has happened, back when you're removing all the dock-lines save the fore and aft ones, Mike has lowered the motor propeller into the water and started it up in neutral. Once we're ready to go, he puts the motor in reverse and we cast off. In a boat with tiller steering, like ours, things seem backwards, as when you push the tiller right while sailing or motoring, the boat will move left, and vice versa. EXCEPT when in reverse. Mike took a bit to get used to this, and we even took the boat out on a calm day to practice motor steering in the bay, both forwards and backwards. The first couple of times disembarking had us doing some interesting turns and near loops, but Mike always managed to sort things out, though he felt bad about his mistakes for awhile. Until we watched other more experienced sailors occasionally having their own spot of difficulty. Then he felt better.
Like when Bruce took his boat out for a little spin and misjudged the turn as he reversed. He also saved it from any crashes, but the gentle sound of "Fuck!" drifting across the water over the sound of his motor made us smile in appreciation. His boat has a steering wheel rather than a tiller, so reverse is like in a car; opposite to the direction you're steering.
Mike brings us around to our slip by nearly going past it in order to make the turn in as straight as possible. We did start off going a few boat-lengths past our slip and then turning around, as suggested by other sailors helping us to learn, but now we've progressed to turning right in. He will have the aft line ready to slip over the cleat as he steers and then cuts the motor to keep the back of the boat from swinging around.
I, meanwhile, have jumped off the boat onto the dock with the bow docking line in hand. I wrap it loosely once around the mid-way cleat to keep the bow from veering too far and to hopefully keep it from smashing into the front of the dock. Depending on how quickly Mike has cut the engine, or how fast he entered the slip, this hasn't always worked as expected, but we haven't done any real damage to the dock. The boat's made of sterner stuff. We have occasionally cut it a little close and so perhaps added another fender near the front just to make sure no unnecessary scraping occurs on the boat. It is difficult to really see the dock when you're trying to line up a 26' boat next to it, so judging how close to put the nose is a bit of a learned art, and one Mike is learning well. I try to help with hand motions, but sometimes my observations from the bow don't quite line up with the dimensions of the side of the boat. But then, that's what fenders are for, right?
Once the boat is in a good position, Mike will secure the aft line and I will move my line from the mid-way cleat to the forward cleat and secure it there. We attach another dock line to the front so that it has a line running from the port side and another from the starboard. We also use one or two spring lines for added stability and to keep the boat from moving forward and backward, as the front and aft lines keep it from moving sideways away from the dock. If we use two spring lines, one goes from near the front to the mid-way cleat on the dock, and the other goes from near the aft to the same cleat. It might be overkill, but that boat's not going anywhere.
Again, it's all a learning process, and watching others is often just as gratifying as doing it yourself, especially when they make equally bone-headed mistakes. Like the boat that bounced off the side of their dock before swinging around to try it all again. Or sailing past your row of docks because you're new to the place and didn't recognise the right entrance at first (oh wait, that was us on our first return). My favourite is the slip with a line of swimming noodles strung all along the inside of the dock to protect the boat; I've considered getting some of our own and doing the same thing ...