Some of my sailing friends are surprised that I can sail alone, but it really isn’t much harder than going out with a crew. The biggest difference is always having to think ahead many steps and get everything set up well in advance of when I might need it.
With a crew, you can wait to do a task. If you need to get dock lines set up to tie up at a guest dock, you can do that just before you approach the dock and decide then which side you need to put lines. If you are sailing solo, you will want to allow time to set up dock lines long in advance in a relatively calm place with no traffic, and have lines on both port and starboard, just in case you can’t tie up on your first choice of sides.
When I go out alone I try to get as much set up before I leave the dock as possible. I put dock lines ready if I’m going to tie up at a guest dock at my destination. I get all the lines I need to open the main sail and the jib on the winches and set up. I tie a portable radio to my life vest in case I fall overboard and make sure all the safety gear on my boat is in place and working. Once I cast off, there is little left for me to do except raise my sails and head for my destination.
The biggest challenge may be tying up at the end without help. The most efficient way to dock is to have one person at the wheel keeping the boat in position and a second person getting all the dock lines tied up. Single handed, that can be quite a lot of running back and forth, and it sometimes takes me longer than it should. If I’m lucky someone at the dock will see I need help and catch my lines for me.