Consider a simple rig where all the pieces can be stored inside your hull. Keep it there, even on non-sailing days. If the weather changes you can pull off the water and rig your sail in a minute or two. Make your rig strong because the winds will always be stronger. Make certain you can always drop your sail in an instant, because big winds come fast.
Practice self rescue. Very few people can roll a boat with a sail. More often a paddle float or cowboy rescue is involved. Less often sailors lower their rig the reenter and roll. I often leave the sail up and use its pull to help balance my boat as I enter from the windward side. Make certain you practice rescue procedures on calm days with friends at hand. Will the radio or knife catch on your boat as you try to pull yourself aboard? Will the sheet or the other lines be likely to ensnare you? How long can you hold your breath and work underwater? If you have friends practicing assisted rescue, please be mindful of your hands, never ever get your hands between the boats. In windy weather the chop will smash your hands and make for a long day towing your friend to the Hospital. Sailing is extreme kayaking and you will capsize.
When I first started kayaking it took me about a year to figure out how to get in and out of the boat at the steep slippery launches I used without capsizing, but I never capsized while paddling. As I became a better paddler I practiced capsizing, but I still never turned over in the ocean or even in the little bit of white water I paddled. Lately I started paddling in the surf and I capsize at least twice every time I go surfing. While sailing is not as likely to spill you over as surfing I promise that you’ll benefit from planning to swim a lot in the beginning. Planning for swimming and recues will give you the confidence to push your skills and try new things that will make your boat go faster.
A sail can add safety to any cruise. It makes it easier to tow in difficult conditions. It could allow you to continue travelling if you become injured. A bright colored sail is far more visible than any kayak at a distance. A kayak sail adds initial stability to any rig. For long cruises the added rest and easy miles will help you save your strength for days when it is really rough. It seems to me that when I have a sail it becomes very easy to do longer days. When I do not have the sail I really start to suffer a little at about the 22 mile mark.
Yesterday I did not get to sail, but the rain brought the water up in the river, so I got to practice playing in some current. I’ve got my first race ever on Easter weekend.