To give you an example (may apply to some or not to others) I am a beginner-intermediate sailor. I've had my own sailboat (32 feet) for three years now, and had instruction on and off again for a couple of years before that.
I recently did a 50 nautical mile solo coastal trip with near gale conditions in two meter seas. It was all I could handle and exactly what I wanted to handle at the time. But I couldn't have done it without hurting myself or my boat a year ago.
Whats helped me is going out for day sails
regularly, gradually going out in more challenging conditions. Start out in very mild conditions where there is barely enough wind
(less that 10 knots) to get going in flat seas. There is much more time to react and figure out what to do safely. Then gradually go out in choppier conditions or with higher wind
gusts to practice practical things like reefing down and avoiding uncontrolled jibes, roundups or breeches. You might find you have no time to think and react if you have not had the prior practice in easier conditions. An autopilot
helps, but also requires practice and understanding how your autopilot
works in various conditions.
Another thing that took time was finding out what kind of condition my boat was in. You can't count on a boat you buy being sea worthy even with a pre-purchase survey
. It takes a lot of familiarity with the boat to know where the skeletons are buried. Mine was not that bad, but it took patience to uncover the systems that needed improvement and money
to do the improvement even what I was able to do myself. There is still much to do to make my boat 'cruise ready.'
For me night sailing, overnight sailing is the next step, but I'll probably get my instructor to do the first one with me.
Hope my beginner's stories help get you ready for your trip.