When you make the choice to go cruising, the next question is when. This question can seem like a very difficult one to answer, as there never seems to be a correct answer.
When you leave, you need to say goodbye to your friends and neighbors, your job, everything that happens right there. Then you need to pick a weather window to go, which can make it seem even harder! Last, you will want to get prepared to go cruising that way you don't get caught off guard.
This will lead to a lot of thought and considerations as to when the right time is to go. If you plan too far out, how will you know the weather? If you don't plan, how will you finish things up with work?
This can seem like a really daunting task, and people will continuously ask you "when are you leaving?"
The best way we have found to decide when to go is to choose an arbitrary date. We pick a date and stick to it. When that date rolls around, we cast off, weather dependent. The weather can be finicky, and we try to avoid bad weather. We also know that the weather will change, so leaving in perfect weather means that you will hit bad weather the next time it changes. Based on this logic, we will cast off if it is not a storm and not raining. Light winds, or medium winds are welcomed as we leave the marina and head to new shores.
We also don't fret the arrival of the departure date, as it means to us that we are casting off now, not that all preparations need to be finished.
You will never be ready to go, and if you don't take a blind leap off the pier into the cruising world, then you will spend your entire life getting ready for the world you never explored.