You are ready when you have done all of your home work; Study the charts, look for hazards, study the anchorage, enter way points into your GPS, know your waters like the back of your hand, watch and learn the weather patterns in your area; the list goes on and on. Than once you have done your homework, you have to display your knowledge to your partner. She has to become comfortable with your knowledge and experience. Once you have demonstrated to her your vast knowledge, simply by doing, hopefully she has the same passion as you do and will be willing to make the sail. Some significant others never develop that same passion. Try as hard as we will and it makes no difference.
I would be one of those that would at least spend one night on the island. Once you get there you are going to want to enjoy it and not turn around and head right back. Relax and take the time. Call in sick one day if you have to. Maybe wait till January when the Holiday is over. I guess working retail this must be your busiest time of the year. The island will still be there.
For me, it was the Lake was calling me and I answered the call. You seem to have that same call. It's in your blood.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White