If you want the Admiral to share your new passion with you, it better be fun all around. Very few like to sail for 10+ hrs in one day. I have and will do it, but only when necessary.
I think that out one day, dinner, then back the next sounds much better.
You can manage your trip out more easily than back. "every take off is optional, every landing is mandatory". If the weather/seas/wind turn once you are there, you may either need flexibility to stay or could subject passengers to a ride they don't enjoy. Then, I assure you, they won't be back. Ironically, the better weather you wait for, the more likely you will motor.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.