Obvious stuff, but reminders are always helpful... (This assumes you've already mastered how to sail your boat.)
Find a place that she'll like that's a short sail away. Take her there and back a few times. Maybe a great place to have lunch. Make the whole trip wonderful -- good food, no dishes to wash, the music she likes, a smell she likes, a shoreside activity she likes (shopping, bowling, horseback riding, shell collecting, whatever it is), good metrics on your progress there and back, a fun onboard task for her (steering, buoy spotting, sail trim, whatever she likes). You are playing host to a new guest aboard, one that you highly value.
Second, avoid the downside - no bad weather, no big waves, no excessive heat, no rain, no breakdowns, no boat clutter, no head smells (air out the boat before she gets there), no dirty anything... you get the idea. You sail with many safety Plan Bs in your mind. Have a plan B if a dating downside surfaces - ferry ride home, rental car, hotel stay, friend to call, etc.
Third, add a fun custom, like taking a picture of you both at each destination, kisses after every tack, foot massage (for her) after every gybe, finding a rock to write on, sending yourself a postcard, putting a mesage in a bottle, toasting the sunset, silly laugh contest, whatever. At a minimum, kisses at sunset.
Enjoy the smile on your face.
Repeat until she brings up the idea of going to Catalina Island.
(If she doesn't bring up Catalina Island after 10 trips, show her a picture of something interesting on Catalina Island and talk about what makes it interesting. Repeat after every 10 trips.)
Great minds discuss ideas;
Average minds discuss events;
Small minds discuss people.
The best minds discuss sailing (and a little bit of politics). I don't know why. It's a mystery!
Last edited by Bene505; 12-08-2011 at 10:41 AM.