So before I offer my thoughts, let me ask, what inspired you to have such a dream? The heart of your passion for this dream will be in that inspiration. I think it is important to think about, not to discourage you but to encourage you. There will certainly be freedom and adventure... but ultimately you are not talking about just sailing, you are talking about the sea, a boat and calling both your home. I wouldn't worry about certifications. Later on maybe, I don't know. I have sailed quite a bit and never been certified for anything. Here it is: Get a really fun and fast little boat. Like a Laser or a Hobie Cat. One for each of you. Then take them out and make them go fast for fun. Race each other! You will likely catch the bug for sailing and for all the little tricks to make the boat go with nothing but a big piece of cloth and a breeze. If you catch that bug you will become skilled out of your love for the sport not so much from any lessons you think you may need. Then you will start to look at all boats from the standpoint of how much fun they can be. As your love for sailing grows, your imagination for what you can do with these skills on the open sea will guide your choices as far as lessons or certifications you may need and the kind of boat that suits you. If you love the sea and you love to sail, it will work out beautifully. And you will have some great tales to tell... Give a shout when you pass by the Channel Islands, I'll come out and race you for a stretch!