Bigbeam,
Convince her? You may be able to wear her down and get intellectual concession, but you stupid man, that''s not what you want.
<em><b>Happy wife, happy life.</b></em>
Put this at the top of your list of goals, or you are doomed to failure. "If push comes to shove, she would do it" sends up huge red flags-- are you willing to shove? What will be the price you pay for that?
Typically, women are more security-oriented than men. It seems as this may be of central importance to your wife. Assuming that is the real issue, you need to make this your project. Her attitude needs to become more positive about this before you can even think about getting what you want: a Carribean cruise <em>and</em> an intact marriage. That means you need to lay a pathway of secure stepping stones for her to travel from where she is to St. Kitts.
If I were in your foulies, here''s what I would do:
<ol>
<li>Relocate closer to the shore.</li>
<li>Keep an affordable boat for weekending.</li>
<li>Be completely safety-conscious when sailing with your family. Teach the boy to be a good sailor: seeing him as self-reliant instead of her helpless baby will help relieve her fears for his safety.</li>
<li>Be a good mate: don''t dominate, yell, or isolate her from what''s happening. Include her in the operation of the boat, including decision-making, equal to her skills/comfort zone. Praise her regularly and sincerely. Let her become invested.</li>
<li>Constantly listen to her & show empathy, understanding, and support. Forget the Carribean exists, or she may think you''re manipulating her. Your goal is to create positive family memories, which will have value on their own.</li>
<li>After a seaon or two, mention the possibility of some short-committment summer coastal cruises when the boy is out of school. Gauge her resopnse to this idea. Be content to become a life-long daysailor at this point.</li>
<li>If you see that necessary changes in her, float the idea of the big cruise. Give her reasons to believe she will have regular contact with family/loved ones while on the cruise, and that she will be financially secure once she returns to shore life. Will she be torn away from every relationship that is important to her for two years? Will she have a house to come home to?</li>
</ol>
I just don''t see you jumping from your situation to the cruise in one step. You ain''t going cruising (well, with her, that is) until her perspective changes.