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Here is the other thing. She has asked me if I thing its going to be big enough? Is it too small? I told her is the maintenance and overall cost is a lot better on a 30 foot boat. But I screwed up and Chartered the 36 I down in the BVI this past spring. She thinks that boat was much better in size...
Well, I sail a 30-footer, but only liveaboard for the duration of each cruise... When I'm alone, she suits me fine... But when I have company, things can get very tight, very quickly... :)

Only you can answer that question, of course - some couples seem to manage just fine on a boat of that size. But in my observation, they are a bit of a rarity out there today, and most more 'mature' couples are on boats considerably larger, at least closer to the mid-30's or so...

I STRONGLY suggest you try an extended shakedown aboard your present boat before making a final decision, or proceeding much further... Trust me, if the size of the boat is likely to be an issue, it won't take long for that problem to surface... :)

Stuff like a Honda generator will occupy a surprising amount of your storage space on such a boat. Mock up a cardboard box the size of a Honda 2000 (which everyone seems to think is essential these days) and stick it somewhere. Sorry, but you're gonna have to ditch some of those sails. A second mainsail, and that 155 genoa, is gonna eat up much of your precious storage space, as well. That alone is one of the best arguments for headsail furling on a cruising boat of that size. Whenever I remove my sails and stow them below, the space in which to LIVE on board is reduced dramatically...

Other things on your list strike me as perhaps a bit superfluous... I'm a huge proponent of windvanes, for example - but why do you feel you'd need one for "harbor hopping" down the coast, and thru the Bahamas to the Islands? Put your money into a good AP, that alone should be more than sufficient for such a trip...

But seriously, the size issue is the one you must address first, that's likely to be the one that makes, or breaks, such an endeavor...
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