I would second or third the Bahamas recommendation for the time frame, but since the OP says they really want to see the BVI...
We did this trip several years back, from Lauderdale in December down to San Juan
, then over to the VI and that general end of the Caribbean
, then back up in May. The trip over was earlier in the season than you are estimating, the return probably about the same.
For the trip over I think we took 8 days from Nassua to San Juan
. Close hauled and lumpy the whole way. Not terrible, but not the most pleasant sailing. Whenever the wind
comes north of east use it to make a little extra easting. That way when it comes back around more easterly you can fall off a little bit. From San Juan it's upwind to the VI, but not that far and you can pretty much daysail it.
The trip back was a sleigh ride. Quite a blast. If I were having someone deliver one way I would probably have them deliver to the islands, then bring the boat back. You can make your way back through the Turks and Caicos
, then the Keys (bypassing Miami) then on up to the panhandle. Off the wind
, and with the current
I would hope your Mahe could do 150 mile days on a pretty regular basis. That should give you about a 3 week return with a little bit of leisure time on the way.
Which leaves you with two months in the islands if you get the boat delivered that direction. The question I would ask is whether you want to do passagemaking as part of the vacation
, or if you do it just as a necessity? If it is a necessity then consider either delivery
both ways, or just doing the Bahamas. Personally, I love passages. Nothing quite like a week or so with nothing but the boat and the ocean. Different strokes...
BTW, my parents started me down this road when I was a kid. Has led to a pretty interesting life (at least as far as I am concerned) although I don't fit in to "civilization" too well. Can't think of a better way to teach some responsibility and real-world smarts. Would strongly recommend you involve the boys in running the boat as much as possible (some of that will depend on their interest level). I started standing watches on my own at about 9, progressed to night watches on my own at about 13. Your kids may battle it from time to time (I sure did), but my perspective looking back is pretty darned positive.