Planning Grand Cayman to Westend, Bahamas

[FranklinGray]

I am in Grand Cayman now and need to get to the Bahamas (yeah...I know what season it is). I like my weather window for leaving here Wednesday morning. Looks like a 2 day sail or motor-sail west around west end of Cuba and then a 2.5 day motor into light winds going east before turning it north when the wind picks up. All looks good on paper huh? Things never go that smooth so I have some questions as I've never sailed this route before:

1) How much problems do you think I will have if I try to cut into territorial waters, especially around the west side of Cuba (I am planning on using that inter-territorial channel on the west side)?

2) With how the winds are foretasted, I'd like to stick to the north coast of Cuba when motoring east but hear there is a westward current which I don't want to be in. Thoughts on that besides me missing out on the easterly current?

3) My biggest fear, being in the easterly current with a wind on the nose causing slow progress and steep waves. How strong does the wind have to be from the east to cause nasty waves in the stream above Cuba? Some tell me it isn't like the east side of Florida with a north wind but I'm not so sure they are speaking from experience. Anytime I'm in a current and the wind is against it, it always seems uncomfortable at the least.

4) Should I be able to pick up the VHF weather stations north of Cuba or will I need to be more on the Key's side to pick them up? A little worrisome making a plan on going through the stream on a 2 day old weather report during a hurricane season although it is expected to be mild season.

5) Any other thoughts on this route?

Note: I will not break this leg up into smaller ones unless while at sea things get really bad. Personal reasons unrelated to normal passage making.

[FranklinGray]

I take that back. Do not plan on running the northern coast of Cuba due to the counter current that is predicted via the following website. Not sure how accurate it is, but if my planning is right and the help of nothing going wrong, then I should be motoring east in the easterly current into 10 knots true wind and two foot seas.

I guess I'll go with that plan and if I have to, drop into the Hawks channel if it gets bad or the keys if I get a bad weather report on the VHF.

So what is the farthest you've gotten weather on the VHF south of the Florida Keys? I guess that is my biggest concern now.