Just got back from my first Regatta. Wow. That's all I can say. Wow. I plan to go every year till I can't raise a halyard anymore. I've already got vacation for it next year. 10/13-22 2015.
We got a Moorings 4600, 4 heads/4 cabins. Split it 8 ways. Whatever you decide on, charter company, cat/monohull and size (heads/cabins) just make sure you're comfortable with the amount of people vs. space vs. $ per person.
My buddy skippered but I've got 104 plus own a 30'er down on the Chesapeake and would feel comfortable doing it myself next year. They are really helpful at the Moorings, they'll give you a thorough briefing on day 1 and I believe even give you a skipper for the first 1/2 day at no extra charge to make sure you are comfortable. Either way, like madjack said, it's pretty easy down there. Lotta deep water, mooring balls, etc. Too much wind or not enough? Just motor. You're not payin for the gas.
I wouldn't worry about the provisioning package unless you are crunched for time or don't wanna deal with it. Better to make a run to the grocery store or better yet put in an order and have them deliver it. There are tons of sample provisioning lists for week long charters floating around the internet. You can always re-supply with the basics - water/bread/ice/beer/produce at little shops at MOST islands....not all.
Booze, just buy it at Road Town or Sopers Hole before you leave, no biggie. Remember. First thing we always run out of? BEER. Throw in a case every day to keep it cold and keep the rest stored somewhere.
There were a buncha non-revs, more than normal I'd say, heading down to STT but there are a bunch of options so between different airlines, Cape Air, etc I didn't really have a problem. You can always buy tickets on Cape Air from Beef Island (Tortola) to SJU if you're worried. Get to SJU and you're home free. I did STT and a ferry on both ends from Road Town. Plenty of service to STT plus you can be in the jump (domestic).
All in all, it's a hell of a good time with some great folks. Bring more advil than condoms.
PM me if you wanna know anything else.
