Expand your library
In a very big effort here in not trying to be offensive, it sounds like, from your questions, that you may perhaps not have as much blue water experience as maybe some other folks do, so let me make a suggestion. Go to your local bookstore and purchase yourself a copy of the very, very fine basic sailing text entitled, "Royce's Sailing Illustrated," from Running Press in Philadelphia, PA, ISBN #0-89471-696-4 and give it a thorough reading. It contains all the answers to the questions you asked, complete with illustrations on how to rig some of the components about which you asked. It's also chock-full of very useful sailing info and, actually, it was the first sailing text I ever used back in the yacht club sailing program days of 1967-68 when I learned how to sail. I still use it today and have several copies and often give copies to friends when they ask me to teach them to sail. It's not expensive; only about $12 and you will find it very useful. Buy 2 copies and keep one on board.Secondly, that crossing over to Bermuda can be pretty tricky, so talk to some people who have actually made it. I haven't, so I can't help you much other than to say I've read alot about it and it takes pretty good seamanship. You are your own best judge of your sailing abilities so please be pragmatic and objective. You've got a good boat that is certainly capable of making the trip so the biggest question is whether your skills are up to snuff.Jeff is right about hurricane season, but let me toss in that most storms are late summer storms -- altho anything is possible. Watch the weather in Africa; if it's raining lots in Africa when you are talking about starting your trip, be particularly attentive to weather reports. Lots of rain coming off the West Africa cost can churn up into some pretty nasty storms. If you don't have weatherfax, get it and pay attention to it. If you don't have it, or can't afford it, stay in port because the Atlantic is a nasty place to be in a big blow. On the flip side, there are a lot of safe harbors during a storm in the Virgins and I have been down there during Hurricane Season and dodged a few bullets. On the other hand, if a Big One is coming your way, head to Venezuala -- go south as fast as you can or tie up your boat, make sure the insurance is paid and fly out of there. Hope I didn't insult you. Good luck.