US/BVI Experience
I have chartered three times in the USVI & BVI, for a total of 5 weeks time. The last time was 15-days on a Moorings (Beneteau) 402CC with the Moorings out of Tortola. We cruised mostly the BVI that time, with a little time spent on St. John and St. Thomas. My comments will be related to cruising the BVI or USVI.Generally, it's a GREAT place to get your feet under you, before jumping off into the wide-blue. Drake channel is well protected, with few hidden hazards. There are a few, but they are well known. The distance between good anchorages is short.Weather, general: June can be nice. Not terribly hot. July can be kinda hot for sleeping. Breezy anchorages and wind-scoops are a must. A windless hot/stuffy marina in just about insufferable. August is more of the same. This is the low season for more than just storm-danger. In June - Aug the trades are typically honking from the ENE at 15-20 knots, so it's perfect for sailing fast. One day we sailed from V. Gorda to Anagada with the knot-meter pegged at 7 knots or more the whole time. Schweet.Weather, storms: Periodic lows / depressions of note sweep the islands during this time, typically originating from the East, but not that often. Perhaps once every 1-2 weeks. They are fairly predictable, but move alot faster than you would think. Listen to the weather report religiously every night (8pm I think) and plot the LOW's positions and predict their locations for the next day. I almost came to grief thinking I had 6 hours to skip to the next bar, er anchorage, when one bore down on me while leaving Sopers Hole (Tortola). The wind can jump to 40-knots and temperature drop 20-degrees in a flash. It's good to have heavy ground tackle and put out two anchors in this situation. Alternately, pay the $20 for a mooring. You get to see who knows how to anchor properly when one of these comes through. I almost ALWAYS dive the anchor and set-it by hand, but then I'm blessed with being able to hold my breath long enough to free-dive to 35-feet. It's handy. Typically I try to anchor in 15-20 feet of water to keep the scope/swing-radius down. The hills are tall, so watch for the wind-backing after passing over the tops and actually blowing you TOWARDS the 'windward' beach. It's whacky. I typically try to find a low-spot to anchor near so the wind behaves itself. There are nice spots on Cooper Island and J.V.D. for this. Get there early (by 2-3pm) or all the good spots will be taken. The off season is not too 'off'!Watch out for anchorages where the sand drops off fast to way-too-deep. The Bight (Norman Island) is notorious, but there are many moorings there. It's wise to use one. There are many other iffy spots like this. There are excellent cruising guides that cover all of this.If the weather is going to be REALLY BAD. I.E. Hurricane, Hurricane Hole on the south coast of St. John is the ticket. YOu can tie-up to stout trees, and the protection is exquisite. I have not had to do this, but have read about it.As far as getting to FLA from BVI, good luck. I'd love to do this, but have not tried it. It's 1000 miles of down-wind, so how hard could it be?

I'd suggest you consider sailing more than 7 hours a day if you are going to make it in a reasonable length of time. I'd also suggest finding good charts and a couple of good cruising guides and planning it out step-by-step with contingency stop-overs, and back-up plans. Sounds like an adventure!