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If your going to be chartering for a week or so... then you should still be able to do a BVI trip but have the charter company agree to move the charter dates if "weather problems" appear to be imminent. If you truly have an open time frame that can be moved at last minute then go for it. Cost is far cheaper in this Off Season for the West Indies. It will be a bit hotter with less winds but generally calmer seas unless you have a storm coming down on you.
Note that some places will be close for vacation/ repairs in Aug/ Sept / Oct but generally only a month each location and few of the major spots close entirely.
Always keep a Weather Eye and have your lap top set up for the important weather, wave and wind forecast sites.
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I prefer a sailboat to a motorboat, and it is my belief that boat sailing is a finer, more difficult, and sturdier art than running a motor.... Jack London
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