As others have mentioned, the food budget is far too low. Moorings are $30 a night, anchoring is free. The wind will blow from an easterly direction. The tide will be less than a foot. The BVI Spring Regatta is April 4-6 and there will be more than 100 boats racing in the Sir Francis Drake Channel during that time frame. I've been racing there for 8 years and always sail the BVI the following week. More often than not we have encountered 20kt winds and 5-8' seas most days if venturing out of the protected waters in the channel. Your itinerary is the standard counter clockwise trip around Tortola that most first time visitors follow and there's nothing wrong with that. The boat will sail fine. None of your destinations are that far apart. If you want to race, come crew on a race boat. If you're in the BVI to enjoy steady wind and warm water while on vacation, chill and go with the Ilon flow mon... Stay the hell out of the way if you are on a charter boat during the races, pretty please!!!