re: USVI or Maui for 9 days?

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9/23 - 10/1

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Those dates are prime hurricane season for a St. John trip. The island will also be dead. Most restaurants & businesses close at some point starting in August until early November. Some are only closed for a week or two, but some close for a couple of months because business is dead. On the plus side, your rental could be the cheaper than other times of the year.

It doesn't seem that travel time & the cost of a Maui trip are much of a factor for you for this trip. My suggestion is to absolutely visit both eventually, but go Maui (Wailea) this time. The next time you want to take a similar trip Maui might be more prohibitive. Plus, late September isn't a good time to visit St. John.