How are you getting to Tortola? How are you getting to the charter base? You will find the cab drivers don't like dogs. The airport personnel likely will not be helpful either. Does your charter company know your bringing a dog on board? They likely won't like it either. Everything will take more time. Private cabs, more time at customs at the airport. More time at the airport terminal allow time for long delays on both ends.
By the way I love dogs and I would not dream of doing this. I would not put myself through it or the dog.
