Ok I made up the part about Free Beer but figured nobody wanted to see another "ferry question"

Last year we let the Moorings take care of our ferry & taxi reservations and this year it is my turn to plan our trip.
I was told for the six of us that I could have the Moorings book the ferry/taxi for $100 per person roundtrip. First week of June we land in St. Thomas at 1:40 (we hope) and I have already contacted Kevin (Thank y'all for the tip on him). I'm not sure if landing at that time makes a difference on if we should leave from C.A. or Red Hook for the fastest departure? Guess the question is would y'all just take the easy route and let them handle our reservations or should I book the ferry and grab a taxi when we arrive in road town.

Thanks a bunch!