Been there and done that with crews of eight or more. We usually charter at least two planes. Three on many trips. The other very common option is two go ahead of the rest of the gang and pick the boat up meeting the rest of the crew near STT. I always find getting the boat away from the dock better with 2-3 people and the same on the return. In general with a little effort you can find a boat for ten days for the same price as the 7 day week. Use those "free days" to pick the boat up and return the boat with seven days or so of party in the middle. For us the idea the entire group must always be together for the entire charter gets old. We also do our best to never make any of the "vacation" a planned race from moment to moment.... must do, to must do. We never move the boat anymore until everyone is ready. Only then do we decide where the boat will stop next.