I first find out which boats on my wish list is available. I then check into airfares and see if enough seats are available for all crew members. Once I find these available I put a hold on the boat I want for one week. Once that is confirmed, every crew member buys their air travel within one hour of each other. We don't put much stock in the best time to buy air travel. We either like or don't like the price upon checking. We've given up on getting everyone into Beef Island at the same time. We now fly into STT for nearly half the price and still arrive in Roadtown no later than if we flew into Tortola. Have a great time.