Next summer (2016) I am planning on taking my family of four, along with my sister in law and her two kids, and my father in law, on their first bareboat adventure. Though I've chartered in the BVI at least 5 times, I've always been crew. As such, I have a number of questions.

First, any tips on making this more cost effective? It seems that it's cheapest for our flights from Pittsburgh to fly to SJU and then into EIS rather than what we've traditionally done, which is fly into STT and then take the ferry. Any tips though on how to make this less expensive would be great. We're looking at about $650 PP now.

Second, I'm not sure I'll qualify to captain the boat, even though I've crewed a number of times and have sailing experience, I'd almost rather not have the stress. So, if we hire a captain, what is appropriate for a tip?

In terms of chartering boats, who do you recommend? I have gone through the Moorings several times, but interested in less expensive options if they exist. Right now I'm primarily looking at a Moorings 4000, 4 cabin cat. With a captain, however, this looks to run about $9000.

Any other suggestions would be great!