Heading to Oahu and maybe Maui 2014
Hello all, Anyone want to give a total flyertalk noob some advise? My wife and I have been talking about visiting Hawaii for what seems like forever so we finally decided we're going to commit and make it happen. What recently pushed us to take the plunge is some reletaves of ours are moving near waikiki due to work for the next two years. They already insist that we come visit and stay with them for free while we're out there. I figured why not island hop to Maui since we'll be out there anyway.
My goal is to fly myself, my wife and my 10yr old son to HNL from PIT for 7 days then to an undecided Maui condo/hotel for another 3 days then back to PIT as inexpensively as possible. I'm willing to spend a bit to stay in Maui if need be. We can travel any time between March through July of 2014.
So here is where I mostly need my guidance. I currently have 0 points for anything but I just signed up for and got approved for the 2x 35,000 Hawaiian Airlines miles. My wife will do the same after we meet the spending requirements for mine. Giving us ~140,000 by the time we should be booking the flights. I'm not sure what other points I should go for. We looked around and it seems like the only flights to get to hawaii from PIT would be through connections on Delta, United or American Airlines or we could go to JFK and use our Hawaiian points for a direct flight from there.
Sorry for the walls of text but any beginner guidance would be appreciated. Also, thanks in advanced for all of the awesome info that's already available from fellow flyertalkers.