I will be going next summer. We want to do the non-stop fly to flight to Maui. Does anyone have experience is being able to get 4 tickets via miles? Should I book departure flight the day it opens and the return flight once it opens? Any secrets would be greatly appreciated. We have some miles in our accounts but not enough for a flight. I was planning on transferring miles as well from starwood. Is it best to transfer to one account and book all the flights from one account? I'm familiar with Hawaiian airlines but this is the first time booking on points with Alaskan Airlines
The cheapest way for you would be to transfer the Starwood points to British Airways and use those for a flight on Alaska, as they are partners. Since British Airways is distance-based, and a non-stop from the bay area to Hawaii is between 2,000 and 3,000 miles, it would only cost you 25,000 British Airways miles round-trip, which is significantly less than using Alaska, Delta, or American miles for the flights. Because of the bonus of transferring points from Starwood, this would be equivalent to 20,000 Starwood points per round-trip ticket.
Since Alaska flights aren't bookable on British Airways' website, you would have to call, but you should be able to convince the agent to waive the phone booking fee since it's not possible to book Alaska awards online.
For checking availability, the best way is to use the aa.com site, and search for 4 seats using miles. Any non-stop AS flight in the results will be bookable with British Airways. If you are flexible with the return date, I would book each one-way separately, but if you are not flexible on the return date, wait until your return date is available and book it together as a round-trip.