Hi blynch12:

Although I am not an expert on this general route, I am somewhat familiar with traveling from the Southwest via SFO to Hawaii (Ohau mostly...never visited the "Big Island").

I am a frequent flyer with United so I usually fly their system. I called them (1k desk) for a quote of lowest round trip (RT) economy fare departing BOS on Nov 2 and returning Nov 11. The routing I was first given by the 1k RA was BOS-Chicago (ORD)-OGG (Maui) -then a connection with Aloha Airlines to your preferred destination. The quoted total price, including taxes, fuel, etc., was just over $1000 ("all-in"). I then asked for RT routing through SFO with a stop for about 48 hrs on the return leg of the trip in SFO and the out-bound routing became BOS-SFO-HNL(Honolulu)-followed by inter-island hop to the big island. (The recommended return route was the same itinerary.) The fare went up about $50 for this now single stopover itinerary. Note that if you make two stopovers of more than 24 hrs during your entire trip the fare becomes outrageous.

Stated another way, you can usually make a stay of no more than 23 hrs. on most fare classes along your routing multiple times but only one stopover of more than 24 hrs. for no additional charge on most classes of inexpensive tickets but rules may vary from airline to airline. Of course, the schedules must be such that flights and seats are available for any stop/stopover.

I use the one-stop allowed rule often in SFO as I like the city and I usually transit it several times a year on international flights to the Far East but also Hawaii as I just did this past week (I stopped on the return portion of the trip). I have never used the "23 hr." delay strategy as it is not so important to me.

I recommend you seek the advise of folks on this board, as you are doing, and also speak with a travel agent or airline customer service person regarding your proposed trip. If you do not have a favorite airline, I would go to a web site, eg. expedia or orbitz or etc. and compare losest fares and then call the airline and ask reservations about restrictions on stopovers, delays, itineraries, costs, etc.

If you need more assistance send me a PM and I will try to help.

Good luck.