Hawaii trip?

If it were me, I wouldn't do it unless you had the money to extend the trip for a longer period and the time to do so.

My FIL owns a timeshare on Maui. We have never gone even though it's free to stay, because of the cost to fly there and the fact that we'd want more time than a week if we were to go that far away.
 
I'm going to be the lone dissenting voice here just so the OP doesn't feel silly for even considering this in the first place. DH and I had a wonderful 4-day trip to Honolulu for our anniversary 2 years ago. We stayed right on Wikiki Beach, had a rental car and did every major tourist thing going in the time we had. What we didn't do is spend any time just laying around on the sand or in our suite - we could relax at home for free!

The reason we chose to do this was that we REALLY wanted to see Hawaii on the time and budget we had available and FWIW, I don't think the OP is truly motivated enough to make it worthwhile for her family. 4 days going "flat out" at everything that interested us cost about $6,000.00 including airfare (and the long flight and time-change were brutal). But we came home loving each other and the experience and don't regret one thing about it. Based on what's been said, I would not recommend anybody do the same if they were just going to end up feeling unfulfilled and like they'd wasted their money.
 
There are alot of condo rentals on the island that you could do to add more time. I would probably do Oahu and then fly to Maui and rent a condo for a week.
 
We went to Hawaii once, and my husband refuses to ever go back. He hated the long flight and the cost of everything and even the other annoying tourists that were there. He just really didn't find anything he liked well enough to want to go back, at all. He says he'll go somewhere in the Carribean or Mexico for way less money. We've done the Disney cruise which he loved, Mexico all-inclusives, which he also loved, and, of course, Disney trips. And Wash DC which he loved too. Hawaii has been the only place we visited that he does not to ever return to. I wouldn't mind going back, but have to agree that I didn't love it enough to justify the cost over other types of vacations we've taken. I agree, 4 days is not a lot when you consider the time you are taking to travel to get there and time change (unless you are already on the West coast). I personally would not bother going for less than 7 days.
 

Yes, hawaii is worth the money. I would even consider going the 4 nights on Oahu if that was all I could afford, but if you can stay longer and hop to Maui it would be even better. Not sure why you put vacation in quotation marks, Hawaii is a completely reasonable vacation spot? I live in the Midwest and at least 2 hours drive from the closest major airport, so the flights and travel time are extremely long for me as well, but Hawaii is my top pick for vacation (I just got back from a trip a week ago). I honestly don't think you need more than 4 nights on oahu though, but I'm not really into the tourist attractions anyway, I prefer water sports, beaches, easy hikes, and nature activities.
 
4 nights would be a tease. Airfare is very expensive from the east coast. Hawaii in general is expensive. That being said Hawaii is a must do at some point in your life. We've been twice and are now talking about moving there. In the words of my then 10 year old "Now this is what I call paradise". We spent 9 days on Oahu then took the NCL cruise which took us to 3 additional islands. The whole trip was magical.
 
In the past, I have priced airfare cheaper by separating the trip- pricing airfare from my home to LA and then separately pricing airfare from LA to Hawaii.

Very good idea! We used SW points to get us to LAX and spent a couple of days in SoCal. Then we used BA points for the flight to Hawaii.

Hawaii is worth every penny but only if you have the pennies. I would accept the prize, add additional nights, and go if you can afford it.
 












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