Reducing our Hawaii trip costs

We debated quite extensively if we wanted to stick to our plan of taking the kids to Hawaii for Thanksgiving. We actually made a long list of places everyone in the family wants to visit - it was quite hilarious to see some of the nominations. Nick desperately wants to go to a dude ranch in Montana, for example. ;-) In the end, we decided that by flexing the dates a bit and having the boys miss a couple of days of school, we could make it work. That said, it's really fun to have a list of places we all want to go - we will definitely be opting for some weekend trips in the next few years.

Our original goal was to pay for the entire trip with points (airline & hotel). It quickly became clear when planning that it wouldn't work that way, and we'd be paying a huge premium for using our desired days.

Here's what we ended up doing:

• After a bit of research, the most optimal winner would be to leave the day before Thanksgiving (11/23) & return 11/30. This would mean only a few missed days of school, but would make the tail end of the trip non-peak days for both the flights & the hotel.
• I spent time on the phone with Starwood (my hotel points are through them, via our credit card) & was able to use points for 5 of the 7 nights. The agent actually suggested the best way to redeem the points to maximize both the cash outlay & points required. This required about five years worth of points. Can't remember exactly, but that's my estimate. 
• We will pay cash for the remaining two nights, totaling $1111.70. Yes, it's crazy. This is for a one bedroom villa (i.e. a condo that has a separated room for our sleeping vs the kids). We could have gone for the studio one bedroom, but it doesn't have any separation between sleeping rooms, and we all find it tough to sleep in that scenario. The two days we are paying cash for also include breakfast for free, so that will save a bit & be a nice splurge. 
• We will make (almost) all of our meals. Last time we went out on Thanksgiving, and while it was fun, it was also around $200, which is the cost of the majority of our groceries for the week. This time I think we will barbecue a turkey breast & make some fun sides.  
• As for the airfare, we didn't have enough points to pay outright for all four of the tickets, so we explored other options. We ended up using a companion fare ticket ($99 + tax) for one of the tickets, and paying for the others with cash. However, because we were paying with cash, we were also able to use my free first class upgrades. I have six, so we will all be in first class on the way back, and two people are guaranteed first class on the way there. I'm also on the standby upgrade list, but it looks unlikely. So, we also won't need to buy food/drinks for the flight home, and it should be a relaxing return to reality.
• We also used the airline points to pay for our tickets at Christmas, saving about $1200. This will help to offset the Hawaii flights. Total for the Hawaii flights = $1760.

Total spent so far for 7 nights in a one bedroom villa, and (mostly) first class flights = $2870. We still need to book the rental car, and of course will have to pay for food (the difference between our normal grocery bill & the vacation food), as well as any meals out and activities. The goal is to limit the remaining expenses to $1200, which should be totally doable.

And, that's it! I love planning our trips! One of the deciding factors on taking this flight now vs later is that I have premium air status that will be ending at the end of the year. This means I have the first class upgrades, get 8 free checked bags for our party, etc. We will also fly home from Christmas on the very last day of 2016, for the same reason. Thinking ahead. ;-)

What about you? Talk to me about how you use reward points on airlines & hotels!