Old Jul 24, 18, 9:12 pm
  #15  
sweetsleep
 
Join Date: Sep 2014
Location: Nashville,TN
Programs: AA Gold Elite
Posts: 354
Maui is aspirational for people world wide and with good reason. Be very glad you have a hotel nailed down in your pocket already.
Have you considered using miles outbound in economy for the daytime flight and using Biz or First for the awful red eye back to the mainland? Been there, done that and I would prioritize premium cabins for the flight back to the mainland if you do not have enough miles or do not want to use a ton of miles in premium class.

Also, if you choose to fly in a premium cabin from Maui, whether on miles or a paid ticket, GET TO THE AIRPORT EARLY!! The last time I flew back on miles from OGG my sister complained about how early we arrived. There was a couple that arrived shortly after we did that were bumped out of First/Business even though they had confirmed seats. We heard the wife berate her poor husband for 2 hours. Yikes. Sister stopped berating me soon thereafter. Nuff said.
If you get a rental car, the gas lines at Costco(very close to the airport) are LOOOONG. Might be worth paying a bit more for gas elsewhere but I suspect all gas stations will be crowded regardless-factor that into your timing for arrival. I suggest that one of you drop off baby, a spouse and luggage(remember all bags need an agricultural inspection which can add time to checkin) and then the other spouse head to get gas and return the rental car(and the shuttle back from the rental car office to the airport incurs additional time).
Hope this helps with your trip plans.
Maui is really beautiful and worth the effort to get there and back. Do not even get me started on how expensive food is. OMG
sweetsleep is offline