Hawaii planning

When I first started nerding out on points years ago, I noticed that FlyerTalk.com forums were full of posts from novices pleading for advice for getting to Hawaii. The subject line was always, "HELP!!!!" and then continued with:

"It's my honeymoon so you HAVE to help me!  …And the honeymoon is in 10 days!  …And I want to fly direct to Maui from Omaha!  …And I want to be in First Class! …And I have 8,000 points total spread across six frequent flier accounts!" 

Needless to say there weren't many happy endings on those posts 😜

Well, now it's my turn to start sifting through all of that advice I skipped over all those years – I'm taking my first trip to Hawaii. My in-laws are there on a work assignment outside of Hilo, so we're going to try to get out to see them at the tail end of New York winter, when you're 110% sick of the snow and slush.

UPDATE: Trip report!

Here's a few things I learned:

• Flights to Hawaii are all during the day
• Flights from Hawaii to the East Coast are all 11-hour overnight flights, so a lie-flat seat would be ideal on that leg
• Most of the First Class seats to Hawaii are normal 38" domestic recliner seats
• A few airlines have lie-flat seats on flights from the East Coast (Delta, United), but you have to be really careful to make sure you're booking the right flight. (SeatGuru.com is your friend!)
• Delta's direct JFK service is Winter-only (ending 25 March). Their lie-flat Business Class is around $1700 round trip – less than half the cost of United's lie-flat service, and still cheaper than Hawaiian's domestic recliners. 

  

  As is so often the case, United is laughably more expensive for an inferior product

• An economy round-trip is around $800 on all the carriers, so Delta's First Class is essentially double that price. United and Hawaiian want a minimum of triple the economy price for first. 
• I still have around 100k United points, but after looking there's basically zero Saver rewards in First and spotty Standard reward availability on the non-stop flight. So that's 180k miles (per person, round trip) in lie-flat First on days I don't like, with a per-point redemption value below 1¢. (Remember, anything below 1¢ is a terrible deal). But it's irrelevant in any event because I don't have 360k points, even if I transfer in from Chase.
  
  

  

  You're going to need 180,000 miles AND flexible dates if you want an award seat on that non-stop flight

• Hawaiian airlines is slowly rolling out lie-flat First, but the rollout isn't complete until 2018. From this thread on Flyertalk.com, it sounds like their flights to Asia will get the lie-flat service first, but then The Points Guy posted that the JFK-Honolulu run will get the lie-flat seats starting Feb 2017...
  

  

  Hawaiian's new lie-flat seat (click to enlarge)

• You can use JetBlue points to redeem for Hawaiian Airlines flights but you have to do it over the phone and you get about 1¢ per point. Of course AFTER I did all of this research The Points Guy publishes a full guide to the various JetBlue/Hawaiian redemption values :) 
• Many carriers offer direct service to smaller Hawaiian cities like Hilo, but only from the West Coast. Most everything from the East Coast routes through Honolulu.
• If you're connecting through Honolulu to other parts of Hawaii, double-check the cost of booking that leg separate from your long haul. I saw several instances where a cheap island hop connection was adding $500 to my itinerary. 

What we did

Since there were no good point options we decided to pay for our flight. Once I actually priced out a split itinerary (Economy there, First on the way back) we'd only be saving around $300 a person by flying in Economy on the leg out there. For a 10-hour flight it seemed worth it to spring for First both ways. I booked through the Amex Travel portal so I'd get another bonus point per dollar in addition to the 3 points I get on airfare from my Amex Premier Rewards Gold card. During checkout, I noticed this (the framing of the window says I get 2x points from the Amex portal for Delta flights). If this is correct I'll earn 5 Amex points per dollar (8500 Amex points!) for my flight in addition to the 5 Delta points per dollar.  UPDATE: you don't get 2x as the window promises, just 1x. Details here. All told, I earned 8,000 Delta miles for this flight and 7,000 Amex points worth around $225.