Hawaii 219: Intro

EWR-HNL BusinessFirst
St. Regis Princeville Resort, Kaua’i
St. Regis Princeville Dining
Kaua’i – The Garden Island
Off to Maui
Four Seasons Maui at Wailea
The Food at the Four Seasons
The Rest of the Four Seasons Maui at Wailea
3 Things To Do on Maui
Aloha, Hawaii


“Let’s get married in Hawaii!!” I think that’s what Joann and I said to each other when we first started planning the wedding. That’s how this all started. While I was obviously happy to help plan a wedding, I was even happier when I was trusted with relegated to planning the entire travel portion of this production. This was in early 2011 and I would have just over a year to figure out our main flight to Hawaii and 100% of the honeymoon.

At that point in time, we didn’t have as many miles as we do today which is over 1.6 million miles/points. Basically, our only options were Economy awards on Continental or wait for a decent fare and buy tickets. Ideally, it would be smart to have miles spread out across other airlines like American or Delta just to have more options, but that was not the case. This was before I really started going hard in the points game. We decided to redeem the modest amount of miles we had for 2 round trip award tickets in Economy Class (40k each). Fares from the East Coast to Hawaii usually range from $650-850 so we felt we were getting a pretty good value.

Fast forward to May 2010 when Flyer Talk had just broken news about a fare sale to Hawaii. Fares from the East Coast were $500 and I was finding all sorts of availability. This was definitely a “Buy now, figure it out later” kind of situation – thanks for the 24 hour grace period, CO! I alerted all of our friends and family that were going to attend our wedding about this. As for Joann and me, we already had tickets. I debated for a bit and ultimately decided to cancel our award and buy the $500 tickets. I always like to earn miles and, as a CO Gold Elite, this fare would be earning me 20k redeemable miles. We can save all these miles for some aspirational trip in a First Class cabin one day!

A few months later, after a nice haul of credit card bonuses, we were looking at over 200k new CO miles. Since we’ve never flown in First Class together before, I decided that we had enough miles to blow on an upgrade. For 17.5k miles per person each way (70k total) and a copay, we could be riding in CO’s BusinessFirst cabin. Not a bad way to spend 11 hours in the air.

I’ll save the hotel details and other things I planned as I get to them because there was no real hustle involved like paying for all the hotels in points from credit card bonuses. All those points are still in our accounts just waiting to be used. There is a lot more to this Trip Report like Oahu hotels/resorts, inter-island flights, Kauai & Maui accommodations and activities, and finally our flight home. It was an amazing and exciting two and a half weeks so stay tuned for the next installment which will be our EWR-HNL Continental BusinessFirst flight