2021 Hawaii Trip Part I: Planning Around an Expiring Deal

Kalalau Lookout, Kauai

I’m going to post a new (old) trip report over the next few weeks. This will chronicle our empty nester trip to Hawaii (without the kids) in July 2021. I hope you enjoy it. The pictures were obviously taken without knowing at the time they would be used in this blog so I apologize in advance for my suboptimal photos.

Can you remember what things were like in February 2021? Many of us had received our first or second Covid vaccination, the winter wave had peaked, we had never heard of the Delta or Omicron variants and the Covid numbers were headed downward sharply. Around this time, I started planning some trips. We were cautious about heading overseas (at least to Europe) as there were still a lot of travel restrictions in place.

Flashback (within this flashback) to August 2019. I called Hilton to book some free award nights using certificates (which can’t be booked online) and the agent said “please stay on the line for a special offer.” Like an idiot, I stayed on the line. The offer was a deeply discounted 5-night, 6 day stay with a rental car included at one of five places – Vegas, Orlando, Myrtle Beach, Hilton Head or Hawaii. Of course, there was a catch – a 2-hour timeshare presentation.

I had no interest in the first four places but inquired a bit more about Hawaii options. We had just been to Maui, but I was interested in going to the Big Island and/or Kauai. My wife had been to the Big Island when she was 17, but I had never been to either place. I ended up buying the $749 offer for the Big Island, with a stay at the Hilton Waikoloa Village and 10,000 Hilton points to sweeten the deal. The most important thing I negotiated was allowing us two years to use the offer instead of the usual one year (as we had just been to Maui a few months earlier). The deal required half payment at the time of purchase with the remainder paid when we booked the actual stay. The two year expiration really paid off when Covid hit a few months later.

Hilton Waikoloa Village

I remembered this deal as I looked at options for summer 2021 travel. It expired August 3, 2021, so we would need to book and stay sometime before this. We decided I should look at flights in July and try and work in this Hilton stay along with a stay at the Grand Hyatt Kauai to take advantage of my Globalist status at one of the premier Hyatt properties in North America.

I initially tried to book business or first class flights, but soon found it impossible for any dates in July. Eventually, I found space in economy on American Airlines (ATL-DFW-KOA) which would get us into Kona on the Big Island early afternoon on July 4th. I ended up booking this with expiring Cathay Pacific AsiaMiles for 27,000 per person. As it turned out, AsiaMiles eventually extended my expiration date so I could have used just 22,500 American Airlines miles. Coming back, I found space in United economy from Kauai (LIH-DEN-ATL) for 22,500 per person and transferred Chase Ultimate Rewards points over to book the flights for July 13th arriving on July 14th.  The connections would allow us to visit American Express Centurion lounges in Dallas and Denver to fuel up for the lack of food on these economy flights.

Denver Amex Centurion Lounge

With the flights booked, I turned my attention to the hotels. The Hilton Waikoloa Village was available from July 4th-9th. The rep assured me that I also had a rental car booked with National included in my stay. I was unable to take advantage of any Hilton Diamond benefits as I was on a timeshare preview stay.

I booked a flight for July 9th from Kona to Lihue, Kauai on Hawaiian Airlines using 7,500 Delta SkyMiles per person (instead of the $150 per person cash price). As it turned out, I had to change this to a connecting flight when the schedules were tweaked, but it was easy and only added about 45 minutes to the journey.

Hawaiian Airlines Interisland 717-200

In early March, I found availability at the Grand Hyatt Kauai (25,000 points per night – Category 6 at the time), but I was also able to attach a suite upgrade certificate.  My Hyatt concierge handled the follow-up emails with the resort as they technically did not re-open from Covid closure until early April so we could not attach the upgrade certificate until someone at the resort could confirm the space.  By early April, we were all set.  The resort emailed me in advance to see if we had any questions and whether we were celebrating anything (our 25th anniversary was in May).

Grand Hyatt Kauai

Now we were set. Fly out July 4th early morning. Spend five nights on the Big Island. Fly over to Kauai and spend four nights there before flying home on the 13th overnight. Join me over the next few weeks as I post this trip report. While the covid restrictions have changed a lot, almost everything we did was outdoors so you won’t see many differences between summer 2021 and summer 2022 (except even more people traveling). I hope you enjoy the trip report and please let me know if you have any questions about how we booked or the trip itself.

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