Trip Booking – Hawaii, Fifth Attempt

My last post was about a cancellation to a long awaited Hawaii trip so it’s appropriate that my next one is on the same topic.

What was supposed to be a 9th anniversary trip to Maui and Hawaii earlier this year, over the course of 5 re-bookings, has now evolved to a 10th anniversary trip for P2 and I slated for June 2021. I’m banking on hope that the vaccine and more streamlined testing procedure will get things back on track in the next 6 months. Even so if things don’t get any worse we should be able to obtain COVID testing which meets the State of Hawaii requirements prior to our departure.

This iteration was booked for a combination of AA, DL, Hyatt and Hilton points:

Delta First Class CLE-SLC-OGG – 2 @ 86k each
Hyatt Regency Maui – 4 nights @ 25k/night
Hyatt Hana-Maui – 1 night @ 30k/night
Hawaiian Airlines OGG-ITO – 2 @ 7.5k each (United Miles)
Hilton DoubleTree Grand Naniloa Hotel Hilo- 1 night @ 50k/night
Hilton Waikoloa Village – 2 nights @ 58k/night
American First Class KOA-DFW-CLE – 2 @ 45k each (Web Special)

Cash value of the flights and airfare that is covered with points is about $9,000. The only major cash outlay now are convertibles rented from Hertz on each island for about $65/day on Maui and $95/day on Hawaii due to the one-way rental.

Outbound Flight

After pondering options on United as I did before I stumbled upon a flight from Cleveland (CLE) to Maui (OGG) with a connection in Salt Lake City (SLC). Cost was 83,000 SkyMiles each for First Class. It would have cost $1,151 each if paid in cash so the valuation is 1.4 cents per point (cpp).

The first leg from CLE to SLC is on an Airbus A319. There are only 12 recliner style first class seats in a 2-2 configuration.

While it’s not fancy, it’s not bad for a 4 hour flight. Of course the best thing about Delta is nearly every mainline aircraft, even narrow bodies like the A319 have seatback In Flight Entertainment (IFE) screens. I think this is one thing that sets Delta apart from the other legacy carriers who have mostly done away with built-in IFE in favor of content streaming to personal deceives.

After the 4 hour flight on the A319 we will arrive at Salt Lake City International Airport (SLC). I’ve never been to SLC and I’m quite excited to see the brand new terminal they have constructed. We do have a lengthy 5 hour layover so in addition to exporting the terminal we will also make an obligatory visit to the Delta SkyClub. Even though we are travelling first class, lounge access is not provided for domestic premium cabins. Instead I will be able to gain admittance with my Amex Platinum Card.

File photo of SkyClub at DTW Gate A18

After the layover we get to board our next flight to Maui (OGG). The aircraft will be an Aribus A330-300 with a “DeltaOne” cabin of 34 seats which convert to a lie-flat bed. While this aircraft sports one of Delta’s most premium hard products it is not considered a full DeltaOne service which is reserved for international flights only. Still even in COVID times it should be a comfy seat and better service than in the back.

The DeltaOne seats are arranged in a “reverse herringbone” 1-2-1 configuration. This means the outside seats face towards the window and not the aisle, a preferred configuration and the opposite of my neck-straining experience in the Virgin Atlantic A330 Upper Class seat.

Photo by Delta


After the 7-hour flight from SLC we will land at Maui’s Kahului Airport (OGG). We will pick up our convertible from Hertz and drive across the island to our first resort, the Hyatt Regency Maui located in the Kaanapali resort area.

Photo courtesy Hyatt

I had the fortune to visit this beautiful resort 20 years ago for dinner at the Swan Court. This sprawling resort has multiple pools, a water slide and direct access to the beach. I’m a big fan of swim up bars and this resort has an incredible “Grotto Bar” which you can access by swimming through a waterfall. Incredible!

Photo courtesy Hyatt

The World of Hyatt loyalty program is one of my favorites due to the high value of their points and easy transferability from Chase Ultimate Rewards. Four nights at this hotel was booked for a very reasonable 100,000 Hyatt points. These points were earned through a combination of the Chase Hyatt credit card and Ultimate Rewards points. The other great thing about Hyatt award bookings is the offensive resort fees are waived. In total using my Hyatt points saved me about $1,900 for just this one stay.


The “Road to Hana” is one of the most famous attractions on the island of Maui. It’s winding journey takes you through hairpin curves, past waterfalls and other incredible sights.

On my trip to Maui 20 years ago I traveled part of the road to Hana but wasn’t able to really take in all of it’s glory. So I was quite thrilled when I learned that Hyatt had taken over the former Hotel Travaasa located in Hana. So rather than spending 5 nights at the Hyatt Regency I modified the plans so we could spend one night at the Hyatt Hana-Maui Resort. Having a place to rest at the destination of Hana will allow us to split the journey into two days and really see everything the area has to offer. Plus this resort is amazingly beautiful in itself.

The Hyatt Hana Maui resort is classified as a Category 7 property so it cost 30,000 points per night. This is quite a good deal as the cash price for one night would have been $516.

Inter-Island Flight Maui to Hilo

A trip to the Hawaiian Islands would be underserved if only limited to one island. That is why after 5 days on Maui we will be taking a quick island hop flight on Hawaiian Airlines to the Big Island of Hawaii.

We chose to fly into Hilo (ITO) rather than the larger Kona (KOA) for a few reasons. Most important being the schedule of non-stop flights on Hawaiian from OOG to the Big Island. We want to maximize our last day on Maui so an evening flight was preferred. Using my favorite flight search engine, Google Flights, I was quickly able to determine that the only non-stop flight from Maui to Hawaii was the 6PM to Hilo.

Google Flights showed me the cash price of the one-way ticket $122 was each. This is obviously pretty cheap but since a big goal of award travel is to outlay as little cash a possible, I checked out point options. Since with the recent exception Southwest, none of the US mainland carriers service inter-island flights. Historically that has been the territory of Hawiian airlines so Delta, American and United have code share agreements with Hawaiian to provide inter-island flights for awards. Coincidentally, they each price their inter-island flights at a low fixed rate of 7,500 miles each way.

Hawaiian Airlines Boeing 717 used for inter-island service.

While this is a small amount of miles, given the often low cash prices of inter-island tickets this isn’t always a great use of miles. However, in this case the cash price of the ticket was $112 each which equates to about 1.5 cpp. This is about the bare minimum value I would redeem miles for. I do also have a small mountain of United miles I have been trying to use so I decided to redeem them for this short flight.

A second reason flying non-stop into Hilo is preferred because Hawaii is a large island and flying into Hilo allows for easier access to attractions on the east side of the island we would like to see before heading to Kona on the western shore.
Akaka Falls State Park on Hawaii island’s eastern shore.


The quick island hop flight from OGG to ITO should take about 25 minutes from wheels up to wheels down. We arrive at Hilo International Airport and have booked one night at the Grand Naniloa Hotel Hilo, a Hilton DoubleTree properly located about 1 mile from ITO.

Grand Naniloa Hotel Hilo seems nice and has a great view but seems to have less amenities as the larger resorts. It seems to be a bit of an older looking facility also reminiscent of 1960’s design. Still it should be a good place to stay for one night after our flight and before we set out for activities the next day.

The cost is 50,000 Hilton points compared to the cash price with resort fee of $355/night. This puts the valuation at 0.6cpp. While this seems low one thing you have to keep in mind is Hilton points are generally valued a lot less than Hyatt. One Hilton point is roughly 1/3 the value of one Hyatt point. This is reflected in the Amex MR transfer rate of 1:2 which is often raised to 1:2.8 or 1:3.


After the one night in Kona and activities in the area we will drive across the island to Kona where we have two nights reserved at the Hilton Waikoloa Village. The sprawling 62-acre resort features 1240 guest rooms, a private swimming lagoon along with water taxis and its own tram to transport guest from one side of the resort to the other.

To be honest a two day stay probably won’t even be enough to enjoy all the resort has to offer but it is too beautiful of a location to pass up.

The stay was booked for 58,000 Hilton points per night compared to a cash value of $580. This nets to about 0.5cpp which is on the low end, even for Hilton points but still worth saving the cash.

Return Flight

Sadly all good things must end so after eight days in paradise we must return home. That will be on American Airlines first class from Kona (KOA) to Cleveland (CLE) with a layover at Dallas-Ft. Worth (DFW). The flights were booked for 45,000 AAdvantage miles each. This was snagged an AA “Web Special Award” which is a promotional rate that American often runs. The ticket does come with some restrictions like it cannot be changed, however it can be cancelled and miles redeposited for free. Cash value of this ticket is $1,438 which yields a very respectable 3.2cpp.

The flight from KOA to DFW is seven hours in duration and will be on a Boeing 777-200. American has been standardizing it’s fleet so all aircraft of this type have 37 lie-flat seats in Business Class.

Similar to Delta, this is an internationally configured aircraft but while used on a domestic route many of the enhanced services would not be used. Still the “hard product” or the lie-flat seat and IFE are still top notch. These seats are also in the “reverse herringbone” configuration and offer spacious room and a good angle for views out the window.

After completion of the overnight flight from KOA we land at DFW in the early morning for another 5-hour layover before our last flight . Fortunately DFW is one of the largest airports in the world and offers a multitude of lounge offerings with arguably the best one being the American Express Centurion Lounge in Terminal D. A few years ago I had visited the DFW Centurion but since then American Express had opened an entirely new lounge elsewhere in Terminal D so I am looking forward to this experience.

After some relation in the lounge we will board a Boeing 737-800 that will take us home to CLE. The 737 is a workhorse of AA and many airline’s domestic fleets. AA has first class configured with 16 recliner seats in the standard 2-2 arrangement. Unlike, Delta, as part of AA’s fleet update, they have been removing personal IFE screens it’s narrow body aircraft so there is a good chance we will have to BYOD (Bring Your Own Device) if we desire entertainment. Still it’s tolerable for about a 2 hour flight.


Obviously in light of the current state of the world this trip is a bit of wishful thinking but if things finally start to turn the corner and we will be able to meet testing requirements for entry to Hawaii this should be a pretty epic trip.

*Hilton points normalized at 1:3

Points wise it does take a chunk out of my cache but at an overall 1.9cpp valuation I believe it is a good use of points for what is sure to be a memorable trip.

4 thoughts on “Trip Booking – Hawaii, Fifth Attempt

  1. Hi Mike – just found your blog and your Hawaii posts are very inspiring. My fiancé and I are planning a 10-12 day honeymoon in Hawaii. We’re looking to stay at the Andaz (5-8 nights) and Hana-Maui (2 nights) resorts and may possible fly over to the Grand Hyatt Kauai resort for a few nights (2-4). We’re newbies at the travel hacking game but our 2022 wedding will by at a Hyatt property and we opened a Hyatt cc to charge all of our wedding expenses. We currently have about 200k WoH points and 9 qualify nights. We expect to charge another $15k in the near future, giving us 6 more nights. I belive we need 16 nights after that to get to Globalist. What’s the best way to reach Globalist before the end of the year? We have a couple of Cat 2 hotels near us. Should we use 8k points/night and book the 8 nights? We’re hoping to book all of our Hawaii nights using points.


    1. Thanks Tom. Glad you appreciated it. Sounds like a great plan. I don’t think you will miss much skipping Kaanapali in favor of Kaui. We chose not to island hop at the time due to the additional COVID testing that was required.

      As for a fast track to Globalist status there was a promotion reported a few months ago that you can call one of the hotel service desks and they have an offer to reach Globalist in 20 nights. More details can be found here:

      A cheap mattress run might do the trick to close the gap. I assume you got the WOH offer where you got 2X qualifying night credits so 8 should do it for you. Even if you can find a cheap Category 1 for 5k/night or a cheap cash rate it might be worth it. I’d lock something in soon though because rumors are circulating again that Hyatt will finally be going to peak/off-peak award pricing.


  2. Thanks for the tips Mike!

    We don’t have any Cat 1 5k per night hotels near us. We do have a Cat 2 8k per night hotel close by we could physically do a mattress run. What are your thoughts on doing a “ghost” mattress run at Excalibur or Luxor and checking in via the app?


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