Trip Introduction: The United Island Hopper via Honolulu and Kauai, Hawaii, USA on United Airlines and Alaska Airlines First Class

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The United Island Hopper is one of the world’s most unique travel routes. The route hops and skips its way across some of the most isolated islands in the Pacific Ocean. and is among some of the most popular flying for aviation fans that are into plain different routes. This trip outlines how I put together a trip through the United Airlines Island Hopper, along with what I saw along the way.


This post is one chapter on our trip on the United Island Hopper and to Oahu & Kauai, Hawaii, United States. This trip was redeemed through Alaska Mileage Plan, United Airlines Mileage Plus and Marriott Bonvoy. It was further enhanced through Marriott Bonvoy Elite Status. For more information on how this trip was booked, please see our trip introduction here. For other parts of the trip, please see this index.

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Trip Introduction: The United Island Hopper via Honolulu and Kauai, Hawaii, United States on United Airlines and Alaska Airlines First Class


Planning the Trip:

Right before the pandemic, in the fall of 2019, MrsWT73 mandated a winter holiday to get out of Vancouver’s wet and, unusually this year, snowy weather. We had previously made good use of our Alaska Two for One Companion Fares for the past four years.

Thanks to MrsWT73’s Alaska MVP Gold status, we’ve also made good use of First Class upgradable fare purchases that allow for an instant upgrade at time of purchase into the First Class cabin with the purchase of a higher class economy fare.

With no set destination in mind for these certificates, I eventually came up with a crazy idea of doing the United Island Hopper nested within an Alaska Airlines Companion Fare to Hawaii. Unlike many other travel bloggers in their twenties, I actually have a full time career that comes with a schedule, parenting responsibilities and other commitments that don’t make it so easy to undertake in such unusually crazy trips. With little convincing, MrsWT73 gave me a 36 hour kitchen pass away from the Honolulu portion of the holiday to do the UA Island Hopper while she stayed on in Honolulu relaxing and taking in some sun.

Planning Flights:

Flights from the Mainland to and from Hawaii

In order to get to Hawaii, for the Alaska Airlines Portion, I searched for available “U” space using Expert Flyer. I eventually found seats on the afternoon flight leaving Seattle for Honolulu. The outbound flight had a 5 hour layover in Seattle. We had American Express Centurion Lounge Seattle access so that dead time was taken care of as comfortably as possible.

For the return, we managed to find Alaska Airlines seats out of Lihue, Hawaii back to Seattle on the overnight with a short 2 ½ hour layover back home to Vancouver, Canada. We used an Alaska Two for One companion fare offer from the Canadian Alaska Airlines Mastercard and immediately confirmed ourselves into First Class at the time of booking on an upgradable fare. I credited these paid flights to Alaska Mileage Plan.

Booking the United Island Hopper:

I booked the United Airlines Island Hopper using United Airlines Mileage Plus points. The United Airlines Mileage Plus points were transferred in from Marriott Bonvoy. Thanks to a generous reciporacal relationship between the two, 120,000 Marriott Bonvoy Points became 55,000 United Mileage Plus points. At the time, there was a fall transfer bonus running which resulted in an additional 17,500 UA miles later awarded as a bonus for a total of 72,500 United Mileage Plus points transferred.

There was ample economy award availability on this route and I booked the United Island Hopper for 27,500 saver economy reward miles at fixed pricing levels before United switched to dynamic pricing.

I booked the return on the non stop United Airlines Guam – Honolulu B777-2 service from Guam back to Honolulu the next day. The round trip economy award came to 55,000 United Mileage Plus miles and $40 CAD in taxes and fees. The revenue price for the ticket was listed at $2,934.54 USD, making an award redemption an excellent value.

Since the United Island Hopper is all about taking in the view, I further secured an Economy Plus seat on the Hopper segment for $59 USD for the full 14 hours. I noticed some variability in the Economy Plus pricing with amounts ranging as low as $59, all the way up to $114 for the same routing and seat. Courtesy of the Marriott Bonvoy Titanium level status, I was an United Mileage Plus Elite Silver. As a United Silver, I had access to free Economy Plus at check in. However, I didn’t fancy being shut out of a window seat for the day. It turned out this was a wise move as there were only a few seats in the middle left in economy plus on my date. If you plan on taking the United Island Hopper, make sure you book your preferred seat well in advance.

Lastly, although the full 5 stop island hopper is only available 2 days a week, I ended up on the 4 stop hopper for schedule purposes, skipping the Kosrae stop in the Federated States of Micronesia. I would have loved to have done all 5 stops, but I also wanted to actually have a restful holiday and not be backtracking all over the place to get back to Honolulu to start the Hopper on one of the 5 stop trips. As a result, I took the shorter version, which was more than enough to experience it. This, I might add, is coming from the perspective of someone who is nearing the million mile mark for lifetime “tail in seat” miles flown and a regular consumer of flown miles for work purposes all throughout sparse Canada. I suppose I could have stopped over on the Micronesia islands for a day or two but also just opted for an out and back return.

Booking inter island travel:

Our flight into Hawaii arrived into Honolulu, Oahu and our flights out were from Lihue, Kauai. As a result, we needed to get from one island to another. I booked us on Hawaiian Airlines First Class Honolulu – Lihue. If you book early enough, the First Class inclusions of Priority Boarding, Free Checked Baggage and Seat Assignment are more than enough to make up for the add ones. We paid $106.19 USD per person for this segment in first class. I credited these paid flights to American Airlines AAdvantage.

In the end, the routing ended up looking like this after it was all put together:

YVR-SEA-HNL (Alaska Mileage Plan Companion Fare 2 for 1)
HNL-MAJ-KWA-PNI-TKK-GUM “The Island Hopper” (United Mileage Plus Award)
GUM-HNL (United Mileage Plus Award)
HNL-LIH (paid)
LIH-SEA-YVR (Alaska Mileage Plus Companion Fare 2 for 1)

The United Island Hopper nested into An Alaska Airlines Companion Fare

Planning Hotels:

In terms of hotels for this trip, we stuck with Marriott Bonvoy properties. This would allow me to start off towards Marriott Bonvoy Eilte status for the next year. We found a paid rate for $281 USD at The Sheraton Waikiki that offered a daily $50 USD food and beverage credit which was a great deal. Thanks to it’s convenient location, it was a great place for MrsWT73 to hang out in comfort while I did the United Island Hopper.

While I was on the United Island Hopper route it was down to the Westin Resort Guam or the Sheraton Laguna Guam Resort. I ended up at the Sheraton Laguna Guam Resort thanks to a softer nightly rate. I paid cash for this room at $264 USD. Sometimes, the Marriott Bonvoy program surprises you and I ended up with a complimentary suite upgrade finding myself in a massive suite courtesy of Marriott Bonvoy Titanium status. I rented a car through Hertz while on Guam and ended up in a small upgrade to a brand new Mazda Three.

For our six days in Kauai, we ended up at The Sheraton Kauai Resort located in Poipu, Kauai. As a Marriott Bonvoy Category 5 hotel, we were able to redeem two free night certificates courtesy of the American Express Marriott Bonvoy credit card, one free night certificate for achieving Marriott Bonvoy Platinum status at 75 paid nights against a hotel up to Marriott Bonvoy 40,000 points. We then redeemed two nights under the regular reward method for 30,000 points per night for 60,000 points. In total, our six night stay was free with the exception of the resort fees which were $30 USD a night at $4.49 USD in taxes for a total of $172.90. We applied Marriott Bonvoy Suite Night Awards to the room and were upgraded into a Luxury Ocean Front Room. I rented a car through Hertz while we were on the island and received a large Hertz President’s Circle upgrade to a Chevrolet Impala.

Our points and miles redemption summary:

In summary, we redeemed:

  • 60,000 Marriott Bonvoy Points – Sheraton Kauai Resort for 2 nights
  • 55,000 United Airlines Mileage Plus miles for the United Island Hopper – round trip
  • An Annual Alaska Two for One Companion Voucher for round trip Alaska Airlines Airfare Vancouver to Hawaii

I hope you’ll join us on our last trip before the global pandemic shut everything down worldwide only thirty days after we finished this trip.


If you have flown the United Island Hopper, how did you put it all together and did you stop anywhere on the way ?

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