Trip Introduction: Pearl Harbour, The First Lady of Waikiki, Honolulu and Wailea Maui, Hawaii, USA via Alaska Airlines First Class

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Like our last trip, this particular voyage was about maximizing offers and redemptions to put together a reasonably priced holiday filled with value. We used Alaska Airlines Mileage Plan to redeem against upgrades in to First Class, a 3 for 2 hotel stay with a premium Fairmont hotel, and paid for a First Class fare between the Hawaiian Islands in order to take advantage of paid baggage fees. We ended up with a great value luxury trip for not much more than economy.


Trip Introduction: Pearl Harbour, The First Lady of Waikiki, Honolulu and Wailea Maui, Hawaii, United States of America via Alaska Airlines First Class.


Trip Background:

To This:

Trip Planning and Constructing the Trip:

I put together this trip designed to use up some outstanding vouchers and credits that I had collected along the way. Always a great deal, we used up a $99 two for one companion voucher for Alaska Airlines, courtesy of the Canadian Alaska Airlines MBNA Mastercard. These two for one vouchers can only be purchased into economy class but there are ways to further upgrade these tickets. After the purchase, we then upgraded the two economy segments into First Class for 15,000 Alaska Airlines Mileage Plan miles each way. Our upgradable economy class tickets came to $554.94 in fare and $48.05 in taxes totalling $602.99 USD for the first ticket, and $99 USD + 46.37 taxes totalling $145.37 for the second ticket, totalling $748.36 USD and 60,000 Mileage Plan Miles for two round trip tickets in First Class.

For the first portion of the trip, we had the Westin Moana Surfrider on our list for quite some time. We ended up staying there on a terrific rate that we stumbled on at $177 USD per night in the classic building. We were there for 3 nights, at a total price of $531 plus taxes.

Getting in between the islands, we chose Hawaiian Airlines for our flight between Honolulu – Maui. As we had to check a bag, instead of paying a baggage fee, we opted for a first class ticket which included lounge access and two free checked bags. We paid cash for these fares at they came to $162 USD per person one way.

We also stayed at the Fairmont Kena Lani on a Fairmont Premier stay 3 – pay 2 voucher which we achieved on a Fast Track promotion thanks to Air Canada Aeroplan Elite Status that I had in 2013. Fairmont was ever so kind to “soft land” me along with everyone else in 2014 when I had unused certificates – extending my status another year with them despite no qualifying stays. Our room rate there was $489 USD for two nights, with the third night free. This brought the rate down to an average of $326 USD a night; an excellent rate for this particular property. We also received a double category upgrade from a mountain view to a partial ocean view.

For a total of $2,582 USD or $1,291 USD per person, we had a weeks’ stay in Hawaii including round trip first class tickets, accomodations and our inter island connecting flights. While not the best rendemption out there, it was pretty reasonable for Hawaii, which can tend towards the expensive side for a beach holiday.

The Routing:

Our routing ended up looking like follows:

BLI-HNL (paid)
HNL-OGG (paid)
OGG-BLI (paid)
Our Routing Ended Up Like This

This post is one chapter on our trip to Honolulu & Maui, Hawaii, United States of America. This trip was redeemed through Alaska Mileage Plan and Fairmont President’s Club. 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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I hope you enjoy following along on another adventure to one of the United States’s greatest warm weather destinations.


If you’ve designed a trip around an Alaska Airlines Companion Fare, how did you go about doing it?

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