This trip introduction describes how I put together my winter holiday trip to the Hawaiian islands. By using a few tricks that are accessible to anyone, I was able to save about $1,000 USD off my first class airfare, along with getting seven nights for free at the Sheraton Maui resort and spa [without attending a timeshare sales presentation]. I was able to enjoy a great relaxing holiday, along with finally getting to experience the Road to Hana. Read on to see how I put this particular trip together.

Trip Introduction: Black Rock Diaries, A Maui Escape, Hawaii, USA

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This trip was borne out of the need to take a bit of a sunny holiday at the start of winter break. While I was researching destination options, by complete chance, I happened across some excellent Marriott Bonvoy points redemptions rates at the Sheraton Maui Resort and Spa.

Rooms at the property were redeemable for as little as 40,000 Marriott Bonvoy points per night. This would allow us to redeem points at an excellent rate, in addition to using free night certificates that came annually with the Marriott Bonvoy American Express credit card. This pretty much locked in the deal for us, and we planned our trip around excellent hotel reward availability.

Booking Flights:

Hawaii is a long way from my home in Vancouver British Columbia, Canada. As a result, business or first class was the only way to go.

I had access to one last Alaska Airlines Companion fare, courtesy of the now defunct Alaska Alaska Airlines MBNA Mastercard. If you’re reading from the United States, this Companion Fare remains available with the Alaska Airlines Visa Card offered by Bank of America. These fares allow for a second companion fare to be purchased for just $99, plus taxes and fees.

It can sometimes be a little tricky to find upgradeable Alaska Airlines space. The Companion Fare is normally only valid on economy tickets, but it doesn’t preclude you from using upgrade instruments to upgrade into First Class.

Alaska Airlines MVP and higher members are allowed to purchase fares that offer an instant upgrade into First Class. The only condition is that the fare has to be purchased into K Class, and that there is available “U” space to confirm an upgrade into.

On the Alaska Airlines website booking page, if you toggle the Alaska MVP mileage plan level and look for a blue and white F in the fair types, you’ll be able to purchase and instantly upgradeable first class fare. With a little guess and check, we were able to locate upgradable space to Hawaii, USA that aligned with our great rate hotel stay.

Unfortunately, I wasn’t able to find space returning direct from Maui to Seattle. As a result I ended up flying Maui to San Diego to Seattle. While it was about 2 1/2 hours out of the way, for a large person like myself, it was well worth it to stay in a first class cabin.

For this inconvenience related to the indirect routing, I would end up with a few thousand more Alaska Airlines Mileage Plan miles as a result of the extra distance flown. Alaska Airlines K fares earn 125% into Alaska Airlines Mileage plan, in addition to Alaska Airlines MVP Elite bonuses between 50-125% at the time of this trip.

The price for both of us using the companion fare came to US$1,900. That’s not a bad price for a confirmed seat for two persons in First Class, without having to gamble on hoping for an upgrade.

When compared to the original price, the Alaska Airlines Companion Fare offered us a savings of about $1,067 USD. Purchased separately, the ticket worked out to about $1,500 USD per person, or $3,000 USD for two. The Alaska Airlines Companion Fare got the same ticket down to $1,933 USD; a better deal.

I’ve been successful with carefully planning the use of our Alaska Airlines companion two-for-one fares. We’ve mostly redeemed them on flights to and from Hawaii but also were able to use them on our flight to Anchorage, Alaska, USA.

We’ve saved a substantial sum of money and have usually travelled in first class with some careful planning. In the end, the trip routing looked like this…

Although this trip actually departed from Vancouver, Canada, I have reviewed the short haul flight on Alaska airlines Vancouver – Seattle so many times. Since it doesn’t actually offer any in-flight service, I have elected not to review it again within this trip report.

Planning Hotels:

While I was researching options for an early winter getaway, I happened across some excellent Marriott Bonvoy reward availability at the Sheraton Maui Resort and Spa located near Black Rock in Kaanapali – Maui, Hawaii, USA.

I’ve previously stayed at the Sheraton Resort and Spa Maui before. Although it’s an older property, it offers an excellent beachside location with great access to restaurants in Kaanapali on the shores of a fantastic world class beach.

The hotel has excellent access to snorkelling from shore at Black Rock, which adds value to any stay.

I located the rates using the Marriott Bonvoy flexible date calendar which showed the first week of December being ideal for a visit.

We ended up staying a total of seven nights. I couldn’t get the sticky Marriott Bonvoy booking engine to accept my American Express Marriott Bonvoy free night certificates. As a result I made two back to back bookings.

The first booking I used using Marriott Bonvoy American Express Marriott Bonvoy credit card free night certificate. Each of these certificates were good for up to 35,000 points. I used an additional 6,600 points to top off this reservation.

For the next longer stay reservation I ended up redeeming 166,400 Marriott Bonvoy points for five nights. Marriott Bonvoy members get the fifth night free when redeeming four nights. This brought down the average nights stay to 33,280 Marriott Bonvoy points, which was an excellent deal.

While the rates had slightly increased from the calendar that showed them at 40,000 points by the time I was able to confirm a reservation, it was still an excellent deal overall for a Hawaii Marriott Bonvoy redemption.

The regular paid rate for my stay during my visit was US$542 per night [including the resort fee].

However as a Marriott Bonvoy Titanium level member, we were given an upgrade to the best available room at check-in. Fortunately, the Sheraton Maui resort and spa still respect some elements of the Marriott Bonvoy program.

We would end up getting upgraded into our Ohana Double suite valued at $1,128 a night. This represented an excellent value.

I couldn’t have been happier with the value represented from this day stay. While it can be sometimes difficult to redeem American Express Marriott Bonvoy free night certificates, along with our points, I’m confident I came out quite well ahead with this redemption.

Planning Activities:

The trip was mostly designed around relaxation. We didn’t aim to get in too many activities during this trip. We ended up spending most of our time relaxing on the resort.

We did take one day to drive the famous Road to Hana that had eluded us for many years, in order to explore the black sand beach.

We accessed this via a rental car from Hertz Maui international airport, and self drove our way out to Hana.

Our visit to the Waiʻānapanapa State Park was another glimpse into the beautiful countryside on the Hawaiian islands. Hawaii has so many different areas to discover and you really have to marvel at its beauty.

This trip was enough to hit the spot for a relaxing stay. It struck the right balance of not being too expensive on the wallet, great relaxation along with a little sightseeing.

My Thoughts on Planning the Black Rock Diaries:

Aside from the headache of finding Alaska Airlines upgradeable first class reward seats, this trip was pretty easy to put together.

I was fortunate to find some really good Marriott Bonvoy award availability that would allow me to burn up my free night certificates courtesy of the Marriott Bon Voy American Express card, along with a great Marriott Bonvoy stay redemption.

Trips like these show that you have to do a little research in order to find these bargains.

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Have you had a great Marriott Bonvoy reward redemption lately ?

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