We’re heading to Hawaii in less than a week!

This vacation has been a work in progress for some time now but nevertheless, I’m glad it’s been taken care of and all that’s left is to hop on a plane and enjoy it!


Sneak Peak: 

12 days in the Aloha State 

Oahu, Big Island and Maui 

Hilton and Marriott Properties 

Centurion Lounge @ SFO 

Plumeria Lounge @ HNL


Bells & Whistles: 

As mentioned above, piecing together this trip took a little while but I’m extremely happy and excited to be going back to the Aloha State.

(Side note: This will be our little one’s first “big trip” and by big I mean longest flight as well as the first encounter with time changes.  Can you tell that I’m not-so-excited about that? We’ll see what happens!)

It’s been almost 4 years since we were last in Hawaii – we were actually there for our honeymoon and it was my first time on the islands.  Needless to say, I loved every moment of it and I’m glad to be heading back so soon.  I say so soon because well, let’s face it, Hawaii is damn expensive and most people, I would think, make subsequent trips to Hawaii (or any other expensive destination) once they’ve taken a handful of years to save up (or pay off the last trip j/k).

The beautiful thing about earning Miles and Points is that it allows you to venture back to those once cost-prohibitive destinations.  What was once a matter of not being able to afford it, is now a matter of how fast you can accumulate said Miles and Points to get you back there.  



Getting to Hawaii is usually half the financial battle.  Fares from YYZ to the Islands can run anywhere from $500 all the way up to $1000+ per person and that’s heavily dependent on when you fly, which carrier you use and which island you fly into.   

For this trip, we found a great cash fare, despite it being March/Spring break, so it made more sense to pay out of pocket for the flights than it was to redeem Miles/Points for it.  That being said, award bookings were either hard to come across or the itineraries were not convenient for the little one.  There are some sweet spots when redeeming Miles/Points for Hawaii but I’ll save that for another post! 

All in all, ouropen jaw flight to Hawaii cost us $1,200 for 3 travellers after redeeming $250 through Expedia For TD.

**I’ll be writing up a post talking about the other spectrum of credit cards that offer Fixed Value Points.**  

Because we’ll be island hopping on this trip, this meant that we would ultimately have to get across to the other islands.  The intra-island flights via Hawaiian Airlines are pretty phenomenal and are extremely frequent.  Prices range from$90-$125+USD depending on which islands you’re traveling to and from as well as if there are any promotions.  For this trip we redeemed points for flights on Hawaiian Airlines between Oahu and The Big Island as well as The Big Island and Maui.   

Hawaiian Airlines

All in all for our two intra-island flights, the total costs were (15,000 Delta SkyMiles and 15,000 HawaiianMiles and less than USD$25 in taxes/fees. 


The Hotels

Our first stop will be in Honolulu on Oahu, which is considered to be “The Heart of the Island”.   We’ll be staying at the expansive Hilton Hawaiian Village and needless to say, this place is massive.  It’s situated on 22 acres of oceanfront, has 5 pools and 20 restaurants and bars and much more.  From what I’ve been told, penguins frolic the grounds which I’m sure our daughter will love.   


Hilton Hawaiian Village

Our next stop will be The Big Island which is the youngest island in the Hawaiian chain.  We’ll be staying in Hilo which is situated on the eastern side of the island and sits at the base of two shield volcanoes, Mauna Loa and Mauna Kea. Here, we’ll be staying at the Grand Naniloa Doubletree which sits on Hilo Bay 

Grand Naniloa Doubletree


Wailea will be our final destination which is located on the south west coast of Maui.  Here, we’ll be staying at the Residence Inn Maui Wailea which is a stones throw away from the many luxurious resorts on the island including, The Grand Wailea, Andaz Maui and Four Seasons.  While not a resort in itself, it does have one and two bedroom suites as well as full kitchens which we were fond of.

Because of its location and the fact that its on Maui, this particular Residence Inn is considered a Category 8 hotel and goes for 40,000 Marriott Points a night.  We’ll be staying for 4 nights but since Marriott gives you your 5th night free, I redeemed for 5 nights and tacked it on at the beginning of our stay to guarantee us the early check-in, if you will, on our first day. 

Residence Inn Maui Wailea


Wrap Up: 

From active volcanoes and coffee farms, to wet tropical and polar tundra climate zones, as well as black sand beaches and crystal blue waters (not to mention the home of Jurassic Park) – Hawaii has got it all.

I’ll be breaking down the trip when we return and I’ll talk about all the exciting things that the Islands of Aloha had to offer. 


Until next time…  


~Keep Wandering 

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