Booked: Aloha, Bula, and Kia Ora

Just over a week after returning from my November round-the-world trip, the adventure is set to continue with a couple of weeks spent hopping through the Pacific Ocean with my girlfriend Jessy in tow. Here are all the details of the next trip I’ll be embarking on shortly, where I’ll be hitting up Hawaii, Fiji, and New Zealand.

The Trip

I was instantly charmed by New Zealand when I swung through Auckland for two days on my round-the-world trip back in February, and I had immediately decided, right then and there, to plan another New Zealand trip with Jessy as soon as possible.

That became the main motivating factor of this December trip, which happens to be the first time in a while that Jessy has enough time off from her graduate studies program to join me on a long-haul journey somewhere. 

Of course, as I always do, I tried to think of some interesting stopovers and layovers along the way to or from New Zealand. And since Jessy had always clamoured for us to go to Hawaii as well, I decided to see if I could fit in a few days there.

While I had originally booked a set of Air Canada business class flights into Honolulu, the schedule change resulting from the Boeing 737 MAX fiasco eventually compelled me to change our destination to Maui instead, which I hear offers much more in the way of natural beauty and scenic hikes, in addition to some splendid beaches of course.

Maui, Hawaii

Maui, Hawaii

After four days in Maui, the long journey south to New Zealand begins. Here, I opted for a rather unconventional routing: a “mini-island-hopper” sequence that sees us flying down to Nadi, Fiji with a one-hour stop in Kiritimati, Kiribati (also known as “Christmas Island”, but a different Christmas Island from the more well-known Australian territory). After a 23-hour layover in Fiji, we’ll continue down to Auckland, New Zealand.

(This was all booked as a single Fiji Airways redemption, which I’ll expand upon further in the section below.)

Finally, the bulk of our trip takes place over the course of nine days in New Zealand – although I would’ve definitely loved to have even more time there to drive the entire North and South Islands. 

Instead, with only nine days to work with, I decided to first spend two days in Auckland exploring the city again and adjusting to the time zone, before we’d fly down to Queenstown and use it as a base to explore the otherworldly natural beauty of New Zealand’s South Island.

Queenstown, New Zealand

Queenstown, New Zealand

We’ll be driving from Queenstown down to the scenic lake town of Te Anau, from which we’ve booked a day tour of Milford Sound, which includes a boat cruise of the region’s stunning fiords and a guided hike on part of the famous Milford Track as well.

(Unfortunately, hiking the entirety of the Milford Track – often described as “the finest walk in the world” – is something that needs to be booked almost a year in advance, so I’m afraid it’ll have to wait for sometime in the future, and probably when Jessy and I are more accomplished hikers than the mere amateur interest we take at the moment.)

Milford Sound, New Zealand

Milford Sound, New Zealand

The next day, we’ll drive back to Queenstown and spend the night there. Then, for the next three days, we’ll head north towards Mount Cook and Lake Tekapo, both of which offer ample hiking trails and gorgeous scenic views that visitors are able to explore at their own pace. 

We’ll finish the trip off with a day and a half spent relaxing in Queenstown, which I’ve heard many people say is one of the most beautiful towns they’ve ever visited, especially during the long nights of the southern summer.

Finally, as part of the return journey on Aeroplan that I booked, I managed to schedule in a 24-hour layover in Christchurch before heading to Auckland and then flying back across the Pacific, so I’m happy to get the chance to explore a bit of the South Island’s largest city as well.

The Flights

Before I talk about the flights in detail, I want to mention that this itinerary was by no means an easy one to book at all.

A trip similar to this, involving Hawaii, New Zealand, and some islands in the South Pacific, is one that I very often hear about people wanting to book, but the reality is that the limited flight networks and award availability make it quite a tough trip to piece together. 

In my case, even having planned much of this trip about nine months in advance, I still ended up with more economy class flights on the agenda than I’d usually like, and I’ve probably spent more miles and gotten less “on-paper” value than a “simple” business class round-the-world trip to Europe and Asia would’ve gotten me.

The point is: the Pacific Ocean is definitely not an easy part of the world to explore on points, and you really must work for it!

Fiji Airways A320 business class

Fiji Airways A320 business class

With that being said, let’s take a look at my outbound journey first. There are no major award programs that let you book a stopover in Hawaii on a one-way routing to New Zealand, so I had to break this into two separate redemptions: one from Montreal to Hawaii, and then another from Hawaii to New Zealand.

(In theory, I could’ve combined the outbound and the return into a single Aeroplan round-trip with a stopover in Hawaii, except for the fact that Air New Zealand’s Hawaii–Auckland flight almost never has any award space, and any other routing would’ve fallen afoul of the maximum permitted mileage.)

From Montreal to Hawaii, I had initially chosen the relatively simple routing of Air Canada business class via Vancouver, for 40,000 Aeroplan miles per person. But then the Boeing 737 MAX fiasco happened, which resulted in a few things being shuffled around: while I’d get to avoid an overnight layover in Vancouver, the flight from Vancouver to Maui was now on Air Canada Rouge (ugh!), and I’d also only arrive in Hawaii late at night.

Nevertheless, it was still the most comfortable way to fly out there, since all of the United Airlines flights were showing economy class only, and as much as we like to give Air Canada Rouge hard time… well, it’s better than economy.

Indeed, that lesson will surely be very keenly felt on the way from Hawaii to Auckland. 

Here’s the story: Fiji Airways, an Alaska Airlines partner, serves Honolulu twice a week. But one of these flights is operated via an intermediate island – a place called Kiritimati, or Christmas Island, part of the Republic of Kiribati spanning over 3.5 million square kilometres in the central Pacific Ocean. 

Once I had taken notice of this flight’s existence, I immediately thought back to the memories from my United Island Hopper adventure earlier this year.

And I must’ve been quite desperate indeed to rekindle those memories with a one-hour stop in Kiritimati, because I went ahead and booked the whole Hawaii–Kiritimati–Nadi–Auckland journey for 45,000 Alaska miles per person in mixed economy and business class, with the hope of upgrading the Hawaii–Kiritimati–Nadi segment to business class if it opened up later… except it never did.

(I haven’t told Jessy that we’re spending a grand total of eight hours hopping through the middle of nowhere in the backseats of a Fiji Airways 737 yet. Sorry Jessy.)

Thankfully, the return journey from New Zealand will be a much more comfortable ride. As part of the overall Aeroplan redemption from Queenstown to Toronto, which cost 80,000 Aeroplan miles per person, I eventually managed to snag a very rare award in Air New Zealand business class from Auckland to Los Angeles – but it certainly didn’t come easily.

At first, I had booked a very convoluted routing on Singapore Airlines and Air Canada via Singapore and Seoul. At this point, I decided to set a few ExpertFlyer alerts for Air New Zealand business class space, so that I could make changes if they later opened up.

map (9).gif

Several months later, Air New Zealand opened up some space on their Auckland–Tokyo Narita flight that day, so I made the change to shorten the journey significantly…

map (10).gif

And then another month later, Air New Zealand opened up space on Auckland–Los Angeles, so I made another change to make it the most efficient ride home. We’re ending the journey in Toronto (following an Air Canada business class flight on the Dreamliner from Los Angeles) to spend the Christmas holidays with Jessy’s parents, so we didn’t want to be flying around for any longer than we needed to be. 

Finally, I just had a few short one-way segments to book: Maui–Honolulu, which was a very cheap US$39 fare on Hawaiian Airlines, and Auckland–Queenstown, which was a slightly more expensive $90 on Air New Zealand.

I had always known from others’ experiences that a trip through the Pacific Ocean was a rather difficult one to pull off on points (especially if you want business class on the longer flights), but now I know that from my own experience.

You’ll need to plan well in advance, be prepared to book less optimal routings and make changes later, and be willing to part ways with larger sums of points than if you had decided to take an “easier” trip instead (and even then, you may simply have to make do with economy class in order to go where you want to go).

My overall routing therefore looks as follows: 

  • Montreal to Vancouver on Air Canada, departing 7:15am and arriving 9:46am, business class

  • Vancouver to Maui on Air Canada, departing 6pm and arriving 10:15pm, business class


  • Maui to Honolulu on Hawaiian Airlines, departing 9:10am and arriving 9:48am, economy class

  • Honolulu to Kiritimati on Fiji Airways, departing 12pm and arriving 3:15pm the next day, economy class

  • Kiritimati to Nadi on Fiji Airways, departing 4:15pm and arriving 8:05pm, economy class

  • Nadi to Auckland on Fiji Airways, departing 7pm and arriving 10:10pm, business class


  • Auckland to Queenstown on Air New Zealand, departing 3:40pm and arriving 5:35pm, economy class


  • Queenstown to Christchurch on Air New Zealand, departing 5:40pm and arriving 6:40pm, economy class

  • Christchurch to Auckland on Air New Zealand, departing 6pm and arriving 7:25pm, economy class

  • Auckland to Los Angeles on Air New Zealand, departing 10:55pm and arriving 2pm, business class

  • Los Angeles to Toronto on Air Canada, departing 10:35pm and arriving 5:58am the next day, business class

The Hotels

For this trip, I needed to book accommodations for:

  • Four nights in Maui

  • One night in Fiji

  • Two nights in Auckland

  • Three nights in Te Anau

  • One nights in Queenstown

  • Three nights somewhere around Mount Cook and Lake Tekapo

  • One night in Christchurch

In Maui and Fiji, I had no troubles upholding my loyalty to Marriott Bonvoy. While I wasn’t overly impressed by any of the Maui properties, I thought the Wailea Beach Marriott Resort would do just fine for a relaxing beachside getaway, especially because I was able to find all four nights at the off-peak rate of 40,000 Bonvoy points per night for this Category 6 property.

Wailea Beach Marriott Resort & Spa, Maui

Wailea Beach Marriott Resort & Spa, Maui

With cash rates nearing US$500 per night, I felt I was getting a great deal. Furthermore, I was able to extract maximum value out of the 40,000-point free night certificate I earned for achieving Titanium Elite status this year, meaning I only had to pay the 40,000 points for three nights.

(The resort also has a waterslide as part of their pool, which I intend to go on at least a few dozen times.)

On the downside, the Wailea Beach Marriott imposes a nasty resort fee of US$38 per day – gross. Let’s just say I’ll be keeping my eyes open for any in-room deficiencies or service failures that could somehow be used to justify a waiver of those predatory resort fees.

Over in Fiji, the city of Nadi is where most tourists pass through, and there are a wealth of hotels that seem to fall into that “good-but-not-great” category.

I decided to stay at the Marriott Fiji Resort Momi Bay mostly because of its overwater villas, which did a much better job of catching my eye than the other Marriott resorts on Fiji (well, except for the Sheraton Resort Tokoriki Island, but I thought that the two-hour boat transfer required from Nadi would be far too inconvenient for our short one-night stay). 

Marriott Fiji Resort Momi Bay

Marriott Fiji Resort Momi Bay

I booked a night here at this Category 5 property for 30,000 Bonvoy points, again at the off-peak rate, which felt like great value. While a points redemption books into the base-level room, I’ve submitted a Suite Night Award for the overwater villa – SNAs have cleared for me every time I’ve used them so far, so I’m keeping my fingers crossed for this one.

In New Zealand, however, is where my loyalty to Marriott ends on this trip. That’s because the entire chain only has a single property in the country: the Four Points by Sheraton Auckland, where I stayed back in February and found to be quite unremarkable. 

Instead, this time, I took advantage of the recent IHG PointBreaks promotion and booked two nights at the Crowne Plaza Auckland for 15,000 IHG Rewards points per night.

I had earned these points from applying for the Chase IHG MasterCard a while back, and had been hoping to use them on a PointBreaks promotion – one of the most generous promotions among any hotel loyalty program, where free nights are available for as little as 5,000 points per night – ever since. 

I’ve never stayed at a Crowne Plaza hotel before, and I know almost nothing about the brand, so I’m very curious about this upcoming stay. I’ll be especially looking out to see what kind of treatment I get as an IHG Platinum member, which is a status level that’s granted to all Chase IHG cardholders. 

Crowne Plaza Auckland

Crowne Plaza Auckland

The chain with the strongest presence in New Zealand, however, would have to be Hilton Honors, and the rest of the trip sees a mixture of Hilton hotels and Airbnb stays in the more remote parts of the country.

The Hilton Queenstown looks very nice, so I snagged a room there for NZ$227 ($195). Then, in Christchurch, I booked the Château on the Park, a DoubleTree by Hilton property, for NZ$189 ($162). 

For both bookings, it seemed like a better deal to pay cash, and earn 54x Hilton Honors points back at the moment thanks to the current triple-points promotion combined with my Amex US Hilton Aspire Card, than to redeem my Hilton Honors points – which I’d rather be saving towards a more aspirational redemption in the future.

The Aspire Card also confers instant Hilton Diamond status, so I’ll be drawing upon my suite upgrade pursuits with Marriott Bonvoy and trying to work the same magic on the Hilton chat associates!

Hilton Queenstown

Hilton Queenstown

Finally, I booked Airbnbs for the nights we’d spend in the New Zealand countryside – a cute one-bedroom house for three nights in Te Anau, and a unique, custom-built studio inside a disassembled airplane sitting on the side of the road in Pukaki, a locale about halfway between Mount Cook and Lake Tekapo that we could use as a base to explore both places for our three nights in the region.

Speaking of which…

The Car Rentals

“Wait, what?” You must be thinking. “Ricky’s actually renting a car to get around from place to place?”

Nope. Jessy’s renting a car, whereas I’m chipping in with my expert navigational skills. 😉

(By the way, I do want to officially declare here that one of my most pressing goals for 2020 is to finally get my full driver’s license, so that I can travel properly in places where driving is the best way to get around. After incurring the wrath of bus drivers in Jordan and now forcing Jessy to shoulder the task of driving on the wrong side of the road on her own, there’s really no excuse anymore.) 

Anyway, since this was the first time I was renting a car, I asked some friends for the best money-saving tips on car rentals, and the universal answer seemed to be to use Autoslash and call it a day. And indeed, we managed to snag a Jeep Wrangler in Maui for four days for US$166, plus a small sedan for a week in the South Island for US$208. It’s quite a bit more affordable than I was expecting!

My total out-of-pocket costs for this trip, per person, came to the following:

  • Aeroplan taxes and fees, YUL–YVR–OGG: $80

  • Hawaiian Airlines, OGG–HNL: $50

  • Alaska Mileage Plan taxes and fees, HNL–CXI–NAN–AKL: $65

  • Air New Zealand, AKL–ZQN: $90

  • Aeroplan taxes and fees, ZQN–CHC–AKL–LAX–YYZ: $40

  • Aeroplan change fees (twice): $150

  • Airbnb in Te Anau, three nights: $233

  • Airbnb in Pukaki, three nights: $192

  • Hilton Queenstown, one night: $195

  • Château on the Park Christchurch, one night: $162

  • Car rental in Maui: $109

  • Car rental in New Zealand: $137

  • Day tour of Milford Sound (cruise & hike): $130

  • New Zealand eTA: $38

  • Total: $1,671


After a couple of hard-working and at times stressful months for both of us, Jessy and I are looking forward to spending some quality time relaxing in the sunshine by the beach, followed by a few weeks hiking around the stunning natural landscapes of New Zealand’s South Island, with a little island-hopping through Kiribati and Fiji thrown in for good measure. 

With a few cute Airbnbs in remote locations and long drives through the glorious southern summer nights, this also promises to be a very different type of trip from the more fast-paced adventures I’ve taken recently, and that kind of variety is always good for an avid traveller’s soul. 

Finally, I do want to say that while I will of course be doing my best to keep up with the content here on Prince of Travel, I also want to actually allow myself to relax a bit along this trip – so let’s say that I’ll be putting in 100% effort instead of my usual 110%.

Over the next few weeks, I’ll continue to catch up on my old trip reports, toss in a few Miles & Points think-pieces, and invite T.J. to chip in with a few of his posts as well, but otherwise I’ll be taking things a little easier to prepare ourselves for a full-speed start to 2020.