What Did You Book? – Return to the magical islands of Hawaii and French Polynesia

Hawaiian Air Upgrade, Waldorf Astoria Maui, Hilton Moorea and Conrad Bora Bora

by Sash & Mohammad
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a collage of a hotel and a beach

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And just like that, December has arrived! In the final instalment of “What Did You Book” for 2023, Sash and Mohammad talk through what they’ve been up to on the travel planning front, detailing their most noteworthy travel bookings over the last month and including any handy tips and tricks along the way.

This month, Sash talks through a trip to Hawaii using Hilton Honors points and flying business class on HawaiianAir, meanwhile, Mohammad plots his return to French Polynesia after a thoroughly memorable trip in the summer of 2023. Read on till the end for an interesting data point for Hilton’s Free Night Certificates.

Sash was determined to avoid flying an economy Air Canada flight back from Maui, Hawaii. He scoured for premium cabin options, and after nearly giving up and accepting his fate in economy, he remembered Mohammad’s intriguing way to fly to Hawaii, and booked Hawaiian Air business class.   Moreover, Sash made a high-value Hilton redemption booking during the peak holiday travel season at the Grand Wailea Waldorf Astoria on Maui.  He share’s his experience on how he put the entire trip together on points and miles.

Meanwhile, having just returned from French Polynesia for the very first time, Mohammad found himself yearning to get back to all the coconut and passion fruit smoothies he’d been enjoying there on the daily, and in the process, hope to explore more of what the French Polynesian islands have to offer, in addition to cringe Instagram moments. Like Sash, Mohammad also leveraged the power of the Hilton program to piece together an itinerary across two properties for the time being.

What did Sash Book?

Grand Wailea, A Waldorf Astoria Resort

Hawaii is like a second home to our family, and we tend not to go more than 24 months without visiting the islands. After we made the decision to return to Maui during the holiday season this year, I was in shock to see the significant increase in hotel costs. Properties like the 4-star Wailea Beach Marriott Resort on Maui have seen over a 2x increase in cost from sub $300 to $700+ per night.  5-star resorts like the Grand Wailea have surged to over $1000/night.  I can tell you that none of the resorts in Hawaii are worth paying this sum of money per night (except perhaps the Four Seasons Lanai).

a large resort with many swimming pools and a beach

Grand Wailea, A Waldorf Astoria Resort, source: travelweekly.com

The solution to offset the high hotel costs is obviously points with the vast array of properties scattered throughout the islands that are part of the Hilton, Marriott, and Hyatt reward programs.  Given that we wanted to spend most of our 11 days on Maui, the Grand Wailea Resort, a Waldorf Astoria property, seemed like a great place to burn my 2 expiring Free Night Certificates (FNC). I have been on the property before, and it looks like a fantastic place to relax with the family with its plethora of amenities. Plus, it has recently undergone a renovation.

a pool with boats and a building with a roof and palm trees

source: travelandliesure.com

I booked 7 nights in total: 2 nights using FNC and 5 nights at 110,000 points/night using Hilton Honors points to take advantage of the free fifth night. Cash rates for my nights were well over USD $1350/night during the holidays.

a screenshot of a hotel room

Total Price: 440,000 Hilton Honor points + 3 FNCs

The cash equivalent price for my dates would have been astronomical. Take a moment and let the power of points and miles settle in for a moment.

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Over the past couple of years, I’ve become a big fan of the Hilton Honors reward program, notably because:

  1. Their Free Night Certificates (FNC) can be used for ANY category property.
  2. We have seen American Express US hand out FNCs like candy over the past couple of years on new Hilton credit card sign-up offers. This was in addition to their high ongoing welcome bonus offers.
  3. Hilton has an almost ongoing sale to purchase their points at a fantastic 0.5 cents/point. It’s often to purchase points to redeem at high-priced properties rather than book outright. In my booking above, rather than pay $1375/night, the same room could be booked for $550/night after purchasing 110,000 points.
  4. It is easy to attain Diamond status by holding a Hilton Aspire American Express credit card

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Hawaiian Air First Class

As everyone knows, finding “cheap” flights during the holidays is difficult. Finding business class, lie-flat seats to/from Hawaii at a reasonable price is even more difficult, especially on the nonstop routes to/from the East Coast. United and Hawaiian Air are the only airlines that offer lie-flat options for the long-haul route, but award availability for a family is exceptionally scarce.

a map of the united states

Hawaiian Air Lie-Flat First Class, routes to mainland US. Created using flightconnections.com

If you have flown back to the mainland from Hawaii, then you know that most flights are a red-eye. Until a month ago, I was booked in Air Canada Economy on their B787 direct from Honolulu to Toronto, a nearly 9-hour journey. I could not accept this fate of mine and decided to give it another go in my quest for a premium cabin.

Mohammad had written a great post on how to fly Hawaiian Air Business Class (marketed as First Class) at a reasonable price point. The idea he presented was to purchase an economy class ticket and upgrade using HawaiianMiles. What’s great about Hawaiian Air is that every fare class is upgradeable, except basic economy. Plus, refundable fares only cost about 25% more, which is great for people like me who love having flexibility.

a screenshot of a website

Hawaiian Air Pricing Example

Prior to booking the ticket, I first used ExpertFlyer to confirm upgrade availability for the Honolulu – New York (JFK) route on the day I wanted. It was available, but only in Flex, which cost 50,000 HawaiianMiles versus only 25,000 had Saver been available.

a screenshot of a computer

ExperFlyer – Hawaiian Air Upgrade Availability Example (4 Flex, 0 Saver)

I paid USD 868/person for a refundable fare and applied 50,000 HawaiianMiles, transferred from US American Express Membership rewards at a 1:1 rate. In addition, I was refunded 70,000 Aeroplan points/person for cancelling my economy ticket, which offset the upgrade cost.  Although USD 800 may still seem like a lot of money, I have seen ticket prices as low as $250 during non-peak travel periods, an excellent value!

What did Mohammad Book?

French Polynesia was a dream. My wife and I had such an incredible time during this past summer as we visited Bora Bora alongside one night in Tahiti. As you would expect, the islands, lagoons and pristine waters were breathtaking – but there was just so much more that I found appealing. The culture, the influences, the history of the various groups of islands – all added such a fascinating layer to the trip – something that looking back I found was sorely missing from an otherwise memorable experience in the Maldives.

a mountain with palm trees and a cloudy sky

The Island of Raiatea

French Polynesia is made up of over 120 islands and atolls and split into roughly 5 groups of islands (Society Islands, Tuamotu, Gambier, Marquesas and the Austral Islands) which together span a distance roughly the size of continental Europe. Probably the three islands that most often might come to mind when talking about French Polynesia as a tourist destination would be Bora Bora, Tahiti and Moorea, all of which are part of the Society Islands (the Leeward Islands specifically), and it’s these three islands where Hilton’s footprint lies. Tahiti and Moorea each have a Hilton property, whilst Bora Bora hosts a Conrad.

a screenshot of a hotel

Hilton footprint, French Polynesia

I recall when leaving Bora Bora, I just had an instant interest in returning in the near future, and whilst I’d be more than happy to re-visit the island for some R&R, I wanted to ideally tack on another 1-2 islands at least in order to get a better feel of the less touristy islands. Something like Taha’a (also known as the Vanilla Island as it accounts for over 80% of the FP’s vanilla production) or Moorea would be a start as both islands have decent hotel options to begin with and if possible, try and hit a few others that had piqued my interest such as Rangiroa, Fakarava, Huahine or Raiatea to name a few.

an aerial view of an island


So how has points availability been historically for the Hilton properties?

  • Conrad Bora Bora: Standard room rewards cost 120,000 Hilton Honors points, which is currently the higher end of reward rates at Hilton properties (with the exception of the 150,000/night Waldorf Astoria Los Cabos and Maldives). The property tends to open space up close in and also does some big award drops 1-2 times a year across most of the calendar. You’d typically need to act fast on these award drops as award space goes quick once word gets out on the blogosphere. Note: A standard room at the Conrad is a suite, not a villa.
  • Hilton Moorea: Post-Covid, this Hilton has been surprisingly stingy with award space. Often you can go through the entire calendar without finding more than a solitary night available to book on points. When available, a standard room can be booked for 95,000 Hilton Honors points.
  • Hilton Tahiti: Located in close proximity to Papeete Airport, I had expected this to be a run of the mill airport hotel, but in fact was quite a decent resort all things considered – a great way to comfortably kill a night or two as you recover from/ wait to depart on a long haul flight. For our stay we had booked cash rates, however standard reward pricing is 80,000 Hilton points and availability is generally easy enough to come by.

Toying with the idea of returning to French Polynesia in 2024, I knew that a third island outside of Bora Bora and Tahiti would need to be a part of my plans, though with the arrival of our little third wheel, I knew I couldn’t get too adventurous in going for basic lodging in one of the more remote islands that I had originally pined for. As such, Moorea was definitely on the radar as the island seemed to be a great destination in and of itself without taking into account the hotel we’d stay at, or perhaps Taha’a which has a Relais & Chateaux property on the island.

a building with a sign and a sign on it

Fortunately while doing some casual browsing in late October, I had noticed a big drop of award space at the Conrad that had gone under the radar, showing almost every day available between Jan-August. I went ahead and speculatively booked a pair of rooms for March spring break at the Conrad for a low probability trip with some family. It wasn’t until recently, when I went to cancel these bookings (timing didn’t end up working), that I started looking at the calendar again. Conrad availability had now dwindled to a handful of days post-February however to my surprise Hilton Moorea was now showing pockets of availability post-August, with a generous smattering in November in particular.

Given how rarely I had seen space available here, I went ahead and quickly booked 2x 3-night stays in different weeks in November and also set up some alerts for the adjoining days for the Conrad Bora Bora using my subscriptions to Awayz and MaxMyPoints. The three night bookings each costs 285,000 Hiltons points each (95,000/night) which otherwise were coming in at ~USD 2,300+.

a screenshot of a hotel

As luck would have it, the very next morning my alerts went off as the Conrad Bora Bora released award space for the entire month of November 2024. Having been burned a few too many times in the past for waiting too long, I quickly went to work to nail down dates that would work alongside my existing Moorea bookings. I ended up booking 5 nights at the Conrad entirely on points to take advantage of the 5th night free benefit, which ended up costing 480,000 Hilton points (120,000 points/nt; 5th night free) for a booking that would otherwise have cost USD $8,200+ at the least expensive rate.

a close-up of a hotel reservation

Conrad Bora Bora, 5 night booking

To thread the needle a bit more; and seeing as I had no flights booked as of this time, I wanted to give myself a little added flexibility for when I look to book my flights. To do this I had sandwiched my Conrad stay between the two sets of Moorea stays, and added a further night in Moorea. My current bookings as things stand is as follows:

  • Hilton Moorea 3 nights (points)
  • Hilton Moorea 1 night (Free Night Certificate)
  • Conrad Bora Bora 5 nights (points)
  • Hilton Moorea 3 nights (points)

Ideally I’ll look to stay my first three nights at Moorea followed by the Conrad, meaning I’d be dropping the last 3 nights at Moorea pending any unforeseen complications with flight scheduling along with 1 night upfront at Moorea. This also means that If I’m able to line up flights correctly, I’d still have the option to add on a third island for 2-4 days at the tail-end of my trip. Thankfully though, I have plenty of time to work on that now that the backbone of my trip is sorted, and I’ll jump right on that once I have more visibility on my outbound flight.

Some may noticed that I’ve squeezed in a solitary Free Night Certificate redemption at the Hilton Moorea into the mix. Primary reason for this was to maintain some flexibility at the beginning of the trip. Since I used points for the first booking, I’d be able to make changes prior to 7 days of the stay beginning – meaning if I shortened it by a day, I’d be able to get my points refunded back. Had my first night been a Free Night Award, I could have run the risk of having the certificate refunded back to me without a lot of time left to use it – hence I used it to redeem a night I was more certain that I would use.

Whilst points bookings can be done online, to redeem one of Hilton’s Free Night Award’s (“FNA’s”), you are required to call into their phone line. With my stay commencing in mid-November, and an additional 5 FNA’s sitting in my wife’s account, I really wanted to try my luck on using at least one of the two FNA’s in my account towards the one night booking. Unfortunately the certificates both expire prior to the trip – Aug 30 and Oct 5th.  Anecdotally and in speaking to others, I have regularly read about successful instances of Hilton agents able to extend certificates by 2-3 weeks in order to use towards a booking. Once in a while, I’d hear an instance of 4 weeks, and only about twice have I heard of an extension for as long as 6 weeks (with it happening to Sash once).

Given the above – I was pessimistic of my chances as even the Oct 5th expiring certificate would need an extension of 6-7 weeks. Fortunately the agent I was connected to was an utter delight. I had politely explained my ask to her and made it clear that I would understand if they couldn’t, but I had to ask – and without flinching she suggested extending the Aug FNA to Dec 31 and then went about doing exactly that and successfully completing the booking. While I don’t expect to get this lucky any time soon, it is at least heartening to know that there is no hard system limit on Hilton’s side that prevents FNA’s from being extended past a few weeks. I hope the key takeaway here is not that you should act like an entitled you-know-what the next time you call Hilton to ask for an FNA extension, but rather that there is never any harm in asking!

Final Word

As 2023 winds down to an end, our plans for 2024 are cranking up. Clearly winter is about to hit the nation’s capital as it has both of us dreaming of island paradises and warmer weather elsewhere. Hope you enjoyed reading along this month’s double dose of Hilton points alongside the refresher on one of the best uses of Hawaiian Miles. As always please feel free to leave you questions, comments and/or feedback below! Thanks for reading along and we look forward to being back in 2024!

a hut on a dock in the water with mountains in the background

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