After years and years of accumulating points with one eye on this specific prize, it’s finally time to check a major heavyweight off the aspirational travel bucket list: a trip to the clear-blue waters and overwater villas of the Maldives, with a series of premium flights worthy of the occasion on the way there and back. 

The Outbound

Back when I had booked the Cathay Pacific First Class fares on New Year’s Eve 2018, I had scheduled the outbound segments (from Hanoi to Vancouver, via Hong Kong) for July 2019, followed by the return segments in October 2019.

At the time, Jessy and I planned on being in Asia in the summer of 2019 anyway, and would then need to make it to Vancouver for a friend’s wedding, so the outbound flights made perfect sense, and eventually served as the conclusion to a very memorable summer trip to Japan, China, and Cambodia. 

The return segments in October, however, were built around a more nebulous set of plans to visit the Philippines sometime around then, which didn’t end up materializing. I therefore needed to reschedule the return flights for sometime in the future, and this Maldives trip in the spring of 2020 seemed like the ideal use for it.

As a general rule across paid and award travel, if travel has not yet commenced on an itinerary, then you may change the ticket to travel within one year of the original ticketing date (subject to a change fee and/or fare difference); however, once travel has commenced, you may change the remaining segments to travel within one year of the first flight on the itinerary.

Therefore, after I had flown the outbound in July 2020, I called Cathay Pacific to push the return segment to March of this year. Given that this was a very low fare in the first place, and that I had paid US$988 for a First Class ticket that’s normally US$15,000+, I was half-expecting to be quoted an obscene fare difference.

However, to my surprise, Cathay Pacific indeed honoured the generous fare rules on this First Class fare in spite of the erroneous original price, allowing me to change not only the date but also the departure airport from Vancouver to New York JFK! 

I therefore ended up with a ticket that goes from New York JFK to Hong Kong in Cathay Pacific First Class for only an additional US$150 or so in change fees and fare difference, which would become the backbone of my outbound journey to the Maldives.

I’m looking forward to see how the Cathay First product is holding up compared to my incredible maiden flight and a slightly less impressive showing the second time, especially after the airline recently refreshed their First Class soft product with new service and amenity concepts.

The plan was to head directly from Hong Kong to the Maldives, although a series of coronavirus-induced airline cancellations meant that I had to change plans several times.

In the end, after my originally booked AirAsia flights via Kuala Lumpur were axed, I elected to redeem 50,000 Aeroplan miles per person – from Asia 1 to the Indian Subcontinent – for a much smoother journey on Singapore Airlines business class on the 777 and the 787.

That’s arguably not an ideal use of Aeroplan miles for what amounts to a couple of regional flights, but I do feel much better about the back-to-back four-hour flights on the ever-reliable Singapore Airlines business class than if I were sitting in AirAsia, which would’ve been a bit of a buzzkill in the middle of a trip that’s meant to be heavy on the luxury factor.

Finally, I simply needed to take care of the short flight from Montreal to New York, so I redeemed a handful of 10,000 CIBC Aventura points per person for the quick hop across the border in Air Canada economy class.

The Return

I’ve been on a bit of a mission over the past year or so to fly as many of the world’s best airline products as possible, striking off a few major names like Emirates First Class (old and new), ANA 777 new business class, and Qatar Airways Qsuites in the process. 

Well, one of the big-hitters that’s still on my list is the Etihad Airways A380 First Class Apartments, so it’s finally time to take care of this one.

I booked a journey of Malé–Abu Dhabi–London in First Class for 62,500 American AAdvantage miles per person, which will also allow me to sample the airline’s smaller, but no less glamorous, First Class product on the Boeing 787 on the Malé–Abu Dhabi leg as well. 

American AAdvantage miles are among the best currencies for booking Etihad flights, since they do not levy any fuel surcharges and have reasonable (but not outstanding) award rates. 

Indeed, I’d consider the “Europe to Indian Subcontinent” price point of 62,500 miles in First Class to be one of the better sweet spots in the award chart, which made me feel better about the fact that I could only book the London route for eight hours on the Apartments, rather than the New York JFK route for nearly 15 hours, due to a lack of availability on the latter. 

However, the major challenge for me in this scenario was that I hadn’t collected any meaningful amounts of AAdvantage miles (in hindsight, it was probably a good thing that I didn’t jump on that “grAAvy train” in the US), so I was forced to go through the rather sub-optimal methods of transferring miles into AAdvantage that we have in Canada to earn the 125,000 miles required for this booking.

I converted a stash of RBC Avion points over to AAdvantage during a 20% bonus event on top of the usual 1:0.7 ratio, which earned me about half of that amount. Then, rather painfully, I topped up the remainder with Marriott Bonvoy points at a 3:1 ratio, and thankfully I was able to secure my booking with AAdvantage’s generous five-day award hold policy while I waited for the points to post.

This is definitely one of the more resource-intensive trips that I’ve booked in recent times, so it’s safe to say that, on an eight-hour overnight flight in the Apartments when the majority of passengers might choose to sleep, I will instead be resolutely eating, drinking, showering, and lounging up a storm to make the most of the occasion.

Etihad drops us off in London, and from there I still needed to make my way back to Montreal.

Presumably, I’d be in a state of considerable exhaustion by this point after the Apartments, and given that Jessy needed to be home on a tight schedule, there was no better way to cross the Atlantic than an entirely unassuming flight on Air Canada business class, where I could catch up on sleep the entire time without feeling like I’m missing out on anything.

As before, I enlisted the help of a friend with Air Canada Super Elite status to get this booking completed for 55,000 Aeroplan miles per person and minimal fuel surcharges, although I did have to pay the UK Air Passenger Duty of about $300 per person on account of our London departure. This wasn’t a fun cost to swallow, but it was definitely one of those times when the convenience outweighed the cost.

The Air Canada 777 would bring us to Toronto at 3pm local time, and since there was only one seat on the 6pm flight back to Montreal, I put Jessy on that one, before booking myself on the midnight departure, giving myself some time to wrap up the trip with an impromptu round of Miles & Pints in Downtown Toronto hosted by the local community. 

In the end, my overall routing looks as follows: 

• Montreal to New York LaGuardia on Air Canada, departing 8:45am and arriving 10:16am, economy class

• New York JFK to Hong Kong on Cathay Pacific, departing 12:45am and arriving 5:40am, First Class

• Hong Kong to Singapore on Singapore Airlines, departing 3:45pm and arriving 7:45pm, business class

• Singapore to Malé on Singapore Airlines, departing 8:35pm and arriving 10:10pm, business class

• Malé to Abu Dhabi on Etihad Airways, departing 8:30pm and arriving 11:45pm, First Class

• Abu Dhabi to London Heathrow on Etihad Airways, departing 2:40am and arriving 6:40am, First Class

• London Heathrow to Toronto on Air Canada, departing 12pm and arriving 2:25pm, business class

• Toronto to Montreal on Air Canada, departing 12:30am and arriving 1:49am, business class

The Hotels

Sandwiched between two whirlwind itineraries is the actual objective of the trip itself: the Maldives and their stunning overwater villas.

It’s one of those high-end bucket-list destinations that most travellers outside the Miles & Points community would only dream of, but of course, having access to the right points currencies unlocks many of these spectacular resorts at a fraction of their usual cost.

All of the Maldives resorts look downright gorgeous, so while I did spend lots of time poring over which particular resort I’d like to visit, I also felt pretty casual about the whole thing from a broader perspective, since I was sure that whichever resort I chose would be extremely memorable and would still leave me a wealth of other places to try out next time.

The St. Regis, the W, the Westin, the Conrad, and the Waldorf Astoria are all fantastic options, but in the end I settled on the newly-opened JW Marriott Maldives for 340,000 Marriott Bonvoy points – 85,000 points per night for four nights, with a Fifth Night Free. 

While the St. Regis and the Waldorf both look incredible as well, ultimately I’m a very loyal person, and I just couldn’t resist sampling my favourite JW Marriott brand at a brand-new property in such a unique and memorable location. 

The JW Marriott also offers the benefit of allowing you to redeem points directly for an Sunrise Overwater Villa as the base room, instead of booking a lower-category Garden Villa with points and hoping for a space-available upgrade – even with my suite-talking tactics, I didn’t want to leave this one up to chance, since the overwater villas are the biggest reason why you’d go to the Maldives in the first place. 

Nevertheless, even though redeeming points is a smoking-hot deal at any of these properties where the room rates regularly exceed US$1,000+/night, I’m under no illusions that this will be a cheap getaway by any means. Most of the resorts in the Maldives charge an obscene amount for the seaplane or speedboat transfers from Malé International Airport, and the JW Marriott Maldives is no exception with a mandatory seaplane transfer of US$695 per person. 

On top of that, the food & beverage costs at the resort are going to be quite eye-watering to say the least, and as much as Jessy and I would consider ourselves masters of jam-packing our bags with snacks and instant noodles in the face of predatory pricing, there’s no denying that we’ll also want to splurge a little on dinner and drinks as well, given our magnificent surroundings.

The final hotel folio is going to take some digesting, that’s for sure, and I think anyone visiting one of these resorts needs to have the right expectations going in. At the very least, I look forward to deciding properly for myself whether it’s all worth the hype!

In addition to the main attraction in the Maldives, I also needed one night in New York before catching my Cathay Pacific First Class flight (it was originally two nights, and I had planned to check out the TWA Hotel JFK on the second night, but a coronavirus-induced schedule change put me on an earlier Cathay departure and scuppered those plans.)

Jessy and I decided we’d rather spend time in Brooklyn during our short visit this time instead of going into the city, and I decided – somewhat on a whim – to skip over the usual chain hotels and try something different.

We booked The William Vale, an artful boutique hotel at the northern end of Brooklyn, for one night using a Virtuoso rate of US$255, entitling us to a room upgrade, early check-in and late checkout, breakfast for two, and a US$100 food and beverage credit, which should definitely kick off the trip on the right note. 

Am I Worried About the Coronavirus?

I must say that the COVID-19 outbreak – especially as the daily number of global new cases begins to exceed that of within China – has put a slight damper on my excitement for this trip, and I’ve put some serious thought into whether or not to call off the whole thing.

In the end, I decided to proceed cautiously, although I’m of course keeping an eye on the rapidly developing situation and ready to change plans at a moment’s notice if necessary. 

Obviously, everyone’s risk tolerance is different for this kind of stuff, and I would’ve felt differently if we were travelling to a region where the outbreak was spiralling out of control. On this trip, though, equipped with our N95 masks and a rigorous hand-washing regimen, I don’t see enough of a threat in the destinations on the agenda to call off the trip entirely. 

It’s similar to my Chinese New Year trip back home earlier this year: I took off for Beijing on January 22, just before the Wuhan lockdown was announced, thinking at the time that things wouldn’t be too abnormal for myself and my family in Beijing. Once it became apparent that the spread within China was taking on a whole new order of magnitude, though, I changed course and cut short my visit early on very little notice. 

The nature of award travel is that it gives us an added level of flexibility that’s mostly unavailable on cash tickets, so while I’m hopeful that I won’t need to make any such adjustments on this trip, I feel well-prepared to do so if the rapidly changing situation does indeed call for it. 

I’d recommend the same course of action for anyone who’s on the road during these tempestuous times: exercise caution, practice good health and cleanliness habits, and be prepared to change things up on short notice (and even enter into quarantine) if necessary. 

Conclusion

The Maldives – wow. After only ever dreaming about visiting a resort like this since I was a young boy, I can hardly believe that it’s finally happening, with another flight on Cathay Pacific First Class (my third overall) and a maiden journey onboard the famous Etihad Apartments only ratcheting up the excitement even further. 

As many of you know, I’m generally hesitant to label anything as “once-in-a-lifetime”, but a trip like this, with such a significant cost in both money and points, is definitely one to be savoured in the moment and looked back on with fondness over the next few years. 

I’m keeping my fingers regularly washed and tightly crossed for no coronavirus-induced trip interruptions, and I look forward to sharing the impressions and reviews from this luxury-laden circumnavigation when the time comes.