The Hardest Destinations for Travelling on Points

A while back, I wrote an article on “The Easiest Destinations for Travelling on Points”, which outlined some of the best destinations around the world where your airline miles and hotel rewards points will fetch the greatest value.

In this article, let’s follow-up with the other side of the discussion: which destinations are the most challenging to “do on points”? Compared to the “easy” destinations like Asia and the Middle East, what are the places around the world where you’d have to work a fair bit harder to book your dream trip on points?

1. Hawaii

This might be surprising, or even a bit controversial, but I’d argue that Hawaii is very much one of the more challenging places in the world for maximizing the value of your points.

Now, there are plenty of options for booking travel to Hawaii while leveraging loyalty programs, and some of them may even look like very attractive sweet spots on paper.

Take, for example, the ability to book Vancouver–Hawaii flights for only 12,500 or 25,000 Aeroplan points in economy or business class, respectively, which might strike you as an awesome sweet spot given that it falls just under the 2,750-mile distance threshold.

The problem lies in Hawaii’s sheer popularity among North American travellers. Any sweet spots that exist on paper are very much hotly contested, and you’d be hard-pressed to find Air Canada business class seats that are actually bookable in the region of 12,500 or 25,000 points one-way under the dynamic pricing model (not to mention a similarly low-priced seat on the direct Dreamliner services from the East Coast).

You’ll encounter the same challenges on the hotel side: Hawaii is home to lots of properties with the major chains, but they’re invariably priced extremely expensively, both in points and cash.

For example, I was genuinely shocked when the Wailea Beach Marriott Resort Maui went from a Category 6 to a Category 7, because even the Category 6 designation when I had stayed there felt far too high compared to, say, amazing Category 5 resorts in South East Asia.

Wailea Beach Marriott Resort Maui

At the end of the day, the major hotel chains know that they can charge a huge premium for their Hawaii resorts. There’s always a steady supply of travellers from the North American mainland who are looking for an “easy” beach vacation in which they don’t need to bother with long flights and language barriers, and who are more than willing to pay the US$500+/night cash rates for everything that Hawaii has to offer.

That same reasoning also plays into the downright poor elite treatment that you’ll often encounter at Hawaii resorts.

As a Titanium member at the Wailea Beach Marriott Resort Maui, my breakfast benefit was limited to a pastry, fruit cup, and coffee from Starbucks – all while the hotel wanted to charge a US$35/night resort fee for the privilege of using beach chairs!

“Elite breakfast benefit” at the Wailea Beach Marriott Resort Maui

Don’t get me wrong, I liked Maui – but far more for its whale-watching and spectacular sunsets, than for any good value I was able to get out of my points.

My advice? Use Air Canada’s eUpgrades to snag business class en route to Hawaii. Then, consider renting a villa or Airbnb when you’re there and saving your hard-earned hotel points and free night certificates for places where they’ll go a lot further.

2. South America

If you think back to our discussion on the “easiest” destinations to book on points, you might recall that they’re generally arranged along a rough round-the-world path within the northern hemisphere, with a slight dip below the equator into South East Asia.

The more challenging parts of the world for extracting value from your points, then, largely lie in the southern hemisphere – all for slightly different reasons, starting with South America.

From a North American perspective, the biggest hindrance to an “amazing points trip” in the traditional sense is a lack of high-quality airline products that serve the trans-Americas market.

Copa Airlines 737 business class

After all, if you’re headed to Europe or Asia, or indeed Africa or Australia, you could choose among many of the world’s leading airlines to get you there.

But flying down to the Americas leaves you with rather slim pickings, as you essentially have two options at your disposal, neither of which are necessarily ideal:

  • You could aim for a simple and convenient direct journey on Air Canada, United, or American business class, although it can often be tough to find well-priced award availability.
  • Alternatively, you could choose a more interesting routing on Copa Airlines or Avianca, perhaps with a stopover in Panama or Colombia along the way; however, both of these airlines’ onboard products are average at best.

But on the bright side, flights between different South American countries are often disproportionately expensive, making it a great deal to redeem points for intra-continental hops (especially with Aeroplan categorizing all of South America as a single zone).

(I’d note that a few regions of the continent – say, Patagonia – are still somewhat lacking in terms of flights that we can easily book on points. Perhaps an area for a future Aeroplan airline partner to address?)

There are also many decent hotel redemptions to pick from, even if the quality isn’t going to blow you away like South East Asia or the Middle East – such as Tambo del Inka in Cuzco, the Park Hyatt Buenos Aires, or the JW Marriott Rio de Janeiro just to name a few.

Rio de Janeiro, Brazil

Overall, South America has plenty going for it in terms of maximizing your points, with the major caveat that the northbound and southbound flights don’t quite give you the same aspirational fruits of labour as other parts of the world.

Then again, whether you decide to maximize your sleep on a direct overnight flight and hit the ground running the next day, or to break up the journey and see more of the Hispanosphere in Panama or Colombia, I think it’s fair to say that both options can only add to, rather than detract from, the overall experience of a South America trip.

3. South Africa & Sub-Saharan Africa

Similar to South America, I’d categorize Sub-Saharan Africa as a region where award travel tends to be of at least a moderately, if not quite overwhelmingly, difficult. And as one of the most popular and well-served destinations within this region, South Africa will be a natural focus for much of the discussion.

There’s often the same trade-off between availability and quality that we encountered back in South America: airlines like Swiss, Lufthansa, Turkish Airlines, and Singapore Airlines will offer a better onboard product but will be trickier to book, whereas Egyptair and Ethiopian Airlines tend to have ample availability and a convenient routing at the expense of the aspirational touch.

Ethiopian Airlines 787 business class

(The recent financial troubles of South African Airways also removed a potentially useful option for flying to their home country, including some very interesting links for round-the-world travel in the form of their southern transoceanic routes to São Paulo and Perth.)

Once you look outside of South Africa and towards any other Sub-Saharan African country, the flight options continue to dwindle in number, with Ethiopian Airlines essentially acting as a mainline carrier for the entire region.

There are a handful of fifth-freedom routes by TAP Air Portugal, Brussels Airlines, or Turkish Airlines that you could book using Aeroplan short-haul awards, but these are the exception rather than the norm.

Then, there’s also the frustration that the entire Atlantic zone is fairly expensive under the new Aeroplan program – you can expect to pay 85,000–100,000 Aeroplan points for a one-way business class flight on most journeys to a Sub-Saharan African destination from an North American origin.

If you’re headed to this part of the world, there are a few Oneworld sweet spots worth paying attention to instead, such as 70,000 Alaska miles for Cathay Pacific First Class and business class to South Africa or 75,000 AAdvantage miles for Qatar Airways Qsuites via Doha.

Hotel redemptions are another redeeming factor: Sub-Saharan Africa is peppered with low-category hotels across most of the major chains, which nevertheless continue to charge “Western tourist” prices if you were to pay with cash.

Marriott Accra

Therefore, you should be able to find good value in your hotel loyalty points wherever you go, whether that’s in one of the national capitals or on the doorstep of a desert safari – although you should still expect to pay top dollar for Africa’s “true” luxury safari experiences.

That brings me to a final consideration: the travel costs other than your flight and hotel tend to be pretty significant in Africa, too.

This isn’t Paris or Bangkok, where you can roll into town for a week and spend every minute exploring a new part of town. Instead, much of what Africa has to offer lies beyond its metropolitan areas, waiting to be discovered with the help of organized tours and knowledgeable guides – often at a significant expense.

That’s one more factor to consider if your primary goal with Miles & Points is to book a memorable trip with minimal out-of-pocket spending.

4. Australia & New Zealand

Finally, I’d consider Oceania to be the most challenging part of the world to visit on points. It’s by no means impossible, but to make it happen, there are quite a few ducks that you’d need to get in a row.

In particular, the real ugly duckling is flight availability, which has historically been quite difficult to track down in this far-flung, yet very popular corner of the globe. 

Outside of the current inflated prices due to Australia and New Zealand’s border restrictions, it’s possible to snag reasonably priced direct transpacific Air Canada business class flights from Vancouver to Sydney, Melbourne, Brisbane, or Auckland – but it would require booking for the very end of the schedule about a year in advance. 

It’s no different for partner airlines. United business class awards from the West Coast to Australia are very much a rare occurrence.

Air New Zealand is notorious for being among the stingiest airlines in all of Star Alliance in terms of releasing any economy or business awards. If you see a transpacific Air New Zealand business class award, book it now and ask questions later. 

Air New Zealand business class

As for Fiji Airways with Alaska miles? It’s a solid sweet spot on paper at 55,000 Alaska miles for a one-way business class journey with a stopover in Fiji, but in practice, you’d be very lucky to find business class awards on the Los Angeles or San Francisco routes.

The reality is that the vast majority of Oceania-bound travellers who want to fly on points will need to route through Asia or the Middle East one way or another.

Here, availability has traditionally been a little easier to find between ANA, Asiana, Air China, Cathay Pacific, Etihad Airways, Singapore Airlines, and Thai Airways – especially if you’re willing to fly into a smaller market like Brisbane or Perth and then hop around on Qantas or Virgin Australia awards. And on the plus side, you’ve got a wider range of world-class airlines to choose from as well. 

But having said that, connecting through Asia means that you’re looking at a 24-hour journey from North America, so you might well be tempted to break things up with a stopover in Asia – which would then introduce a whole other dimension into your trip. You can see how booking a trip to Australia or New Zealand on points can get very complex very quickly.

Looking at accommodations, I feel that higher-end hotels in Australia and New Zealand are fairly comparable to Canada in terms of their quality and price point – that is to say, not necessarily the best value, though with the occasional sweet spot like the Westin Perth or Hilton Queenstown

Hilton Queenstown

In the big picture, when you combine the geographic isolation of Australia and New Zealand with their popularity among North American travellers as friendly English-speaking upside-down countries, you end up with a significant challenge if you’re looking to book a trip on points.

A bit of advance planning – which should be very feasible these days, give that it’ll be a while until these countries reopen their borders – can go a very long way. 


Some places around the world get the short end of the stick when it comes to award travel sweet spots, whether they’re a bit too close to home (like Hawaii) or a bit too far away (like various parts of the southern hemisphere). 

Travellers to these regions must deal with a narrower selection of airlines, hard-fought battles for award availability, and – in the case of Hawaii, and to some extent the rest of North America too – a miserable level of elite treatment that’ll make you wonder what on earth your Edmonton mattress runs were all for. 

But don’t forget: we’ve talked about the places around the world where it’s relatively easier and harder to extract value out of your points – yet, at the end of the day, the true “value” of a trip is subjective to you as an individual traveller.

If South Africa and Oceania are the places that tug at your heartstrings, then that’s where your points will go furthest for you in spite of the challenges along the way; there’s no point visiting Dubai’s desert resorts or East Asian metropolises instead just because they might fetch value on paper more easily. 

  1. Dilan

    I don’t know if it’s been discussed before but for South America a good deal is flying Europe to South America with a stopover in Canada as latitude fares usually price around 50,000 points so if you have any eupgrade credits to spare you can get a pretty good deal. You just have to stay under the 7,000 mile distance for example AMS-YYZ-BOG

    1. Ricky YVR

      Thanks for the tip. As Josh mentioned, the inability to add a stopover in Canada is fairly limiting to this sweet spot – though I imagine that was the intention.

    2. Josh YVR

      If only Aeroplan would allow Canada/US stopovers on flights with an international origin and destination 😤

  2. JL

    What about Bora Bora?
    I find it pretty tough to get there with points in premium cabins and with reasonable flight schedules.

    1. CR

      YVR-SFO-PPT seems to continue being coded as tier 2 on the NA-Pacific chart (should be tier 1)

    2. Jay*

      You just have to diversify into programs that are much more accessible via the US market and it isn’t too bad. 🙂

  3. Archie

    Hey Ricky! Do you think Central Asia would make an honorary mention to this list?

    1. Ricky YVR

      Turkish Airlines’s comprehensive coverage in the region, as well as good availability, is the saving grace. But the price points aren’t the cheapest, and the eastbound connections are also quite sparse (Air Canada and Asiana come to mind, but that’s about it), so yes I think an honorary mention would be fair.

  4. Oz

    Ricky you are such a trail blazer. If you have a top 5 good times list I would like to follow. So far I’m planning to follow Amy Disney formula. Maybe you should too! Hang out at the stroller park anytime soon?

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