In contrast to the easiest destinations for travelling on points, some parts of the world are much more difficult to book with points. This could be due to geographic location, popularity, a lack of award availability, or a host of other factors.

Compared to the “easy” destinations like Asia, Europe, and the Middle East, what are some 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 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.

For example, using Aeroplan points, it’s theoretically possible to book Vancouver–Hawaii flights for as few as 12,500 or 25,000 Aeroplan points in economy or business class, respectively, which might strike you as an awesome sweet spot.

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  25,000 points one-way under Aeroplan’s dynamic pricing model for Air Canada flights (not to mention a similarly low-priced seat on the non-stop Dreamliner services from the Eastern Canada).

Rather, you can expect to pay much more for these flights with dynamic pricing, especially during peak season.

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. This is especially true during busy travel periods, as prices can go through the roof.

For example, the Courtyard by Marriott Oahu North Shore has prices that range from 58,000–73,000 Marriott Bonvoy points per night over the summer months. In many other parts of the world, that same number of points will get you a much nicer hotel.

At the end of the day, the major hotel chains know that they can charge a huge premium for their Hawaii resorts. After all, 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 $500+/night cash rates for everything that Hawaii has to offer.

That same reasoning also plays into the reduced elite treatment that you’ll often encounter at North American hotels (including Hawaii), especially when compared to other parts of the world.

For example, as a Titanium member at the Wailea Beach Marriott Resort Maui, you might be surprised to learn that your complimentary breakfast is limited to a pastry, fruit cup, and coffee from Starbucks – all while the hotel charges a $35/night resort fee for the privilege of using beach chairs!

Maui is a great place for whale watching and spectacular sunsets, but perhaps not for outstanding value from points redemptions or great elite treatment.

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 premium-quality airline products that serve the trans-Americas market.

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 solid options at your disposal:

• You could aim for a simple and convenient direct journey on Air Canada, United, or American Airlines 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 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. Keep an eye out for many of the fifth-freedom flights within South America.

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 near Cusco, the Park Hyatt Buenos Aires, or the JW Marriott Rio de Janeiro just to name a few.

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 non-stop 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, 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, Sub-Saharan Africa is 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 you might encounter with travelling to South America: airlines like Swiss, Etihad Airways, Lufthansa, Qatar Airways, Turkish Airlines, and Singapore Airlines offer a better onboard product, but can be trickier to book with points due to competition, whereas EgyptAir and Ethiopian Airlines tend to have ample availability and a convenient routing at the expense of the aspirational touch.

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 issue of cost. With Aeroplan, you can expect to pay 90,000–110,000 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 75,000 American Airlines AAdvantage miles or 95,000 Avios for Qatar Airways Qsuites via Doha.

Hotel redemptions are another redeeming factor: Sub-Saharan Africa is peppered with low-priced hotels across most of the major chains, which sometimes charge higher prices if you were to pay with cash.

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 most of Africa’s “true” luxury safari experiences.

Of course, the JW Marriott Masai Mara is an exception to this rule, and a stay here represents one of the best uses of Marriott Bonvoy points, complete with all-inclusive dining, safaris, and more.

That brings us 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. Consider using secondary fixed-value points currencies, such as CIBC Aventura Points, Scotiabank Scene+ points, TD Rewards Points, or BMO Rewards points to offset these costs.

4. Oceania

Finally, Oceania remains one of the most challenging parts 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 first.

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.

In theory, it’s possible to snag reasonably priced non-stop transpacific Air Canada business class flights from Vancouver to Sydney, Brisbane, or Auckland – but it usually requires booking at the last minute, sometimes even within a few days of departure.

It’s no different for partner airlines. United Polaris business class awards from the West Coast to Australia are very much a rare occurrence, and you’re most likely to encounter award space within a week or two of departure.

If you’d like to visit French Polynesia, be sure to keep an eye out for flights via San Francisco with United. While the availability typically doesn’t get released until close to departure, you might be able to score a seat in business class for just 55,000 Aeroplan points.

Air New Zealand is notorious for being among the most restrictive 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.

As for Fiji Airways with Alaska miles, it’s a solid sweet spot on paper at 75,000 Alaska miles for a one-way business class journey with a stopover in Fiji. However, in practice, you’d be very lucky to find business class awards on the Los Angeles, San Francisco, or Vancouver 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. However, you’re likely to contend with the same award availability issues, as transpacific award flights in premium cabins are harder to come by than ever before.

If you can snag some award seats, you’ll also enjoy some of the better airlines out there to make the trip very comfortable when you’re taking the long way to get there. Keep an eye out for flights with ANA, Emirates, Etihad Airways, Qatar Airways, and Singapore Airlines, and also consider flying into a smaller market like Brisbane or Perth and then hop around on Qantas or Virgin Australia awards, which are very easy to come by.

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 along the way – 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, higher-end hotels in Australia and New Zealand tend to come with a reasonable price point, fairly strong quality, and generous elite treatment. There are some gems out there, such as the Westin Perth, the W Brisbane, and The Tasman Hobart, and some world-class properties, such as the Park Hyatt Sydney.

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 can go a very long way if you’re planning a trip to this part of the world, but you also might have to rely on last-minute award availability, which can be a bit daunting.

However, it’s well worth the effort, and Oceania as a whole has a lot to offer to many different types of travellers.

Conclusion

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 heading 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 mattress runs were all for.

But don’t forget: 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.