The Hardest Destinations for Travelling on Points

As opposed 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.

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 Eastern Canada).

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 54,000 – 66,000 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…