Value vs. Enjoyment: How Do Points Shape the Way You Travel?

In this post, I wanted to think about the question: does Miles & Points change the way you travel, besides getting access to a nicer airplane seat and fancier hotels?

How is the act of travelling, from the inspiration behind the trip to the actual journey itself, shaped and molded by constraints you face as you navigate the Miles & Points landscape, such as redemption sweet spots, limited award space, and varying value propositions?

To what extent does the pursuit of the highest nominal value, in the metric of cents per point (CPP), drive your travels? And does it do so at the expense of how much you would truly enjoy the trip (i.e., your personal, subjective notion of value) in the absence of Miles & Points?

Flexibility Is A Double-Edged Sword

One of the central tenets in Miles & Points is that flexibility is key if you want to maximize the value of your points, and I think this commandment cuts at the heart of the Value vs. Enjoyment debate.

There’s no denying that, for those who primarily redeem points for travel, the choice of destinations isn’t entirely governed by one’s own deepest desires; instead, the realities of mileage balances, well-known reward sweet spots, and award availability often play a much larger role than we think. 

To take an example, the original goal behind my Luxury Hotel World Tour at the turn of the year was to spend another indulgent few weeks in South East Asia, but since I had booked that trip about two months before the date of departure during peak travel season, I had extremely limited award availability to play with. 

In the end, I couldn’t find a reasonable way to fly out all the way to South East Asia directly, so I invoked the principle of flexibility (in more ways than one; you can read about the entire thought process behind booking that trip in this post) and basically decided, “Oh, I guess we’ll have to spend New Year’s Eve somewhere in Europe to break up the journey then. Hmmm, Paris is always a good idea, so let’s do that.”

New Year’s Eve in Paris

New Year’s Eve in Paris

As you look to redeeming your points, you’ll inevitably run into a similar situation where the ideal “10/10” destination in your heart of hearts is difficult to accomplish due to limited award space or a lack of reasonable redemption options, whereas the still-enjoyable-but-less-ideal “8/10” destination has bucketloads of business class award seats available.

In this scenario, do you choose the 8/10 destination to treat yourselves to a good time while redeeming your miles for great value, or do you go ahead and pay cash or redeem miles at a lower value to make your 10/10 dream come true? 

The game of Miles & Points is one that peppers us with endless obstacles and conundrums on our way to winning big, and being flexible is widely touted as the ultimate answer – as if to say, “well, if your desired trip during your desired dates on your desired routing happens to be unattainable, then simply desire other stuff as well.”

But by its very nature, being flexible can also rob you of your dream trip as you choose to settle for another mileage redemption with fewer obstacles in the way. Maybe being in Bali or Langkawi for New Year’s Eve, as we had originally conceived for the trip, would’ve been the most magical occasion and would’ve more than justified having to fly a convoluted five-stop routing on the way to South East Asia – I’ll never know.

The Allure of Maximizing Value

It’s no surprise that Miles & Points tends to attract a certain kind of crowd: those who are obsessed with the idea maximizing stuff across all aspects of their lives. I’d firmly place myself in this camp, and I’m sure many of you might identify this way as well. And even if you don’t, I’d venture to say that earning and redeeming points at least puts you in the mindset of thinking about getting the maximum gain with the minimum output. 

This desire to maximize your gains shows up on both sides of the Value vs. Enjoyment debate, because what maximizes value on paper isn’t always the same as what maximizes enjoyment, and indeed, the two can be diametrically opposed just as often as they happen to overlap.

I can’t deny that the desire to maximize on-paper value is a huge motivation behind many of the trips I take. For example, the original idea behind my Middle East trip this summer was to simply spend a few weeks in Turkey, Jordan, Oman, and the United Arab Emirates.

But then the Marriott Bonvoy sweet spot of redeeming 60,000 points for top-tier luxury hotels happened, and so I thought “there’s no way I’m not stopping by Mystique and Al Maha for a few nights each during this trip”, and proceeded to plan a few weeks of the trip around those sweet spots instead.

Don’t get me wrong, Mystique’s incredible vistas treated me to an unforgettable occasion, but at the same time, I probably wouldn’t have visited Santorini on this trip otherwise, and as a result I had to cut short my time in Jordan and Oman (and our time in those countries felt more rushed than they otherwise would’ve been). I also gave up a side-trip to Abu Dhabi in exchange for staying at Al Maha for three nights. 

Thankfully, looking back on my Middle East trip, I’m happy to say that the decision to pursue greater value in picking those luxury hotels delivered enough enjoyment to offset the loss of some meaningful travel time in the Middle East…

…but that’s not always necessarily the case. For example, for an upcoming New Year’s Eve trip in December, I had speculatively booked a few nights at the Gritti Palace in Venice and the W Verbier in Switzerland back when the Bonvoy deal of 60,000 points per night was still on. 

There’s no question that the Gritti Palace is a supreme value maximizer, since a room on the banks of Venice’s Grand Canal retails for over $1,000 per night over New Year’s Eve.

The Gritti Palace, a Luxury Collection Hotel, Venice

The Gritti Palace, a Luxury Collection Hotel, Venice

However, having been to Venice twice already, neither Jessy nor I felt particularly enthusiastic to return this time around, so after initially getting Marriott to honour the reservation at the old points rate, I eventually changed my mind and cancelled the reservation, and we’re going to spend New Year’s in London instead before heading to Verbier for a few days on the slopes. 

This was a decision where I went with what would maximize my enjoyment rather than delivering value on my points – after all, I could always save those points for the next trip when I’d hope to maximize their value as well.

I’m sure many of you have gone through similar thought processes as you plan your trips, as the allure of maximizing value is undeniably strong. But it’s definitely worth thinking about how many of your decisions are driven by your genuine endogenous travel goals, and how many are driven by extraneous motivations like maximizing the value of your points.

Dom Perignon Rosé 2006 on Emirates First Class

Dom Perignon Rosé 2006 on Emirates First Class

Indeed, potentially the most insidious manifestation of the pursuit of value is when a certain award chart sweet spot is about to go away. For example, about half of the Points Consulting requests that I had received over the week of August 31, 2019 came from people who basically said “I don’t really care where I go, I just want to fly a three-stop Aeroplan Mini-RTW in business class before it goes away, help me make it happen.” 

(And let’s be clear: I’ve very much been guilty of this FOMO-driven type of travel, too, so I’m not claiming any sort of high ground here – I just think it’s worth recognizing.) 

At a more micro level, the desire to maximize value every step of the way can also be witnessed in our choice of business class carriers (does a lie-flat all-aisle reverse herringbone seat warrant taking a more convoluted routing than an angled-flat 2-2-2 configuration?)

It affects how we choose to spend time at the destination (do we indulge in the complimentary elite Happy Hour at the hotel bar, or head out to the local pubs and brews?)

Breakfast at the  St. Regis Bali

Breakfast at the St. Regis Bali

And yes, it even plays out in our choice of diet when travelling (should we guzzle down every morsel of food presented to us onboard First Class, in the à la carte dining room of the First Class Lounge, or even at the St. Regis Bali’s gargantuan breakfast… or you know, should we eat reasonable portions like reasonable people?) 

When you boil it down, the game essentially consists of a never-ending series of little trade-offs between these two often divergent ends of Value vs. Enjoyment.

The Journey vs. The Destination

Ultimately, the search for answers to this question is governed by our own travel preferences. Do you care more about the journey or the destination, or do you take equal enjoyment in both?

If it’s the former, do you really care about travel at all, or are you more interested in sampling the elusive experiences of luxury travel?

And if it’s the latter, are you more focused on specific types of trips to specific destinations (i.e., outdoor adventures, city breaks, exotic cultures, etc.) or are you more like me, with incurable wanderlust and an ability to derive satisfaction from visiting any spot on Earth as long as it’s new and exciting? 

Alas, the beauty of Miles & Points lies in the fact that it can be adapted to fulfill your needs no matter how you’re answered those questions.

Emirates 777 New First Class

Emirates 777 New First Class

If you’re all about the business class and First Class flights and the pursuit of a luxurious lifestyle, well, using rewards points is by far the best way to make it happen, and you’ll be unlocking spectacular value for your points in doing so. In fact, the ideas of value and enjoyment pretty much overlap, so you don’t have much to think about – simply book the next premium travel experience that tickles your fancy, and off you pop.

On the other hand, if you primarily care about visiting a few select destinations, Miles & Points can easily make the fulfillment of your hobby much more affordable and enjoyable, but as we touched upon earlier, though, you’ll need to put some thought into how much enjoyment you’d be willing to sacrifice in the name of value.

And if you’re anything like me, with an appreciation for the journey and the sense of constantly being on the move that’s matched only by an enthusiasm for all that the world has to offer, then Miles & Points is pretty much a custom-built solution for your life. 

You can’t really go wrong either way when faced with the choice, because whether you favour value over enjoyment or vice versa on this one particular trip, you’ll still have a great time from the mere act of travelling, and you’ll always be able to swing in the other direction on the next trip. 

I can only speak from my own perspective, but as someone in this position, I do feel truly fortunate to have discovered Miles & Points and to have allowed it to mould my travel style in the way it has.

Sometimes, as in my recent Middle East trip, I’ll go out of my way to experience a high-value redemption that maximizes my CPP. Meanwhile, on other occasions, like my South America trip last year or my choice of London over Venice for the upcoming New Year’s Eve, I’m sacrificing a bit of nominal value in favour of listening more to my adventurous spirit. 

And those rare occasions when the two objectives can be fulfilled at once, as in my audacious Mini-RTW to Ghana, Australia, and Micronesia, tend to make for some of the most memorable trips I’ve ever taken.


A key doctrine in Miles & Points is the idea of maximizing value, but alas, the highest value on paper doesn’t always match what would give you, as the traveller, the greatest enjoyment.

While it can be thrilling to maximize your CPP and book a spectacular trip that had a market value in the mid-five-figures, it shouldn’t necessarily be the ultimate guiding force behind how your redeem your points. True maximization is subjective to each and every one of us, and it’s up to you to decide how to make the most of what Miles & Points gives you: unparalleled access to experiences that most of the world will never get to enjoy.

I’d love to hear your thoughts in this discussion as well, so let me know in the comments where you find yourself on the Value vs. Enjoyment spectrum.