100 Days Travel Hacking Asia as a Couple: Lessons, Mistakes & What We’d Do Differently

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One hundred days. Eight countries. Over $20,000 CAD saved in hotels and flights through points, certificates, and elite status benefits. Dozens of free nights at properties ranging from a boutique Chiang Mai guesthouse during the Lantern Festival to the St. Regis Beijing to the InterContinental Da Nang Sun Peninsula Resort.

We’re home now. The bags are unpacked. The jet lag has dissolved. And from the slightly surreal vantage point of being back in our regular lives after three and a half months of constant movement, we’ve been doing a lot of reflecting.

Not just on the trip — on what the trip taught us. About points and strategy and the mechanics of travel hacking done well. And about something more fundamental that travel guides don’t usually cover: what happens when two people with different instincts and different styles attempt to execute a complex, multi-program points strategy together across 100 days in Asia.

This is what we learned.

The Travel Hacking Lessons

1. Both People Need to Accumulate — This Cannot Be Overstated

The single most impactful structural decision we made was treating points accumulation as a shared responsibility rather than one person’s project. Both of us held cards, earned points, and accumulated balances across multiple programs simultaneously.

The practical impact of this is enormous. When two people are accumulating instead of one, you build the points war chest roughly twice as fast. More importantly, you build it across more programs — because each person can hold cards and earn in programs the other isn’t covering, which means between you, you have coverage across Marriott, Hilton, IHG, Aeroplan, Avios, Hyatt, and Cathay simultaneously without either person being overextended in annual fees.

On a 100-day trip for two people, the points requirement is inherently doubled. Two free night certificates covers two nights for two people. One free night certificate covers one night for two people. Having both partners accumulating is not a nice-to-have — it’s the foundation the entire strategy rests on.

If you’re planning a big trip as a couple and only one of you is currently points-active, start the other person accumulating now. Give it two to three years and the difference in what you can access will be transformative.

2. Different Currencies for Different Places

One of the most important evolutions in our thinking across the trip was moving away from the idea of a single dominant points program toward a genuine multi-currency approach — where different programs are used strategically for different contexts.

Marriott Bonvoy certificates for premium hotel nights in Vietnam and China. Hilton Honors points for longer stays where the fifth night free benefit multiplies value. IHG points for aspirational properties like the InterContinental Da Nang. British Airways Avios for Accor hotels in Vietnam. Aeroplan for Star Alliance flights across Asia. Cathay Asia Miles for Hong Kong routings. World of Hyatt certificates for peak-demand nights in Hong Kong.

Each program has a context where it outperforms the others. Using the right currency in the right situation — rather than defaulting to one program for everything — is what transformed our points from a modest travel subsidy into a $20,000+ savings engine.

The discipline this requires is knowing your programs well enough to recognise which one delivers best value for each specific redemption. That knowledge takes time to build. Start learning your programs before you need to use them.

3. Start Accumulating Years Before Your Trip — Not Months

We cannot emphasise this enough. The points that funded our 100-day trip were accumulated over two to three years of deliberate everyday spending before we booked a single flight.

Points accumulation is not a sprint. It is a slow, patient process of converting your normal spending into travel currency, gradually, over time. The travellers who execute truly transformative travel hacking redemptions — free nights at the St. Regis, business class flights on Cathay Pacific, a week at the InterContinental on IHG points — are almost always people who started years before the trip, not people who rushed to accumulate in the six months beforehand.

If you’re reading this and thinking about a big Asia trip in the future, the best time to start building your points is now. Not when you’ve decided on your destination. Not when you’ve booked your flights. Now. Every month of accumulation before your trip represents real, deployable value when you finally need it.

4. Don’t Put All Your Points in One Program

Related to the multi-currency lesson: concentration risk in a single loyalty program is a genuine strategic vulnerability that most beginner travel hackers underestimate.

Programs change their redemption rates. Properties leave networks. Award space disappears. A program that delivers extraordinary value for a specific redemption today may restructure its pricing before you get to use your balance. We’ve seen it happen to programs we use and rely on.

Spreading your accumulation across multiple programs means that no single program change devastates your strategy. If one program devalues its awards, your other balances are unaffected. If a specific property leaves one network, you may be able to reach it through another. Diversification in points is as sensible as diversification in any other asset class.

5. Always Book Refundable Rates — Then Monitor for Price Drops

This is one of the most actionable and underutilised strategies in travel hacking, and one we refined across the 100 days.

Whenever possible, book refundable points rates rather than non-refundable ones. Then set a reminder to check the same booking periodically in the weeks before your stay. If the points price drops — and on dynamic pricing programs like Marriott Bonvoy it frequently does — cancel and rebook at the lower rate within your cancellation window. The difference in points is refunded to your account.

Over a 100-day trip with dozens of hotel bookings, this habit returned a meaningful number of points to our balances that we were then able to redeploy elsewhere. It takes five minutes of attention per booking. The return on that time is consistently positive.

6. Flexibility Is More Valuable Than a Rigid Itinerary

The trips where travel hacking delivers maximum value are trips with genuine flexibility. Award space, point redemptions, and free night certificate availability are all subject to constraints that a rigid, fully pre-committed itinerary cannot always accommodate.

Going into our 100-day trip with a framework rather than a fixed schedule — knowing the countries and approximate durations but leaving specific dates and properties somewhat fluid — allowed us to make redemption decisions that a locked itinerary would have foreclosed. When a better redemption became available, we could take it. When a property had no award availability on our planned dates, we could shift a few days in either direction to find a window.

This doesn’t mean planning nothing. It means building enough slack into your plans that the travel hacking strategy can breathe. Over-planning and travel hacking are in tension with each other. Give the strategy room to work.

7. Always Have a Backup Plan

Points don’t always work the way you expect them to. Award space disappears. Programs have technical issues. Certificates have eligibility quirks that only reveal themselves at the moment you try to apply them.

On a 100-day trip, we encountered every one of these situations at least once. What made them manageable rather than catastrophic was always having a contingency — a cash rate monitored on Agoda, an alternative property in the same area, a different program that could cover the same night.

Never be in a position where a single points failure leaves you scrambling for accommodation in an unfamiliar city. Keep the safety nets in place throughout the trip.

What Travelling 100 Days as a Couple Actually Taught Us

The travel hacking lessons are important. But honestly, the deeper lessons from 100 days on the road together were about something else entirely.

One of Us Plans, One of Us Lives in the Moment

Within the first two weeks of the trip it became undeniably clear: Ange plans, Zee lives in the moment.

This is not a new dynamic — we knew it existed before we left. What 100 days of travel did was make it impossible to ignore, forcing us to actually negotiate it in real time rather than letting it exist as a vague background tension.

The planner wants the points researched, the bookings confirmed, the next city’s itinerary roughed out. The spontaneous traveller wants to see what the day brings, to follow an interesting street, to say yes to things that weren’t in the plan. Left unmanaged, these instincts pull in opposite directions and generate friction.

What we learned — slowly, through genuine trial and error — was that both instincts are necessary. The planning created the financial structure that made the trip possible. The spontaneity created the moments that made the trip meaningful. The egg coffee class in Saigon. The hotpot on opening day at Landmark 81. The 20 Hong Kong dollars won at Sha Tin racecourse. None of those were in the plan. All of them were highlights.

The couple that travels well together isn’t the couple where both people have the same instincts. It’s the couple that has learned to value what the other one brings.

Long Trips Reveal Things About Your Partner You Didn’t Know

Three and a half months of constant proximity, in unfamiliar environments, with frequent logistical challenges and occasional genuine stress, reveals things about the person you’re travelling with that regular life keeps hidden.

How they handle being lost. What they’re like when they’re exhausted and hungry and the restaurant they walked twenty minutes to find is closed. Whether they recover quickly from small disappointments or carry them through the afternoon. How they treat service staff in countries where the power dynamic is obviously unequal. What they find funny at 6am in an airport.

We learned things about each other on this trip that years of shared regular life hadn’t surfaced. Some of it was reassuring. Some of it was challenging. All of it was real — and real, in a relationship, is always more valuable than comfortable.

Long Trips Test Your Patience With Each Other

We’re going to be honest about this because every couple travel blog that only shows the beautiful photos is lying to you by omission: 100 days of uninterrupted time together is a lot.

There were days when we needed space from each other and had none. Days when a decision about where to eat became a proxy for something else entirely. Days when the accumulated tiredness of months of travel condensed into a specific irritability that had nothing to do with the person next to you and everything to do with them at the same time.

This is normal. This is what long-term travel together actually looks like. The Instagram version of a couple travel blog shows the sunset views and the matching outfits at famous landmarks. The honest version includes the afternoon where nobody wanted to talk and both people pretended to be very interested in their phones.

What matters isn’t whether these moments happen — they will, they always do — but what you do with them. We learned to give each other space when it was needed, to address things directly when they needed addressing, and to not mistake travel tiredness for relationship problems.

By Seoul, at the end of 100 days, we were a genuinely better team than we were when we left. That’s the honest bottom line.

We Learned Each Other’s Travel Styles at the Deepest Level

There is a version of knowing someone’s travel style that comes from a two-week holiday. And then there is the version that comes from 100 days across eight countries — a knowledge so specific and so tested that it becomes almost intuitive.

By the end of the trip we knew each other’s rhythms completely. How much walking was too much before a break was needed. Which kind of restaurant decision could be made unilaterally and which ones required a proper conversation. When to suggest the museum and when to suggest the café. How to read the other person’s energy at breakfast well enough to know what kind of day was coming.

This kind of knowledge is one of the most valuable things a long trip gives a couple. It outlasts the trip itself — it changes how you navigate everything afterward.

What We’d Do Differently Next Time

We’d Travel Slower

This is the clearest lesson of the entire 100 days: we covered a lot of ground, and there were moments — particularly toward the end — where we felt the cost of that pace.

The destinations we loved most were the ones where we stayed longest. Five nights in Taichung. Five nights in Wangfujing. Five nights in Seoul. The cities and places we passed through in two or three nights left us wanting more. Depth is better than breadth. Staying longer in fewer places consistently produced richer experiences than moving quickly through more of them.

Next time — and there will be a next time — we’d build the itinerary around longer stays with fewer transitions. More weeks, fewer places. More evenings in the same neighbourhood restaurant. More of the specific kind of familiarity that only comes from being somewhere long enough that it starts to feel temporarily like home.

We’d Visit Fewer Countries More Deeply

Related to the above — eight countries in 100 days meant that some destinations never had the time to properly open up. China in particular deserved more. Shanghai, Chengdu, Guilin — cities and regions we talked about the whole trip and never reached.

A future version of this trip might be five countries in 100 days rather than eight. The logistics of travel — flights, new SIM cards, currency exchanges, learning a new city’s transport system — take time and energy that a slower itinerary recaptures and returns to the experience itself.

We’d Do a 100-Day Trip Again

Without hesitation.

The scale of the experience — the breadth of what we saw, the depth of what we felt, the transformation that happens to you and between you over that much time on the road — cannot be replicated in shorter trips. Two weeks gives you a holiday. A hundred days gives you something that changes how you see the world and yourselves in it.

We’d do it again with the lessons learned. Slower pace. Fewer countries. More depth. Both of us accumulating even harder for the years between now and then.

The points are already building.

Our Final Advice for Couples Considering a Big Points Trip

Start accumulating together, now. The earlier both of you start, the more you’ll have when you need it. Treat it as a shared financial goal with a shared reward.

Diversify across programs. Marriott, Hilton, IHG, Hyatt, Aeroplan, Avios — each has a context where it shines. Learn them all and use each where it performs best.

Build flexibility into your itinerary. Points strategy needs room to breathe. Over-planning closes doors that flexibility keeps open.

Have honest conversations about travel styles before you go. Planner and spontaneous can coexist beautifully — but only if both people understand the dynamic and have agreed how to navigate it. Have that conversation at home, not at the check-in counter of a hotel where the points booking didn’t work.

Slow down. The best moments of our trip were almost all in the slower chapters. Let destinations breathe. Let yourselves breathe. The points will get you there — the pace is what determines what you find when you arrive.

And go. Whatever version of this trip you can manage — 30 days, 60 days, 100 days — go. The world is extraordinary and your points are sitting there waiting to take you to it.

For everything that went into funding this trip, read our how we saved $20,000 on our 100-day Asia trip guide. For the full journey from start to finish, our 100-day Asia trip overview is where to begin.

Follow along for the next one: Instagram @angeandzee | TikTok @angeandzee