The Middle Ground Between Cash Travel and Travel Hacking
For a long time, I thought points and miles travelers either paid for everything with points or they weren’t really doing points and miles at all. At least, that’s what you’d think from watching ten-second social media clips.
The reality has been much different.
Today, I use a combination of points and cash on almost every trip. Sometimes points cover flights. Sometimes they cover hotels. Sometimes they stay untouched because there may be a better use for them later.
But it took me years to arrive at that mindset.
The Trip That Changed Everything
When I first started collecting points, I wasn’t transferring them to airline partners or searching for premium cabin awards. Most of my early redemptions were much simpler: I used points through credit card travel portals to offset costs.
One of my first true redemptions was a summer trip to London. I used points from the welcome bonus on the Chase Sapphire Reserve to offset a round-trip flight and paired them with a welcome bonus from the American Express Marriott Brilliant card to book a week at the Marriott Canary Wharf.
Looking back, I know this wasn’t an optimized redemption. I could probably get much more value from those points today. But that’s also kind of the point: this was the first time points meaningfully changed what I could do with a trip.
In fact, I almost didn’t take it. I changed plans fairly close to departure, and by the time I was ready to book, the flight cost about $200 more than when I’d first started looking. Adding a week-long hotel stay would have pushed the cost even higher.
Using points didn’t make the trip free. It made the trip possible. And that mattered far more than whether I’d squeezed the maximum value out of every point.
It was my first solo international trip, and in many ways it launched the style of travel I still enjoy today. Until then, most of my travel revolved around coordinating with family or friends. London showed me that I could confidently travel on my own, and enjoy it just as much.
I also realized I didn’t need to split a hotel room with someone else to make a trip affordable. The flight had been partially offset with points, and the hotel was covered by a welcome bonus. Suddenly, solo travel felt much more accessible.
That experience made me want to learn more.
I still carry the Marriott Brilliant today, nearly three years after that original welcome bonus was spent. It’s not an everyday spending card for me, but I still pull it out when I’m booking Marriott stays. Between Marriott Platinum status and the annual 85,000-point free night certificate, it’s earned a specific place in my wallet—and become my excuse for one splurge Marriott stay each year.
Only later did I discover transfer partners. One of my favorites eventually became Virgin Atlantic. I’ve regularly found flights from JFK to London for as little as 6,500 points in economy and occasionally under 20,000 points in premium economy. But before you start assuming your next trip to London is practically free, remember to budget for taxes and fees—London award flights can come with some of the highest surcharges.
That’s when I realized there was an entirely different side of points and miles I hadn’t explored yet. My first London redemption may not have been optimized, but it did exactly what I needed points to do: it got me on the trip.
Our family trip to Spain was already starting to reflect the way I travel today: a mix of points and cash. We used points to help cover the flights and paid cash for our hotels, choosing each based on what made the most sense for the trip rather than trying to force points into every booking.
Learning to Earn Is Only Half the Story
As my interest grew, I became the friend who volunteered to put the group dinner on their card and collect Venmo payments afterward. I paid attention to welcome bonuses, category spending, loyalty programs, and ways to earn more points from expenses that were already happening.
One of my biggest early wins came while planning a trip to Malaysia with two friends. They were perfectly happy letting me book the flights, which meant I could put three round-trip tickets on a premium travel card and earn a significant number of points from spending we were going to make anyway.
For a while, earning was the easy part to focus on. Watching points accumulate felt like progress, and I got much better at figuring out which card to use, when a welcome bonus made sense, and how to earn more without spending more just for the sake of points.
But earning points was only half the equation. The other half was learning how and when to use them and when paying cash might actually be the better choice.
And I’ve learned that sometimes saying no to a redemption is just as hard, if not harder, than watching your points balance drop after finally booking one. When you’ve spent months earning points for travel, there’s a temptation to use them simply because you can. But having points available doesn’t automatically make using them the best decision.
Learning when not to redeem them has become just as important to my points strategy as learning how to earn them in the first place.
When My Family Finally Understood
My friends were the first to see the benefits. Many watched me use travel rewards to reduce costs, access airport lounges, and take advantage of perks that made trips easier. Over time, most eventually picked up at least one premium travel card of their own.
My parents were a different story.
For years, all they really saw was me constantly booking trips. They didn’t see the points balances, welcome bonuses, or planning happening behind the scenes; they just noticed that I seemed to travel frequently without spending nearly as much as they expected. For the last few years, my out-of-pocket costs for flights, especially international ones, have often been surprisingly low thanks to points and miles.
As we started taking bigger trips together, though, they began experiencing the benefits firsthand. TSA PreCheck, Global Entry, airport lounges, and other travel perks slowly started making an impression.
The real turning point came during our Egypt and Jordan trip. Points helped us stay at Marriott and Hilton properties that became part of the experience themselves, with resort settings, generous breakfast buffets, lounges, and occasional upgrades. For the first time, my parents weren’t just hearing me talk about points and miles. They were seeing what all that planning could actually add to a trip.
And apparently, it worked a little too well.
Now my dad will ask me what kind of points we’re trying to earn so he knows which card to use. My sister has started volunteering her card at family dinners because she wants the points. Somewhere along the way, I went from being the person everyone wondered about to having competition for who gets to pay the bill.
Both of my parents have since opened travel cards of their own, including the Capital One Venture X and Atmos Infinite card. And their redemptions have reinforced another part of my philosophy: not every use of points needs to be exciting to be valuable.
Atmos points, for example, have allowed them to fly directly from their local airport to Philadelphia for as little as 4,500 points. There’s nothing glamorous about that redemption, but it makes visiting family easier and saves cash for bigger trips later.
Sometimes that’s exactly what I want points to do.
Using points strategically can leave more room in your travel budget for the experiences you actually came for, like guides and a bucket-list sunrise hot air balloon ride over Luxor.
The Middle Ground
Long gone are the days when I thought I had to use points to cover an entire trip to feel like I was winning at the points game.
I’ve stopped measuring a good redemption by whether I got the absolute highest value from every point. Some of my favorite trips certainly wouldn’t win that contest.
London wouldn’t. Egypt wouldn’t. Spain certainly wouldn’t.
What mattered wasn’t maximizing points. It was maximizing travel.
I’ve also come to think about points and miles in seasons. Some trips are redemption trips. Some are earning trips. And some are a combination of both.
Our family travel journey is a good example. It started with paying cash for a trip to the Amalfi Coast, but that spending also helped me earn a welcome bonus and additional points from the bookings themselves. That trip helped earn points I could use to make the next one better.
By Egypt, I was covering hotels with points while paying cash for our long-haul flights. I wrote more about that approach in Using Points for Hotels Instead of Flights: My Egypt and Jordan Strategy. In Spain, miles helped cover our premium economy flights while we paid cash for accommodations and most expenses on the ground.
Those cash expenses aren’t a failure to “win” at points. They’re part of the cycle. Some trips use the points I’ve built up, while others help me earn toward whatever comes next. It’s an idea I explore more in Are You Building, Earning, or Burning Points?
There’s also a practical reality behind my approach: I’m not sitting on a million points. Not even if I added up every points currency I have. Not even close. And I’m not always booking for one person.
A redemption that looks reasonable for a solo traveler becomes a very different calculation when you’re booking three or four seats. My family now has travel cards of their own, but I’m still planning most of our trips and often using my points to fill in the gaps. When you’re traveling as a family, you simply can’t do everything with points the way you sometimes can when traveling solo.
That’s why not every aspirational redemption is worth pursuing. I would have loved to fly business class to Egypt, but even economy awards were pricing around 80,000 points round trip per person. Across several travelers, we’d have consumed most of our available points on one part of the trip.
The goal isn’t to fly business class at all costs. The goal is to take the trip.
Now, as I plan Japan with my parents, I’m looking at a mix of business class and premium economy. Once again, the question isn’t how much of the trip I can cover with points. It’s where will our points make the biggest difference, and where does paying cash make more sense?
For an overnight flight, arriving rested with my parents may be worth a significant number of points. Somewhere else, paying cash may be the smarter choice.
That’s the middle ground I’ve landed on. Points and miles work best when they support the travel I want to take, not when they dictate it.
At the end of the day, I don’t remember the cents-per-point calculation. I remember strolling through Tossa de Mar on the Costa Brava with my family.
Final Thoughts
Most travelers don’t need to choose between paying cash for everything or turning points and miles into a full-time hobby. There’s a lot of room in between.
For me, that means using points where they’ll make the biggest difference and paying cash when that makes more sense. Sometimes that’s an aspirational hotel or a more comfortable overnight flight. Other times, it’s a 4,500-point flight that gets my parents to Philadelphia.
It may not always create the most impressive redemption story, but it has allowed me to travel more often, travel farther, and share those experiences with the people I care about.
And that’s worth far more to me than winning at the points game.
Continue Learning
If you’re interested in how points and miles fit into the way I travel, these articles build on the ideas from this post:
- Are You Building, Earning, or Burning Points? — the framework I use to decide when to earn, save, or spend my points.
- Could the Chase Sapphire Preferred Be the Best Way to Start Earning Travel Points Right Now? — the card that started my own points journey.
- Ready to Level Up? Why the Capital One Venture X Might Be Your Next Travel Card — how I think about adding a second premium travel card once the basics are in place.
Work With Me
You don’t need to figure out your points strategy entirely on your own. If you have a trip in mind but aren’t sure what points to earn, which cards make sense for your upcoming spending, or where points could make the biggest difference, I can help you build a strategy around the travel you’re already planning.