Travel Hacking: How I Unlocked Affordable Adventures Around the World

A Budget Traveler’s Beginning

Travel hacking wasn’t even on my radar when I grew up going on trips with my family. As I got older, I wanted to keep exploring but my budget didn’t always match my travel dreams. For years, I thought points and miles were only for business salesmen with weekly travel and unlimited credit.

Turns out, all I needed was a credit card and a strategy to make travel fit my life – not the other way around.

My First Big Redemption: A Wedding in Italy

In 2019, I was invited to a destination wedding in Tuscany, Italy. My budget was tight, but I was determined to be there. If I was traveling all that way, I wanted to explore more of Italy.

So how did I make it happen?

Step one: The Aviator Red Card

A friend told me about the American Airlines Barclays Aviator Red credit card. At the time, the offer was simple. Make one purchase and earn a 60,000 mile sign up bonus! After purchasing a tank of gas, I had more than enough AAdvantage points to cover my round trip flight to Europe!

The Card That Hooked Me: Chase Sapphire Reserve

Soon after, I opened the Chase Sapphire Reserve. This is the card that truly got me into travel hacking.

Sign up bonus: 50,000 points after spending $4,000 in three months.
My first redemption: A rental car in Italy.

Driving solo in another country is nerve wracking enough, but I also made a rookie mistake. I paid with my credit card and used the Chase “Pay Yourself Back” feature to erase the charge with points… not the best value, but I didn’t know better at the time.

What made me keep it for a year?

Priority pass lounge access
Global entry
$300 annual travel credit

Even with those perks, the $550 annual fee was still a stretch for me. Since I wasn’t traveling enough to maximize all the perks, I downgraded after a year to the Chase Freedom Unlimited, with no annual fee.

Lessons Learned Along the Way

What I didn’t realize at the time was that there were far more valuable ways to redeem points. Over time, travel hacking became less about chasing points and more about designing trips that felt possible on any budget.

I’ve learned the ends and outs of transfer partners. Over the past few years, I’ve branched out:

American Express Membership Rewards Points
Capital One Miles
Chase Ultimate Rewards

My favorite? Transferring Chase points to Hyatt. In the past year alone, I’ve booked multiple hotels both in the U.S. and abroad with nothing out of pocket.

What I’d Do Differently If I Started Today

Track points from day one.
Use a simple spreadsheet or an app like Travel Freely to make it much easier and faster to get free travel.

Learn transfer partners before redeeming.
For example: if flying from the east coast, Capital One Miles → Air Canada Aeroplan can stretch your value more than the standard 1 cent per mile.

Pace yourself with new cards.
No more than one every 90 days and only if you can pay it in full.
Don’t ignore flexible points.
Programs like Amex Membership Rewards or Chase Ultimate Rewards paired with transfer partners will save you thousands of points over time.

The Golden Rule of Travel Hacking

The golden rule of travel hacking? Never carry a balance. I’ve never paid interest on a credit card.

Interest wipes out any rewards. I’ve always set autopay for the full statement balance. Today I have 10+ credit cards and my credit score is still over 800!

What’s Next

This is just the beginning of my travel hacking journey. In my next article, Travel Hacking 101, I’ll share:

How to actually book flights with points
The best hotel travel partners
My go-to strategy for getting started with points and miles

Let’s Talk

Have you ever booked a trip with points, or is this your first time hearing about it? Drop a comment below. I’d love to hear your story or the mistakes you’ve learned from.

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