How a Tank of Gas Got Me to Italy (And Why I’ve Never Paid for a Hotel Since)

It started With a Wedding Invitation

Travel hacking wasn’t even on my radar when I growing up. As I got older and wanted to keep exploring, my budget didn’t always cooperate. For years, I assumed points and miles were for business travelers with corporate cards and expense accounts. I had neither.

What I did have was a credit card, a wedding invitation to Tuscany, and a budget that definitely didn’t cover a transatlantic flight.

This trip changed how I travel. Not because it was perfect, but because it showed me that getting there was more possible than I thought.

The First Redemption: Italy on a Tank of Gas

A friend told me about the American Airlines Barclays Aviator Red credit card. The offer at the time: make one purchase and earn 60,000 AAdvantage miles.

I bought a tank of gas. I had more than enough AAdvantage points for a round trip flight to Europe.

That’s not a trick. That’s just how sign-up bonuses work when you’re intentional about it.

The Card That Actually Taught Me to Play

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

1. 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.

2. 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.

3. Pace yourself with new cards.
   No more than one every 90 days and only if you can pay it in full.
   
4. 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!

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.

📌 Save this post for later on Pinterest!

Save to Pinterest