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 on my radar 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 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

Shortly after, I opened the Chase Sapphire Reserve. This is the card that changed how I thought about points. 

• Sign up bonus: 50,000 points after spending $4,000 in three months.
• My first redemption: A rental car in Italy using the Chase :Pay Yourself Back” feature.

The honest part: that was a bad redemption. Pay Yourself Back gives you roughly 1.5 cents per point. Transferring to a hotel or airline partner can get you two to four times that value. I left a lot on the table, but I didn’t know better at the time.

What kept me using it for a year?

• Priority pass lounge access
• Global entry credit
• $300 annual travel credit

Even with those perks, at $550 per year, I wasn’t traveling enough to justify it. After a year, I downgraded to the Chase Freedom Unlimited, with no annual fee and still earns Ultimate Rewards points. 

What I’d Do Differently Starting Today

1. Track your points from day one. 
   A simple spreadsheet or an app like Travel Freely saves you from the mental math later.

2. Learn transfer partners before you redeem.
   The difference between redeeming at face value and transferring to a partner can be worth hundreds of dollars per trip. For example: Capital One Miles transferred to Air Canada Aeroplan often stretches your value more than the standard 1 cent per mile.

3. Don’t rush new cards.
   One every 90 days max, and only if you can pay the balance in full every month.

4. Prioritize flexible points currencies.
   Chase Ultimate Rewards and Amex Membership Rewards give you options. Options are worth more than locked-in airline miles.
   
   My favorite transfer right now: Chase Points to Hyatt. In the past year alone, I’ve booked multiple hotels, in both the US and abroad, with nothing out of pocket.

The Golden Rule of Travel Hacking

Never carry a balance. Not once.

Interest charges erase every reward you’ve earned. I’ve always set autopay for the full statement balance. I currently have 10+ credit cards and a credit above 800. The cards work for me – not the other way around.

What This Blog Is Actually About

Points and miles are a tool. What I care about is where they take you.

For me that’s trails, mountains, places that feel far from everything, and trips that don’t require a week of recovery afterward. I’ll share the full booking breaksdowns: what I redeemed, what it cost in cash, what was worth it, and what the experience was actually like on the ground.

Next up: how I planned a Lake Tahoe hiking trip almost entirely on points and what I’d do differently.

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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