How I've Been Funding My Travels With Credit Card Points
A beginner's honest account of what worked, what didn't, and where to start.
If you'd told me a few years ago that I'd be booking cruises and hotel stays for (almost) free, I probably wouldn't have believed you. But that's exactly what's happened — and the secret isn't a windfall or a side hustle. It's credit card points, and honestly, it's changed the way I think about travel. Here's a look at the cards I've tried, what worked, what didn't, and what I'd recommend if you're curious about getting started.
Card 1 · The Beginning
Where It Started: The Hilton Amex Card
American Express
Hilton Honors Card
Welcome Bonus
75,000 pts
Spend Requirement
$2,000 in 6 months
Annual Fee
Free yr 1 · $95/yr after
Best For
Hilton hotel stays
My first travel card was the Hilton Honors card through American Express. The sign-up offer was 75,000 points after spending $2,000 in the first six months — which felt very doable for everyday purchases. The card was free for the first year, so the barrier to entry was low, and I was able to use those points to book several Hilton Hotels. For a first foray into the points world, it was a win.
After the first year, the annual fee kicked in at $95. I kept it for two years, but eventually downgraded to the free version because redemption was getting trickier — hard to accumulate points fast enough to cover hotel stays in a meaningful way. Still, while it lasted, we stayed in some genuinely great hotels. No regrets on the experiment.
Takeaway
Great starter card. The welcome bonus alone makes it worth trying — just know the long-term redemption rates aren't the strongest.
Card 2 · The Free One
A Surprise Win: Capital One Venture One
Capital One
Venture One Card
Annual Fee
Free
Recent Portal Bonus
+15,000 pts
Best Feature
Capital One Travel Portal
The Capital One Venture One is completely free — no annual fee — and came with a solid welcome bonus. It's been a low-maintenance card to keep around.
The biggest win came recently when I booked a rental car through the Capital One Travel Portal. Not only was it the best deal I found, but I stumbled onto a promotion I didn't even know was running and earned 15,000 bonus points just for booking through the portal. Sometimes the points gods just smile on you.
Takeaway
Zero annual fee and a solid travel portal. Even if you're not actively chasing points with this one, it rewards you when you least expect it.
Card 3 · The Game-Changer
The Real Discovery: World of Hyatt (Chase)
Chase
World of Hyatt Card
Welcome Bonus
40,000 pts
Spend Requirement
$2,000 in 6 months
Annual Free Night
1 free night / yr
Estimated Savings
$2,000+ in hotels
After a while with the Hilton card, I did some research and landed on what a lot of points enthusiasts already know: Hyatt has one of the best redemption rates per point in the hotel world.
Forty thousand points sounds modest compared to flashier bonuses — but some Hyatt properties cost as little as 8,000 points per night. I booked 7 nights for an upcoming East Coast trip with just 44,000 points total (one of those nights using a free night certificate, which you get once a year just for holding the card). My rough estimate is that we saved over $2,000 in hotel costs on that single trip. That annual free night certificate alone is worth more than the annual fee every year.
Takeaway
Don't let a smaller welcome bonus fool you. Hyatt's per-point value is exceptional, and the annual free night certificate is a deal-sealer.
Card 4 · My Favorite
The Best Yet: Chase Sapphire Preferred
Chase
Sapphire Preferred Visa
Welcome Bonus
100,000 pts
Spend Requirement
$5,000 in 3 months
Annual Fee
$95/yr
Cruise Savings
~$1,000 off
Not long after getting the Hyatt card, I applied for the Chase Sapphire Preferred Visa — and it's become my favorite travel card, full stop.
The welcome offer was 100,000 points after spending $5,000 in the first three months. We used some points on a hotel and put the rest toward a cruise. The points didn't cover the entire cruise, but they knocked off close to $1,000 — and booking through the Chase Travel Portal came with an additional $300 in onboard credit. That's a remarkable chunk of a vacation covered by a card we were already using for everyday spending.
The $95 annual fee is easy to justify with the perks: a $100 hotel credit per year, TSA PreCheck reimbursement, a free year of Apple TV+, and various rotating offers. But the feature I love most is the ability to transfer points to partners — including Hyatt. Most travel cards have transfer partners, and using them strategically is where points really start to multiply in value.
Takeaway
If you're going to get one travel card, this is the one I'd point to first. The welcome bonus, the perks, and the transfer flexibility are hard to beat.
Stay Informed
The Newsletters That Changed Everything
Part of making this all work is staying on top of new offers and the best redemption strategies. A few newsletters I've found genuinely invaluable:
These don't just show you new sign-up bonuses — they help you understand the strategy behind points: when to transfer, when to redeem direct, and how to squeeze the most value out of what you've already earned. Subscribing to even one will shift how you think about all of this.
The Big Picture
Credit card points aren't a magic trick, and they work best when you're spending on things you'd already be buying. But if you pay off your balance each month and approach it with a little strategy, the savings can be genuinely significant — free hotel nights, huge cruise discounts, and perks that add up fast.
Start with one card, earn that welcome bonus, and see how it feels. The learning curve is shorter than you'd think — and the reward is, literally, going places.
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