How I Booked My First Points Trip

You know origin stories — like how the superhero became super? 🦸‍♂️

Think Marvel blockbusters like Iron Man, Captain America: The First Avenger, Spider-Man (pick your fave Spidey), or DC’s many Batman iterations.

Love ‘em or hate ‘em, they’re helpful for understanding the character and how they got their special powers.

So pull up a chair for my points-and-miles origin story — except instead of saving the world via radioactive spider-bite-induced powers or flying, I’m saving $$$ by booking with points. 💁‍♀️

How It All Started

Like Batman’s Bruce Wayne, this story begins when I was just a little kid.

In this case, a little kid squished into the backseat for many, maaany road trips. 🚗

Now don’t feel bad for me, because some of those road trips did end up at a Disney theme park. I also got to take some cool Caribbean cruises. All in all, I had it pretty good.

But I desperately wanted to see the world, y’all.

Blame it on my Disney movie childhood — I felt like there was so much to see out there that I was missing out on, and I just needed to figure out how to make it happen.

School, work responsibilities, finances, being scared to travel alone, a global pandemic… the excuses always seemed to pile up.

So in 2022, I put my foot down and decided I was finally going to make my dream trip happen: I was going to Italy.

I just had to figure out how to pay for it first. 🤔

Earning the points (accidentally??)

Now this origin story, I guess, belongs in part to my husband too, though I’m not sure he’d enjoy being labeled my trusty sidekick. 😬

You see, my ✨ very wise ✨ husband had opened a Chase Sapphire Preferred® Carda few years back because he’d read somewhere (? 🤷 ?) that it was a great card for travel. So we’d been using it for everyday purchases and paying it off each month, much like a debit card, for years.

We had also recently remodeled part of our house, and instead of paying for it with cash or taking out a loan, we’d opened a Chase Freedom Unlimited® — a $0 annual fee card that offers 0% interest for 15 months. Using that, we paid for the remodel upfront and diligently paid it off over the next 15 months, before the interest rate kicked in.

Without even realizing it, we had accidentally accumulated a sweet little stash of Chase Ultimate Rewards points. 💰️

We now had some of the most desirable points in the travel world — we just didn’t know it yet (nor did we know how to use them).

The Art of Redemptions

I wish I’d been subscribed to the Daily Drop newsletter back then. It would’ve saved me sooo much time. 😓

After a deep research dive into all the award travel info I could find on the internet, I learned I basically had two options:

1. Redeem them in the Chase Travel portal.

2. Transfer them to a travel partner.

3. There’s technically also an option to redeem them for cash back — but that’s not the story here (also, spoiler alert: it’s not a great option).

Now which to choose??

Neither option is bad, per se, but there does tend to be a better option — transferring points to partners typically gets you more value per point.

Somehow, I made the wise choice to transfer points to one of Chase’s travel partners.

The Deal is in the Details

I found flights on United Airlines from Houston to Rome and saw that I could either pay cash or ~30,000 points one-way* per person in economy.

I then confirmed that United Airlines was a Chase transfer partner… and yep, they were! ✅

So, I had more than enough points to book that flight!!

Buzzing with excitement that this trip might just be possible, I searched for a return flight that fit my dates and fell in my points price range.

Sure enough, I found return flights from Venice for about the same redemption value.

Jackpot!

So I hustled back to my Chase app, found my little points stash, clicked Redeem Rewards, and figured out how to quickly transfer them to United.

In mere moments, my points appeared as United MileagePlus Miles! ✈️

I went back, added the flights I’d found earlier to my cart, and checked out, paying with my freshly transferred miles and cash for the fees.

In total, I booked round-trip tickets to Europe for my husband and me for 126,000 miles and ~$340.

I really was going to Italy. 🤯 

Looking back, the giddy adrenaline rush of figuring this out and successfully booking it did kinda feel like I’d just discovered a superpower.

The Mistake that Haunts Me

Flights secured, I set about booking our accommodations for our two-week trip.

Slow Travel Success

Our trip started with a week-long tour of Tuscany, booked with a local slow-travel company that arranged everything during our stay.

Slow travel is just what it sounds like: a slower, more mindful way of seeing a small region with a focus on immersing in the local culture and community.

We were hosted for the week in a wonderful agriturismo, a working farm that hosts guests much like a bed-and-breakfast. In this case, we stayed at a centuries-old farmhouse on a property that produces its own olive oil.

We spent the next seven days being ferried in an awesome retro van to dreamy Tuscan villages, a pasta-making class with a private opera singer, family-owned wineries with wine tastings, and fresh farm-to-table meals that taught me what good tomatoes should taste like. 😋 

Riding with the windows open, wind in my hair, listening to Italian classics as we wound through the hills of Tuscany at sunset will live rent-free in my mind for eternity. 😍 

We even attended a local community pizza-and-wine pairing event held at a vineyard.

Tuscany had it all, y’all.

Deliciously simple food teeming with flavor. Beautifully preserved villages brimming with history. Gorgeous sunsets over rolling vineyard-covered hills dotted with towering cypress trees.

It was a week spent with locals who became friends that I was inexplicably sad to leave.

Points Make Cash Opportunities Possible

While admittedly a little pricey, I consider the tour 1000% worth it and still one of my favorite weeks ever.

And if I’m honest, I felt a little better about spending a bigger chunk of cash on such a unique experience because I knew I had saved money on our flights.

So, yes, sometimes points aren’t the answer, but they can certainly help make more expensive tours like this possible.

Where I Dropped the Ball

For the second week of our trip, however, I had pieced together an itinerary of hotels that I found online and either booked directly or through a third-party booking website.

And while they were all decent picks, I left sooooo many points on the table, y’all. 😭 

I don’t even remember if I tried to book hotels with points or knew that was possible.

But even if I was going to pay cash anyway, I could’ve booked through the Chase Travel portal and earned 5x points on every dollar we spent on hotels.

Which, for Europe in June… would’ve been a fair amount of points.

And a quick search shows that the actual hotels we stayed at are, in fact, available to book in the travel portal.

Not to mention, the Sapphire Preferred comes with a $50 credit that can be used when booking hotels in the Chase travel portal. 🤦‍♀️ 

In short, I could’ve saved 50 bucks and earned thousands of points.

Big missed opportunity, y’all, and I’m still a little sad about it. 😞 

What I’d Do Differently Today

Now, to be clear, I still LOVED my trip.

It was everything I wanted it to be and more. Minimal regrets — except maybe I would’ve worn better shoes to walk miles around the cobblestone streets of Rome. 🫠 

But after years of repeating this method, learning more, and improving my process, I now know I could’ve done things even better.

For instance, I could have:

• Booked my flights with another program like Virgin Atlantic, Aeroplan, or Flying Blue and probably found a much better redemption price for economy tickets.

• Redeemed about the same number of points for two one-way business class seats through a program like Aeroplan.

• Re-positioned to another domestic airport to take advantage of a business class deal if there weren’t any from my home airport.

• Redeemed some of my UR points to save big time on hotel stays (looking at you, Hyatt 👀 ).

• Booked hotels through the Chase travel portal to earn 5x points back on hotels.

• Used a shopping portal like Rakuten to earn points on some of the tours we booked (the number of points I missed out on for Viator and GetYourGuide bookings over the years before I learned this trick makes me cringe).

• Opened a different card, like the Capital One Venture X Rewards Credit Card, to get lounge access for the 5-hour layover we had in LHR and redeem the $300 travel credit it comes with for one of our hotel stays.

There are so many different ways to book or maximize an award trip, and the more I learn about points and miles, the more value I want to try and squeeze out of the cash I spend and the points I redeem.

But at the end of the day, as long as you are happy with your redemption, it’s a win. 🎉 

Taking Up the Mantle

So, if you’ve been looking for a way to start your own points and miles saga (or just plan that dream trip), here are a few actionable steps I’d pass on to any aspiring points travelers:

1. Open a beginner travel card.

2. Put your everyday purchases on it and pay it off each month, being sure to hit the minimum requirement of the welcome offer for your card.

3. Familiarize yourself with your card’s transfer partners.

4. Find available award flights with one of those partners.

5. Transfer your points to book your award!

And if you get stuck or struggle to find an award flight, there’s always Daily Drop Pro, the best award travel sidekick.

Cause let’s be real, some of the biggest superheroes used all the cool gadgets and digital assistance. Looking at you, Iron Man and Batman. 👀 

If it feels daunting, have no fear. It really can be as simple as I described, and like everything, it gets easier the more you do it.

So whether it’s a superpower or more of a muscle you build with practice, saving money on dream trips by booking with points is a flex all the same. 💪