February 2019

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Before you dive into this, please note that my Travel credit cards page offers an exhaustive guide to credit card points. This post is intended to be a fun little anecdote that makes all the points real.

Now to the juicy stuff: how I redeemed my 50,000-point Chase Sapphire Preferred acquisition bonus (after spending $4,000 in three months; easy if you can put rent on your credit card) for an all-inclusive resort valued at approximately $1,100.

First things first

When I got my acquisition bonus, the Chase Ultimate Rewards portal valued it at approximately $683. Not bad, I thought, I’m sure I can get a few nights at a hotel for that much.

But my “points strategy” changed as I began exploring the portal. Rather than using them incrementally over time (5,000 here, 8,000 there) as I spent weekends in various U.S. cities, I started to think about how spending $200 or $300 here and there wasn’t too financially taxing.

In other words, I budget for a few hundred dollars a month in travel expenses, so it doesn’t really bother me.

Spending several (like, MANY) hundreds of dollars in one sitting, though, definitely hurts, and I couldn’t see myself throwing down $500+ for an international-style trip without some serious planning.

So, my strategy was: blow the whole wad in one sitting for a soul-crushingly awesome experience that I would not otherwise pay for. 

Now what?

Being the slave to spreadsheets that I am, I began combing through the Ultimate Rewards portal and keeping track of the frontrunners. I had already decided on Cancun, which, looking back, was solely because of the flight loads that weekend — a factor that was later rendered moot since I purchased the flights anyway.

But Thomas and I had a lot of fun in Cabo last year, so I thought the other side of Mexico may be fun—especially since Mexican tourist destinations offer a LOT of inexpensive all-inclusive options, by far the best route.

I wanted to go for three nights but realized I would probably be spending a little bit out of pocket to do so. The Ultimate Rewards portal is powered by a third-party booking engine (Expedia, I believe) so you can see all the hotel listings, their amenities, the price in USD, and the point redemption.

I found several 4-star results that looked pretty good, but most of them would require me to spend all my points and $100-$300 extra to cover all three nights. I didn’t feel stellar about any of them, so I kept searching for a few days and decided to go for a weekend instead.

That’s crucial—give yourself time to plan. I’m big on finding and booking everything in one day since I’m usually traveling close-in (within the week), but having a couple days to weigh my options, read TripAdvisor reviews, and stare at my spreadsheet fantasizing helped a lot.

*Major key on weekend trips: pick the first flight there and the last (or second-to-last) flight back. We had basically all of Friday (because we landed at 11), Saturday, and Sunday, because we flew out around 6:30 p.m. It helped us make the most of a two-night excursion.

The magic of transferring points to partners

Right as I was about to book a 4-star resort with iffy food reviews, I noticed a resort that looked stunningly beautiful—and stunningly out of my price range. I’m sure you know where this is going.

The resort was listed at 44,000 points per night (about $550) in the Ultimate Rewards portal: the Hyatt Zilara Cancun. Someone had mentioned to me that, every once in a while, the travel partner (in this case, Hyatt) will list properties at a lower point value on their own site.

So I moseyed over to Hyatt’s site with very, very low hopes. Then I saw it—the Hyatt Zilara, listed at 25,000 points per night. In other words, I had enough points to cover two nights completely at 50,000 points total, vs. the 88,000 points it would cost in the Ultimate Rewards portal.

I was thrilled. I double- and triple-checked the rules, validating via The Points Guy that the transfer coefficient was 1:1, then I quickly transferred 50,000 points to Hyatt and booked the Zilara. As I was checking out, the Hyatt receipt said the final cost was $1,100 or 50,000 points.

It’s a pretty unique thrill to earn 50,000 points for doing your regular spending and being told that’s worth $680, but it's an entirely different thrill deriving an $1,100 value from those points—especially since (at the time of this writing) the Sapphire card has no annual fee the first year, effectively being cost-free ($95 after the first year—we'll get into the annual fee elsewhere).

Key takeaways

Always, always check the transfer partner (Chase's full list is here). Make sure you’re getting the best deal on Ultimate Rewards. You usually are, but every once in awhile, you'll find a gem.

The Sapphire Preferred card is literally a no-brainer if you have good credit and want a free vacation (*and you’re paying off all your cards every month with no debt!*).

All-inclusive resorts are an insane value — cutting corners to save money when you’re going to a country like Mexico will just downgrade your vacation. I have to say: staying in a 5-star resort with incredible food and incredible accommodations made me realize how, in a lot of cases, you get what you pay for (or rather, spend points on).

Lastly, and perhaps the best takeaway of all… money is only valuable insofar as it allows you to live the life you want to.

Taking a vacation with a loved one is the most valuable, memorable way I’ve ever found to spend time, and I’ve never regretted the money I’ve spent on travel — I can’t say the same about my Louis Vuitton bag, expensive jewelry or fancy clothes. I've made plenty of regrettable purchases in my past, and none of them were the experiences I had traveling.

Learn more about the Chase Sapphire Preferred card

Editor’s Note: Opinions expressed here are mine alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved, or otherwise endorsed by any of the entities included in the post.