Strategic Choices, major Hyatt changes, seize the high seas, and more [Week in Review]

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A week ago, Citi Thank You Rewards devalued transfers to Choice Privileges. That was a big bummer, but don’t sleep on Choice. The game isn’t over; we just need different strategic choices.

Yesterday, I used 20,000 Choice Privileges points per night to book a Choice Privileges property that had a cash rate of $550 per night. I didn’t transfer from Citi (maybe I would have considered a transfer from Wells Fargo, which still has a 1:2 transfer ratio to Choice, if I had those points to use). Instead, I purchased points from Choice Privileges. With the current sale, I spent a total of $463 to buy just over 60,000 points to cover a 3-night stay that would have cost $1,650 if booked with cash. That was a huge win! A week ago, it would have looked different; I’d have probably transferred 30,000 Citi points to cover that hotel. Rather than transfer 40,000 Citi ThankYou points with the new transfer ratio, I opted to use cash to purchase the points. Moving forward, my strategy for Choice is going to be a mixture of buying points when on sale (they often go on sale for an even better price) and shifting to earning Wells Fargo rewards. I’ll still hunt for great value with Choice, but my methodology will change.

My strategy has shifted with other programs, too. I’m far less interested in collecting Hilton points for high-end stays, but I am more interested than ever in collecting Hilton free night certificates, which remain uncapped (I used two certificates just last night). I am disappointed about Hyatt’s new award chart and category changes, but I remain confident that I’ll find value for different properties in the future.

The game changes all the time. It always has, and it will continue to develop and change. Those willing to adapt strategy can and will continue to find outsized value.

On the blog this week, read about major changes coming to World of Hyatt soon, the updated guide to booking Preferred Hotels, the ways to book free cruises in 2026, and a lot more.

a man in glasses looking at chess pieces

This week on the Frequent Miler blog…

World of Hyatt announces 2026 category changes. They’re not inspiring.

Hyatt Resort: Hyatt Regency Grand Cypress Sunset
Hyatt Regency Grand Cypress Orlando Florida USA will finally move beyond Category 4 on May 20th.

Hyatt’s 2026 category changes have arrived, and they aren’t pretty. I groaned out loud when I saw that the Hyatt Grand Cypress in Orlando has finally moved out of reach with a Category 1-4 free night certificate. Gone, too, are many US mattress run opportunities, with numerous Category 1 properties moving to Category 2. At the high end, a Regency property moves up to Category 8, and given the reach of the upper categories, the difference in price between current pricing and new peak pricing can be staggering. If you have any of these properties in mind, it’s time to book now while you can.

Mayday: Brutal new World of Hyatt chart launches May 20th

Award chart changes coming to World of Hyatt in May.

The other key piece of Hyatt news to drop yesterday was the announcement that the newly “enhanced” Hyatt award charts will launch on May 20th. Unfortunately, some properties are likely to increase in price by as much as 67% without even changing category. Fortunately, you have some advance notice: now is your chance to book and lock in current prices. Note that if you book a property that decreases in award cost on May 20th, you’ll get a one-time refund of the difference. If you book a property that increases in price, your reservation will be honored at the price you booked, so long as you don’t change (any changes will cause it to reprice). Make those speculative bookings for top-tier properties sooner rather than later.

Guide to booking Preferred Hotels with points (Updated)

How To Book Preferred Hotels with Points (Video)

Preferred Hotels and Resorts are a loose collection of boutique hotel properties, which can be booked with either Preferred Hotels I Prefer points or (in some cases) Choice Privileges points. Oddly, some hotels are bookable via one, but not the other, and others can be booked through either program. With the recent change to transfer ratios from Citi ThankYou Rewards, Greg took on the significant task of updating the data and map to indicate which program you should use to book.

“Free” Cruise match opportunities still exist in 2026

a man taking a selfie on a cruise ship

It is hard to believe that we first wrote about casino matching for free cruises almost five years ago. Many readers were able to take advantage of one free cruise offer after another for years, and my family has enjoyed a cumulative total of several months at sea over the past couple of years. While the free cruise tide has ebbed some in recent years, there are still a number of opportunities available to those who are interested in hitting up the high seas. This post includes most of the current opportunities to get free cruises through land-based matches, direct casino line matches, and old-fashioned gambling.

Cruising for free | Frequent Miler on the Air Ep355 | 4-23-26

Cruising for free

On this week’s Frequent Miler on the Air, Greg and I discussed many of those methods to earn free cruises in 2026, and a little bit about the strategies that can be employed to earn status and free cruises moving into the future. We also discuss our differing strategies for using points to book events, an elevated and easy-to-earn $230 bonus with Melio, our opinions about Google Hotels adding price tracking, and a lot more.

How to avoid airline surcharges | Coffee Break Ep102 | 4-21-26

How to avoid airline surcharges (blog)

With fuel costs skyrocketing, we have recently seen several airlines increase award surcharges in recent weeks. Unfortunately, that is a trend that is likely here to stay. The good news is that there are many ways around carrier-imposed surcharges for those who leverage the power of airline partnerships. Bummed by the recent increase in award surcharges on Air France / KLM? You might be able to book the same award via Virgin Atlantic for less, or eliminate the surcharges altogether if you book via Japan Airlines Mileage Bank. On this week’s Coffee Break, which we recorded in front of a live audience at the Points Travel Festival Toronto after taking topic suggestions from the crowd, we discuss the many ways to avoid increasing award surcharges.

Pointsevents, an awesome tool to find experiences bookable with points

If you are interested in trading your points for experiences, you’ll want to bookmark Pointsevents.com (or perhaps PointAuctions.com, which was mentioned in the comments by a reader). I have recently spent a good deal of time combing through different sites to find auctions/events that might be of interest, so I really appreciate a site that collates all that information. I also found auctions that I wouldn’t have otherwise seen, as I hadn’t realized that Accor had auctions, and I saw some events that I never would have hunted for without an easily sortable and filterable list. I will definitely be making use of this.

Google Hotels adds price tracking. Save money by tracking and re-booking / best price guarantees

I am thrilled to see Google Hotels add price tracking for individual properties. I almost always make flexible hotel bookings that can be cancelled and/or changed. The ability to easily track the price of a property I have booked and be alerted when there is a chance is a huge benefit that could save me a ton of money over the course of a year. And with many hotel programs now pricing awards dynamically, I imagine it could also be easy to identify opportunities to rebook award stays as prices change.

Chase Sapphire Reserve® vs Sapphire Preferred®

a blue and black credit cards

Which card is right for you largely comes down to how you feel about the Sapphire Reserve card’s coupon credits. Personally, I feel lukewarm about those credits at best, which makes me underwhelmed with the idea of keeping the card long-term. I may end up hanging on to it since I blog about credit cards, but I think most folks are likely to be better off with the Preferred.

An unfortunate Capital One Shopping by-product: Slow Gmail in Chrome

Stephen noticed something strangeabout the Capital One Shopping extension: it seems to have slowed down Gmail in the browser where he has the extension installed. I haven’t noticed that problem at all, though it occurs to me that the reason might be that I don’t use Gmail in the Chrome profile where I have the extension installed except if I am clicking through a targeted email offer (which I’ve usually noticed while browsing my email on my phone or in another browser). I have a separate Chrome profile that I only use for Capital One Shopping, where I’ll click around only those sites where I hope to trigger a targeted shopping offer. I’m therefore not using email very much in that browser and may not have noticed this issue if Stephen hadn’t identified it.

Amex Airline Fee Reimbursements. What still works?

a plane flying over money

Cue up the funeral march; using Amex airline fee credits to buy Delta airfare appears to be dead. It was previously possible to split payment between a gift card or flight credit and an Amex Platinum card, with the portion on the Platinum card inadvertently triggering an airline incidental fee credit. Unfortunately, that no longer works to trigger Platinum card incidental fee credits. In fairness, this was never an intended use of the credit anyway, but it is nonetheless a big disappointment for those who have been using their credits this way for years.

JetBlue TrueBlue Complete Guide (2026)

JetBlue Airbus A220 airplane

We’ve updated our JetBlue TrueBlue Complete Guide to reflect numerous changes over the past year, including the introduction of some phases of the Blue Sky partnership with United, the launch of Points on Repeat subscription options, the ending of some airline partnerships, and more.

What is a mattress run? An explanation & why and how you might want to do it

a group of men carrying a mattress

One of our occasional podcast segments is called “Mattress Running the Numbers”, where we’ll sometimes talk about whether a promotion is worthwhile just to trigger the payout. The naming convention comes from the idea of a mattress run: when you book a hotel even though you don’t really need to stay there, just so you can trigger a promotion, elite status, or something else. In this beginner series post, Stephen explains in more detail the purpose and why you might take one on.

How to use AwardTool to search for award flights (Video)

How to use AwardTool to search for award flights (2)

AwardTool can be a powerful search tool for finding great flight awards (in fact, I was just now toggling between this window and one where I was running an award search!). However, some of the features may not seem obvious or intuitive without a little explanation, so Greg and I made this video to show you the key things you need to know about this powerful tool.

Best ways to get to Europe with points and miles (2026)

a map of europe with different colored areas

If you’re looking to get to Europe on points and miles, our guide for the best ways to get to Europe with your rewards can help you figure out some of your best options. With surcharges and award charts constantly changing, Tim recently took the time to fully update this guide for 2026.


That’s it for this week at Frequent Miler. Keep an eye on this week’s last chance deals to grab those ending in April before they’re gone.

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Tom

Speaking of strategic choices, what are some alternative approaches to travel protections if one is done with the Chase ecosystem? Thanks.