I’ve been running on low sleep all week, including a couple of nights with only about 2 hours of sleep. You could say that I’m in training for our upcoming Frequent Miler Team challenge, 100K Vacay. Those who know how I like to travel understand that I enjoy being on the move and don’t enjoy wasting time on sleep when there’s something better I could be doing (but fear not, I do love to sleep when I have the time!). My sleepless nights this week have been consumed by trying to plan the most epic 100K Vacay possible.
This year’s team challenge has turned out to be more challenging than I anticipated. I’m finding no shortage of great flight deals — the world has truly felt like my oyster in terms of where I can go for a reasonable number of miles. And I’ve discovered some hotels that look like awesome deals — with cash. If I could pay cash for my stays, my 100K Vacay would look a lot different! The rule that lodging must be paid using points — and the subsequent requirement to get good value for points — means that the real challenge for me has been not in finding destinations where I’d like to go but rather finding destinations where the cash price of lodging is high and the points price is low. That has certainly made the challenge more interesting for me in the planning phase! That said, I am very excited to have landed on a couple of stellar deals like this one that I shared yesterday that could help make a pretty wild vacation happen for a very reasonable cost. More to come in the next couple of weeks as we prepare and then take off on the trips we’ve been planning.
Elsewhere on the blog this week, we have an updated comparison of the best credit card travel protections, a review of a a great family resort in Orlando, and more.
This week on the Frequent Miler blog…
Announcing the 100K Vacay team Challenge! [Mark your calendar]
While we initially announced our 2025 Frequent Miler team challenge a few months ago, this initial announcement post has now been updated with specifics. Most importantly, it now includes our travel window dates, with Greg’s trip kicking off on September 25th and the rest of us set to travel during the first week of October. How will Greg set the bar and what are our strategies to clear it? Read on for more on that with the posts below.
My 100K Vacay bar-setting strategy (Greg’s Journal)
In this post, Greg lays out his strategy to set the bar for the competition. On this week’s live Ask Us Anything on Youtube, Greg shared that since Hyatt is generally accepted as the core strength of his currency, Chase Ultimate Rewards points, he knew that he had to lean on Hyatt for lodging. That tidbit doesn’t really narrow things down, though. With so many great low-category properties around the world, Hyatt gives Greg a lot of opportunity for quite a trip.
My 100K Vacay Strata-gy with Citi ThankYou Points (Tim’s Journal)
With arguably the best set of multiple hotel transfer partners, Tim enjoys almost an embarrassment of riches on the lodging side. Will he go with Choice Privileges at 1:2, find an outstanding Preferred Hotels property at a 1:4 transfer ratio, or take advantage of that 25% transfer bonus to Leading Hotels of the World? I actually haven’t read my competitors’ prep posts because I don’t want their decisions to influence my own, so you’ll have to read Tim’s post to find out!
100K Vacay: Resetting the odds due to transfer bonuses | Frequent Miler on the Air Ep322 | 9-5-25 | Podcast
When we first decided on our 100K Vacay team challenge, we knew that transfer bonuses would be an integral part of the game. Since we were capping ourselves at 100K specific transferable points and banning ourselves from buying additional points with our cash budget, the only way to get more points was by taking advantage of a transfer bonus. We are closing in on our travel window (which starts in a few weeks!), so on this week’s Frequent Miler on the Air, Greg and I discuss which transfer bonuses each contestant has had in play and whether we think that has changed the game in terms of who has the advantages.
Preparing for the Sapphire Reserve® 10/26 transition | Coffee Break Ep69 | 9-2-25 | Podcast
If you’ve been a Sapphire Reserve cardholder since before June 23, 2025, you are grandfathered into some benefits for a period of time. In order to ensure the maximum floor redemption value of your Ultimate Rewards points, you’ll want to get them onto your Sapphire Reserve card before 10/26. On this week’s Coffee Break podcast, Greg and I discuss everything you need to do, and which folks do not need to do anything at all.
A wish list of ultra-premium credit card features (on Nick’s mind)
With the latest ultra-premium credit card refresh coming around the corner, a reader asked what we think an issuer has to do to remain competitive in the ultra-premium card space. While we have seen a lot of issuers refresh (or launch) ultra-premium credit cards this year, I think there is room for a lot more innovation. I wrote this post as I thought of the core things that I would like to see on ultra-premium credit cards in the future. To be clear, I don’t think we’ll see any of this when the Platinum cards refresh soon, but I hope that we see some stuff like it on future cards/refreshes.
Guide to Ultra-Premium Credit Card Travel Protections
At the top of my wish list is for a card to have industry-leading credit card travel protections. I don’t plan for problems to happen, but neither do I want to be on the hook for a large chunk of change out of pocket when they do. I want to book travel with a card that is going to cover my costs when things go sideways. Greg has updated his post comparing the best credit card travel protections to include the latest cards added to the market.
JW Marriott Orlando, Grande Lakes: Nick’s new favorite Orlando Resort
My family spent a couple of nights at the JW Marriott Orlando, Grande Lakes. This was despite some objection from my wife, who (before our stay) preferred to return to family-favorite Hyatt Regency Grand Cypress. We left the JW Marriott a little sad, knowing that we may not make it back to that Hyatt Regency for a long time; the JW Marriott was just a great place to spend a few days as a family. My kids could do two of the three water slides, the adventure park was a lot of fun, the lazy river is huge, there are a number of dining options, and there was plenty more going on to keep us occupied for days. Truth be told, we’ll still probably end up at the Hyatt Regency Grand Cypress when traveling during peak times both because of the very reasonable award price and the ability to confirm a suite, but I left the JW Marriott ready to book five nights at the JW during next year’s shoulder season. A couple of readers pointed out that guests at the nearby Marriott Lakeshore Reserve, a vacation club property where you can often get a 2-bedroom townhouse for about the same cost as a regular room at the JW, get access to the facilities (including the pool / waterslides) at the JW Marriott. That could be a great option for times when we crave more space.
Separately, as a reminder, you should bookmark these posts that are updated regularly to remain current sources of the best promotions available:
- Best Credit Card Offers for September 2025
- Current point transfer bonuses for September 2025
- Current Hotel Promotions for September 2025
That’s it for this week at Frequent Miler. As always, keep an eye on this week’s last chance deals.
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