My 100K Vacay Strata-gy with Citi ThankYou Points (Tim’s Journal)

It’s September 1st, which means we’re one month to the day from the beginning of the 2025 Frequent Miler Annual Challenge. This year, we’re calling it “100K Vacay.”

The goal is for us to compete to see who can plan the best vacation using no more than 100,000 points and $1,000 in cash. All of our lodging and our international flights have to be paid for entirely in points; we can only use cash for activities, food, and local/regional transport. Each contestant can only use one transferable currency: Nick gets Amex Membership Rewards, Stephen gets Capital One Miles, and I’m using Citi ThankYou Rewards.

Carrie and Greg will judge between the three contestants, awarding points for style, affordability, unique leverage (i.e., the use of unique aspects of each transferable points currency), and applicability (i.e., uses of points that are of use to many people).

All three of us have been planning furiously (or in some cases, “more relaxedly”), but we’re a month out, so it’s getting to be crunch time. After a couple of months of surveying the pointscape and mulling over the task of creating the perfect 100K vacation, I’m seeing the faintest outline of a “Strata-gy” begin to appear.

What is the 100K Vacay challenge? This fall, Nick, Stephen, and Tim have each picked a different transferable points currency they think can compete with Greg’s 100K Chase Ultimate Rewards points, each trying to beat Greg’s 100K Vacay with one of their own. In the end, we’ll find out who can book the most amazing 100K point vacation!

September 1st, 2025 (one month before the start of the challenge)

My approach to the 100k Vacay challenge

I tend to be more of a “spirit” vs the “letter” of the law kind of guy; I imagine many points and milers are. The last challenge that I participated in, Flying by the Seat of our Points, was focused on last-minute travel. Which contestant would better manage jetting across the globe in style when they only had 24 hours’ notice to get there?

As part of that challenge, Greg asked us to write a post saying how we were preparing, and my first thought was, “Is it part of the spirit of a ‘last-minute travel challenge’ to prepare?” I thought not.

So, I spent some time thinking about what the conditions would be for me to play the game as though I actually had found out that I needed to be somewhere in 24 hours, then go from there. You can read what I how decided to do that here, but I had a lot of fun on the challenge by not reading the fine print terms and conditions, and instead going by what I thought most honored the “spirit” of the challenge.

This time around, I asked myself, “What is a 100k Vacay?”

What is a 100k vacation anyway?

When the FM Team was first discussing this challenge, we were debating between two different names: “100k Vacay” or “100k Getaway.” We eventually decided on the former, the idea being that it was more impressive (and difficult) to plan an entire vacation than a simple “getaway.” That’s also part of the reason that we chose to only give each contestant one week to do all of their travel, since many people don’t have the luxury to choose exactly when their vacation days fall.

But, I’m still a little fixated on the whole “vacation” word. What do our trips need to look like for the average Greg or Carrie to be convinced that we pulled off a killer vacay with Style, Affordability, Leverage, and Broad Applicability?

I’ve got some ideas, based on that “broad applicability” goal for this challenge.

It needs to be at least five nights

Officially, in order for our trips to pass muster, they need to be at least three nights. However, what would you say if I were to tell you that I was going on vacation for three days?

Probably something along the lines of, “Not a very long vacation, is it?” You’d be right.

Three nights are a long weekend. A getaway. A bank holiday. But, not a vacation. So, for my trip, I’m setting myself a goal to travel (and lodge) for a minimum of five nights.

It needs to feature at least two popular destinations.

Our resources are limited to 100k points and $1,000. My natural first thought was, “Where can I go where the dollar is strong and where my points will go the furthest?”

However, I quickly decided against doing that.

A big value of this contest is broad applicability, and many of those budget destinations just aren’t popular or easy to get to for folks in North America, especially in a week’s time. Instead, I want to concentrate on the most sought-after destinations for North Americans.

In order to cover more area (and make it more challenging), I want to visit at least two of those countries. The additional transit will put more strain on my modest resources, but will hopefully show off even more interesting places that can be visited on the cheap.

I need to get at least $4,000 in value from my points

It’s easy to do a cheap vacation to an inexpensive destination, but what about getting value in notoriously expensive ones?

Now that’s a bit more challenging.

Asher & Lyric regularly publishes a “Budget Travel Index” which breaks down the costs of a 5-night trip to the 100 most popular tourist destinations in the world. It then grades them from “A+” to “F,” based on affordability.

There are currently 17 countries that have an “F” grade, and that’s where I want to concentrate my effort. If you average the Asher & Lyric trip cost among all 17 of them, it leads to a total of ~$5,000 for an entire trip. That seems like a good benchmark.

I want to visit at least two of those “F” countries, and since I have $1,000 in cash to work with, I need to get at least $4,000 in value out of my points in order to hit that $5K average. That works out to an average redemption value of 4 cents per point.

Now, this is starting to sound like a challenge!

It should have elite perks without needing elite status

Every time we do a challenge, we have a debate: “Should we show off elite perks?”

All of us on the team have elite status in many hotel and airline programs, and lounge access from credit cards. But that’s not most people’s situation. The more common scenario is maybe one or two hotel statuses from credit cards, or a low-to-mid-level hotel status.

In this case, I’m supposed to show what can be done with 100,000 points only and make it as broadly applicable as possible, so I’m not going to take advantage of any elite statuses that I have, unless an average reader of Frequent Miler could have gotten the same status without having to travel or spend any money.

That doesn’t mean that I’m not going to bling out, however. I want included breakfast! Hotel suites! Free snacks and welcome amenities! My challenge is to show it can be done, even if you’re not a Hyatt Globalist or a Hilton Diamond.

It needs to be comfortable

There are a lot of ways to travel around the world. The older I get and the more joints I replace, the less comfortable many of them are.

For instance, I can’t sleep in economy airplane seats, and sleep comes at a premium during these challenges. Nick and Stephen have an incredible superpower, where they can almost instantly snooze away the moment they sit down in a plane, train, or ox-drawn cart. I’m the exact opposite. I have an occupationally inconvenient inability to fall asleep in any sort of upright position, regardless of how tired I am.

Because of this, I’m going to make a solemn vow: I will not darken the economy cabin of a single overnight flight.

Why I chose Citi ThankYou Points for 100k Vacay

I’ve long been a huge fan of Citi ThankYou Points, despite their historical reputation as the homely black sheep of transferable currencies (although that’s changing a lot now that Citi has a new premium card and transfers 1:1 to American Airlines). Chase and Amex boasted more well-known transfer partners and bigger welcome offers, the combination of which has made them much more sexy in the eyes of most points-huggers.

Citi’s reputation was so bad that when we first started talking about each contestant choosing a single rewards currency for this challenge, a certain team-member-who-won’t-be-named exclaimed, “That would be fun, but who would take Citi Points and only get 1.6 cents each for hotels!?” I knew I had to defend my favorite, underappreciated points’ besmirched honor, so I volunteered. Given my goals, I’m very pleased about that choice.

I think that I’ll be able to squeeze a “Strata-spheric” amount of fun using my stash of 100k ThankYou Points. Here are a few reasons why.

Citi ThankYou Rewards has several unique hotel partnerships that are excellent

I’ve said for some time that I think Citi’s hotel partners are the best of any other currency, with the exception of Chase Ultimate Rewards’ ability to transfer 1:1 to Hyatt. However, it gets much less attention because the only big brands it has are Choice Privileges and Wyndham Rewards. But there’s plenty of opportunity here.

Choice has some excellent properties overseas, and Citi points transfer 1:2, making many interesting locations available for 5-15k points. Transfers to Preferred Hotels are 1:4, meaning excellent redemptions can start at ~7.5k Citi points per night. Leading Hotels of the World has some drool-worthy hotels and averages around 1.6-1.8 cents per point in value (or better with a transfer bonus), while Wyndham transfers to both Cottages.com and Vacasa can be a marvelous use of points for vacation rentals.

Several of these programs allow you to book multiple room types with points, sometimes at the same price as a standard room, a feature that will come in very handy when trying to show accessible bling. To my mind, Citi’s lodging partners are my biggest advantage over Nick and Stephen and the biggest reason that I wanted to take ThankYou Points for a whirl.

What Citi lacks in transfer bonus quantity, it makes up for in quality

Citi has a fraction of the annual transfer bonuses that Chase and Amex strut out. However, they usually tend to do at least one per year for many of their partners. In this challenge, we can take advantage of transfer bonuses in order to stay under 100K, the one caveat being that they have to happen during the “planning phase” of our trip (essentially April-October).

Here’s what I’ve had access to so far:

• 25% transfer bonus to Avianca LifeMiles
• 30% transfer bonus to Virgin Atlantic Flying Club
• 30% transfer bonus to Qatar Privilege Club Avios
• 25% transfer bonus to Wyndham
• 20% transfer bonus to Air France KLM Flying Blue
• 50% transfer bonus to Accor Live Limitless
• 25% transfer bonus to Leading Hotels of the World

Now, we don’t see a lot of the 35-40% numbers that Nick gets with Amex, or that Greg can take advantage of with Chase during his “setting the example” trip. However, I’ve still had the opportunity to take advantage of bonuses on Star Alliance (via Avianca), SkyTeam (via Virgin and Flying Blue ), and oneworld (via Avios) flights. I may have to be a bit more creative, but hey, you can’t spell “creative” without eat, and I love eating.

Even without American, Citi’s airline partners aren’t that bad

Now that Citi transfers to American Airlines 1:1, they’ve become much more desirable for air travel. However, when we picked these currencies, none of us knew that transfers to AA would be possible before the challenge. Due to that, and in the interest of fairness, I’m not going to be transferring any points to AA.

That said, even without AA, there are some excellent partners. I’ve used EVA Air’s points a few times to go between the US and Asia, and the combination of price and business class availability from Seattle is unbeatable. However, I don’t know that I’ll have the budget for a 75k lie-flat flight to Asia on this trip.

Flying Blue can offer some surprising value between Europe and other regions, especially when using its monthly Promo Rewards. Qatar gives me access to the entire coterie of Avios programs, while Virgin Atlantic opens up decent pricing on some SkyTeam awards along with rock-bottom prices on flights between the US and Europe (albeit with significant surcharges). Avianca gets a deservedly bad rap for the serpentine phone tree and maze of bad IT that it calls “customer service,” but it still has an enviable list of sweet spots on Star Alliance awards.

Without AA, I’m certainly not going to argue that Citi has the best airline partners. That would probably be Amex Membership Rewards. But I think there’s enough here to keep me competitive, especially when combined with Citi’s lodging partners.

Final Thoughts

Now, those who’ve already read Nick’s and Stephen’s strategy posts will notice that my approach is a little different. My hope is that my dedication to embracing the spirit of planning a 100K Vacay while maximizing Style, Affordability, Unique Leverage, and Broad Applicability will give me some extra “Strata-s” points in the eyes of our two esteemed judges (Greg and Carrie). After all, they’re a tough crowd.

Regardless of who emerges with the (non-existent) challenge crown, I think this year will be a fun one and hopefully broaden all of our notions of what’s possible with 100,000 points

Join Team Tim (Subscribe to this Post)

When the challenge begins, I’ll be updating this post regularly. This will be my daily journal where I’ll document my plans, successes, and failures as I go along. I welcome any help that I can get and would love to hear any ideas that you’d like to share with me!

Perhaps you’ll know a particularly great sweet-spot award or hotel deal that I can take advantage of with my Citi Points. Maybe you’ll have other advice for one of my destinations: how to get around cheaply, where to eat yummy food at delicious prices, or free and low-cost activities that will make Nick and Stephen jealous.

If you’re interested in helping me, then commenting at the bottom of this post is how to do it. Also, by subscribing to this post’s comments, you’ll get emailed whenever someone (including me) adds a comment.

Each of the contestants will have a post like this one where everyone is welcome to participate by making suggestions in the comments. You can pick a single person to follow (Nick, Stephen, or me), or you can click back and forth and help us all. Either way, we’re eager to hear from you!

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