Why Stephen chose Capital One Miles for 100K Vacay

Our 100K Vacay challenge is coming up this fall, so it’s time to share why I chose Capital One miles for it as my reasoning might not be what you’d expect.

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!

I’m starting in the US

My wife and I moved to the UK a few months ago. When we (the Frequent Miler team) were initially planning the challenge and deciding on the rules, one of the things we discussed was where I should start from. The rest of the team thought it would be OK for me to start in the UK. In some ways, that could make the challenge more interesting as I’d be able to showcase what could be done with 100,000 miles and $1,000 when starting from the UK rather than the US, potentially finding some different sweet spots.

However, I wasn’t overly keen on this. I figured it could be seen as having an advantage of sorts seeing as the UK is closer to far more countries than the US is. The applicability of my trip for readers – another important factor in how the challenge will be scored – would also be questionable. The vast majority of Frequent Miler readers are based in the US, so a vacation that sets off from the UK likely wouldn’t be quite as helpful.

I’ll therefore be flying back to the US for the start of 100K Vacay so that we’re all on a level playing field.

I want need to win

Other than the Party of 5 challenge where the team of Carrie and I came joint first versus the team of Nick and Tim, I’m the only member of the Frequent Miler team who hasn’t won one of our annual challenges. I came second in both 40K to Faraway and Million Mile Madness, but I want to win. I need to win!

That’s why I chose what’s arguably the worst points currency for the purposes of this year’s challenge – Capital One miles.

Why Capital One is the worst transferable currency (for this challenge)

As a reminder, we have 100,000 points and $1,000 to book an amazing vacation. We have to return to our initial departure point and include at least three nights of accommodation at our destination.

As a result, one of the main focuses of this challenge will be on accommodation and that’s where Capital One falls behind compared to the other transferable currencies being used in this challenge.

Chase Ultimate Rewards has Hyatt.

Citi ThankYou has Choice Privileges as a 1:2 transfer partner and Preferred Hotels at a 1:4 rate. In the last 12 months, Citi has offered transfer bonuses to Accor, Wyndham (twice) and Leading Hotels of the World (twice).

Amex Membership Rewards meanwhile has Hilton at 1:2 and Marriott at 1:1. In the past 12 months, Hilton has also offered three transfer bonuses to Hilton and three to Marriott.

n.b. those are all the more notable hotel transfer partners; it’s not a comprehensive list.

By comparison, Capital One is mediocre. You can transfer to Wyndham on a 1:1 basis. You can transfer to Choice on a 1:1 basis (which is only half as good as Citi). And you can transfer to Accor on a 1,000:500 basis. If you’re not familiar with the Accor Live Limitless program, each point is worth a fixed 2 Euro cents, so 1,000 Capital One miles are worth ~$11.63 when converted to US dollars.

Considering Wyndham and Choice points frequently go on sale for far less than a penny apiece, it’s therefore much better to either pay cash for your stay or buy points than it is to transfer Capital One miles to either of those programs. The thing is, we can’t buy points for this challenge – we can only use our transferable currency. That leaves Accor as the only hotel program where it might ordinarily make sense to transfer points; even then it’s simply impossible to get outsized value due to the fixed value nature of the points.

Capital One also rarely offers transfer bonuses to any partner. Over the course of the past year, Capital One has offered a grand total of 6 transfer bonuses, none of which have been to hotel partners. Compare that to Citi (17) and Amex (23) and you can see that I’m at a severe disadvantage for being able to maximize the value of my 100K miles.

That means that having Accor, Choice and Wyndham to play with (at non-favorable transfer rates) and few chances to get better-than-normal transfer ratios to airline partners due to a dearth of transfer bonuses should give me a greater chance to impress as I’ll be working within much stricter confines.

What I won’t be doing

We’re all playing our cards close to our chest at the moment, so at the moment I can’t share where I’ll be visiting. I can share where I won’t be visiting though. Sort of.

During our challenge dates there’s a fun event happening in the US. I can’t share which one just yet because then you’ll know our challenge dates and we’re not disclosing those right now. As you might expect, the cost of accommodation in this city jumps up during the event dates (it lasts for more than one day). I initially thought it could be fun to show how to spend at least three days in that city to showcase the event and other things you could do in that location.

However, I ultimately decided against that for a couple of reasons. One is that I’ve been there before and so it didn’t feel like it’d be as much of a challenge. It’s also in the US and, while many people might be interested in what could be done as a 100K Vacay in the US, staying domestically would almost guarantee that I wouldn’t win the challenge. So overseas it is.

I have a theme

For the 3 Cards, 3 Continents challenge, I decided to go with a theme as I wanted to fly both the world’s shortest and the world’s longest scheduled flights. For 100K Vacay, I’m going with a completely different type of theme, but it’s one that’ll also be a lot of fun.

My theme this time isn’t aviation or accommodation based, but will instead relate to the activities I’ll be doing. For a lot of people, how you fly and the hotel you stay in isn’t as important as what you’ll actually be doing at your destination. I’ve still put a lot of thought into my flight and accommodation choices, but having fun on this trip is what I’ll be trying to showcase even more.

My theme isn’t something that every single reader would pick for themselves, but despite that I think there are quite a lot of elements to it that you’d enjoy nonetheless just for the sheer experience of it.

I’ll have energy!

I’m also confident that my trip during this year’s challenge will be more interesting activities-wise compared to past challenges simply because I’ll have enough energy to do stuff!

I’m not trying to make excuses, but for the last few challenges I’ve been exhausted. My wife and I finished our 50 state road trip at the end of 2024, having moved to a different city pretty much every single week for 7 years. For Million Mile Madness, we were finishing up state #49 and getting ready for our final state – Hawaii. Between that and all the economy flights on that challenge, I was too tired to do as many activities between flights as Nick managed to cram in.

For Party of 5, I got sick during the last few days which meant getting drenched at Iguazu Falls wasn’t as fun as it should’ve been. As for 3 Cards, 3 Continents, we’d just gotten back from a trip to Europe with friends where we’d spent two weeks moving pretty much every other day.

By the time we set off on our 100K Vacay trips though, I should be fully refreshed. After moving to the UK in April, we finally found a place to live and moved in at the beginning of June. This is the first time we’ve had a home in almost 8 years, so it’s nice to be settled somewhere for a little while and not have to expend the mental energy of constantly finding new hotels to stay in, research things to do in each new place, pack and unpack everything we own, etc.

Also, just a few days ago I was diagnosed with a medical condition. It’s not a serious condition when treated and I’ve now got medication for it, but one of its symptoms is lethargy. Based on my family history (which I just discovered), I’ve likely had it for quite a few years, so that would also go some way to explaining why I’ve not always had as much energy on these challenges as I would’ve liked.

The good thing is that I’m confident that I’ll now be raring to go this fall when Tim, Nick and I all set off.

There’s something else…

I also have a little trick up my sleeve for this challenge which will make it even more interesting. Once again, it’s not something I can disclose now, but it’ll definitely enhance my trip and I can’t wait until I set off so that I can reveal it.

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