Stephen’s Speculation: Who’s Greg’s Travel Companion For 3 Cards, 3 Continents?


Greg’s written a few posts about his plans for 3 Cards, 3 Continents. In a recent post he shared that he’ll be bringing along a travel companion for the trip, but he hadn’t shared who that’ll be.

What is 3 Cards, 3 Continents? Frequent Miler loves creating fun and competitive team challenges. This year Greg, Nick, and Stephen are competing to book the most amazing 3-continent dream-trip using 3 credit card welcome bonuses.

This morning Greg cut in half the list of people who could potentially be joining him as he repeatedly referred to she and her. So we now know that his travel companion will be female, but he still isn’t disclosing who it’ll be.

I’ve been speculating recently in our Frequent Miler staff Slack chat as to who will be traveling with Greg – here are my guesses.

3 Cards 3 Continents Greg's Travel Companion Speculation
Apparently it’s my elbow that’s doing the deep thinking

An Ana

Greg’s round-the-world trip is primarily being booked via ANA, so perhaps he’s continuing that theme by traveling with someone called Ana.

The new movie about Marilyn Monroe – Blonde – comes out in late September, so maybe Ana de Armas will be joining Greg a couple of weeks before that as a way to travel the world to promote the new movie.


Greg’s cat Stripey frequently makes an appearance during Frequent Miler team meetings. In French, “the cat” is “la chat” rather than “le chat” which makes it feminine, so will Greg’s companion be feline good by being picked as his travel partner?


Carrie takes care of much of our social media content and we’ll likely have a lot of that during the 3 Cards, 3 Continents trip. Perhaps Greg has agreed to book a RTW ticket for her to join him, thereby ensuring he gets favorable coverage on Instagram, Facebook, etc.

a woman sitting in a chair with headphones on
Will Carrie be sitting up front during Greg’s trip?


Although Greg ended up with just enough Membership Rewards to be able to book an ANA round-the-world trip, it might be that he doesn’t have enough to book what he truly wants for his trip.

If that’s the case, his companion might be Cher so that she can turn back time and he can repick his cards. Also, imagine how amazing all of Greg’s costume changes during the trip would be.

Annie Leibovitz

If Greg doesn’t pick Carrie to ensure his social media game is particularly strong, Annie Leibovitz will be a good alternative so that he has the most glamorous shots to post.

Claire Fraser

This one’s for the Outlander fans. I don’t know if this would work out because I feel like not everyone can pass through Craigh na Dun based on what I’ve caught when my wife’s had the show on, but if Greg was able to pass through the stones with Claire Fraser to go back in time, perhaps they can go back far enough in time to just after Pangea started breaking apart. That way he could wade from continent to continent and pick up the three continents he needs in a matter of minutes. Go back too far though and he’ll be stuck with 3 Cards 1 Continent

My Wife And/Or Nick’s Wife

Will Greg play dirty? Maybe he’s planning on taking one of our wives on his trip, but then threatens to abandon them in the middle of nowhere unless we sabotage our own trip. It’s unlikely, but maybe my wife’s agreed to go along with his plan for not deciding to bring her along on my trip.

Iowa's largest frying pan
Greg’s trip will likely be more exciting than visiting Iowa’s Largest Frying Pan

Greg’s Mom

I think the most realistic guess is that Greg will be bringing his mom along for his round-the-world trip. Not only will that earn him lots of son points, but it should pick him up quite a few reader votes for being such a thoughtful son.

Your Guesses

Do you have any thoughts on who Greg might being along with him for 3 Cards, 3 Continents? Let us know your guesses in the comments below.

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He is taking Big Ern Mckracken, professional Bowler, from Reno, Nv.

Big Ern Mckracken

Sam I told you not to spill the beans, Greg and I have BIG plans for this trip


Hmmm I was thinking the Wife’s best friend or Better yet her Sister. A keep it in the Family Affair ..
A $$$ maker for FM..

Last edited 1 year ago by Cavedweller
Big Ern Mckracken

You have got to get out of the Cave more often.What does this have to do with the price of tea in China and me, Big Ern Mckracken?


Through the first half of his post I thought it was likely Stephan of Rapid Travel Chai (they’ve travelled several times before, Stephan has presumably been mostly grounded in the PNW), then I though there was maybe a 20% chance it was Drew of Travel is Free (now locked in a TPG dungeon somewhere coding the TPG app), they have also travelled together before, through Namibia.

..and then he started dropping gender pronouns…

I thought Carrie but, employee or not, it’s a bit weird to travel with another man’s wife, IMHO.

So my money is Frequent Mommy Miler.


I hope it j
is his mama. Unless he picked me of course!


I am guessing it is Greg’s Mom. Greg mentioned paying out of his pocket for his mysterious travel companion, so it must be a family member.


Good Thing and Proper can she still travel ?


Greg mentioned in his post this morning that the person was nominated by Mrs. Miler. So definitely NOT Ana de Armas.

I’m guessing that you’re right and it’s the dowager Miler, but of course Mrs Miler could have nominated herself.


You never know she may like the Pool Boy better and wants to get out with Everything. What did Trump’s first wife say ” Don’t get Even, Get Everything !! ” Fine statement by a Woman..
V Bernie


I vote for the cat! Sure there was a popular blog about a guy bicycling around the world with his cat and sleeping in a tent but what about premium travel? Can I take my cat into the Centurion lounge? How to prevent the sofa in your suite being used as a scratching post? I’d travel to Toronto to hear Greg speak on this subject.


Only if you use a cat 1-4 certificate (up to four felines) or a cat 1-7 (up to seven).

Tim Steinke

That’s the perfect point, Larry!


Very clever post. You all are so much fun!

Greg The Frequent Miler

I should have consulted with Stephen before picking my travel companion. He has some great ideas.


Sickness is well known in the UK too as in the Royals. May God Save the Queen..V Bernie

Last edited 1 year ago by Cavedweller

1) You know the Wife picked the She but that doesn’t mean She isn’t the She.

2) How about too if the She can’t make it (Legal Things) and the Wife (She) goes in her place at the last minute ??

That’s not She impossible.

Meanwhile Click Bait $$$….V Bernie

Last edited 1 year ago by Cavedweller

An Ana got a lol out of me


Gotta love the Cher idea to “turn back time”, very creative Stephen. I’m not sure if Greg has any sisters, but maybe that is an idea too.


The question should Be does the sister have GF’s Hmmm.V Bernie