Tim & Nick predict: What we think Stephen and Carrie will do


The Party of 5 Team Challenge is right around the corner and both teams have plenty of questions about what’s ahead. Foremost among them is “where are we going?”

While our other challenges have highlighted the wild and amazing things a person can do with miles and points, this challenge seeks to showcase what incredible things might be possible for a whole family of 5. This time all five of us are traveling together for two weeks. But to keep that fun element of competition, we’ve divided into two teams. Stephen and Carrie (Team TYO) have planned out the first 5 days of this “family vacation”, based out of Tokyo, while Nick and Tim (Team SFO) have planned out the next 5 days, based out of San Francisco. Of course…we’re not telling each other what we’ve got planned. We’ve planned itineraries which we hope will impress and delight the whole “family”, but we’re paying special attention to the head of our family – Greg – who will serve as the judge, jury and referee, rewarding bonus points along the way.

For a more thorough recap, and a reminder about how we came up with the launch-points for each team, make sure to re-read this post.

Team Tokyo (TYO) took a stab yesterday at guessing where Nick and I would be whisking them off to once we return to the Western Hemisphere. It should be known that we’ve laid plenty of hint-laden bread crumbs along the way for TYO. Almost a complete road map, really. Among them:

  • An approximate temperature range (based on some, half-baked “frostbite” concern)
  • Required vaccinations
  • That we’ll be spending much of our time traveling by sled dog
  • Blowtorches will be helpful but not absolutely essential
  • Anyone over 4’1” will be required to wear a pith helmet

Despite all that help, Team TYO has given us absolutely no hints in return (outside of a vague threat from Stephen that Nick and I may end up in a Korean jail). So, given that complete lack of in-kind information-sharing, here’s some guess as to where we might end up.

Tim’s Prescient Party of 5 Predictions

It goes without saying that Team Tokyo has all the tools to succeed. They start in Tokyo (we have to start in San Francisco), all of their trans-Pacific travel is already covered (thanks Greg) and they’re probably in the best part of the world for budget luxury and adventure travel. Based on that, they should really knock our socks off. I’m thinking elephant rides, swimming with blue whales…possibly a summit of Mt Everest?

Carrie doing destination research for Party of 5

Here’s a few general guesses:

  • I think that we will spend at least one night in Tokyo. There’s just too much fun, Instagramable, impressing Greg-type stuff to do there. My hope is that they’ll include either a visit to teamLab Planets, the Studio Ghibli museum, Tokyo DisneySea or some combination. I also hope that they will somehow get Nick to eat sushi.
  • If we go to another destination in Japan, my two guesses are Okinawa or Mt Fuji. Hyatt has some terrific properties in Okinawa (check out this one on Seragaki Island) and summiting Mt Fuji would give them some serious Greg cred. 
  • I think that we will go to either Thailand, Vietnam or both. Both countries are magnificent value destinations, have plenty of terrific food, luxurious properties and great activities. Once there, I wouldn’t be surprised to see them try and gain Greg’s (and our) favor through a jaunt over to Cambodia to see Angkor.
  • I believe that there will be at least one island involved (not counting Honshu, the island that Tokyo is on). This will be either: the Philippines, Bali/Lombok or Okinawa. 
Stephen taking some time to be calm and carry on

So, if pressed for a final itinerary, I’m saying one night in Tokyo at the beginning or end with a stop in the Philippines and a stop in Vietnam with a possible side-trip to Angkor. This would be a jam-packed trip and Stephen famously needs time for relaxation and beauty sleep (See above). But, in the end, I think that Team TYO wants to win very badly and that competitive passion will overcome Stephen’s desire for sleeping. But I do think we’ll all end up needing a nap by the time we get to slink into our suites for the ANA flight back to San Francisco.

Nick’s Numerous Noodlings on Team Tokyo

Predicting where in Asia we might end up seems like a bit of an impossible task. The possibilities from Tokyo are endless, with such an array of places within a 6 or 7 hour flight that I could literally predict away all day and not get this right.

So instead of “predicting”, I’m going to share a couple of routes that I’d love to have planned if I were in Carrie and Stephen’s shoes sandals (if you know Stephen, you know).

One hint we were given is that we were told we would need swimsuits. That could be because we will spend time in a hot spring within Japan, but I’m going to guess that a more tropical beach is involved.

If I were tasked with planning Carrie and Stephen’s portion of the trip, I think what I’d have been very tempted to do would be to use Air Canada Aeroplan to book this itinerary — on flights entirely operated by United Airlines.

For those unfamiliar, that would be Tokyo to Guam, Palau, and Manila. That would be particularly tempting via Aeroplan because it would cost just 25K miles per passenger in economy class or 45K miles per passenger in business class. Add 5,000 miles on top to add a stopover in either Guam or Palau (or Manila before continuing on maybe!).

Making it even more attractive is the fact that (as you can see above) you could fly an itinerary that provides a 21hr stop in Guam — plenty of time to get a room at the Category 3 Hyatt Regency Guam and enjoy club lounge access if you’re a Globalist….or perhaps even book a very large premium suite — and then continue on to Palau, one of the best snorkeling / diving destinations in the world for a stopover before heading the Manila.

Nobody mentioned needing to bring my scuba diving certification, but Carrie did mention that she’s more comfortable swimming in fins, which screams “snorkeling!” to me.

The waters off of Saipan (seen here) were teeming with fish, but the coral in Palau looks to be in much better condition.

Then I believe Manila is a good destination for cheap luxury hotels, and we could easily get back to Tokyo from there for our flight to San Francisco.

I think that might be the trip I’d have done — but I don’t think it’s the trip Carrie and Stephen have planned. Would they really follow Japan Airlines business class (our team flight to Tokyo) with United business class on a 737?

Does it look like Carrie flies a United 737 internationally??

Instead, what I hope they have planned is a trip that includes Thailand. Logical Nick thinks this is highly unlikely because I got stuck in a Bangkok Airport for an entire long layover during 40K to Far Away and I stopped in Bangkok during 3 Cards 3 Continents, so Thailand would seem like a destination that’s been “done” — except it really hasn’t been in the sense that we haven’t featured anywhere else to go in Thailand.

And I know from past discussion that Stephen knows about the InterContinental Khao Yai. Haven’t heard of it? Go ahead, Google it. Here, I’ll save you the trouble — go the hotel’s website. Look at the guest room photos. Tell me the IHG property you’d rather stay at for 30K points per night. I won’t hold my breath. At some point last year, we joked about having a team meeting there — I really hope they’re making that happen!

Of course, I wouldn’t need my swimsuit there. But I would at the Kimpton Kitalay Samui, which also looks pretty darn nice and often seems to be bookable with IHG free night certificates. It would be pretty easy to get both destinations done in a single trip — and Samui also has some great options with Hyatt and Marriott points.

Furthermore, ANA serves Bangkok with a 787 and of course Thai Airways and Japan Airlines all serve Bangkok nonstop from Tokyo.

But do I think Carrie would be satisfied with Thailand as our Asian destination? Not really. Stephen lived in Bangkok for a time I believe. I’ve been to Thailand several times. Greg and Carrie have both been and I assume that Tim has been as well. There are points to be earned for destinations that are new to team members and it would seem relatively difficult to pick up many such points in Thailand (though surely none of us have been to wherever one finds that Intercontinental fashioned like a train and I don’t know whether any of us has been to Koh Samui before). Still, I feel like Thailand isn’t far enough from the beaten path for Carrie to feel as confident as she has at every team meeting for the last two months.

So where do I think we’ll actually go?

My guess is Malaysia. I don’t know who if anyone on the team has been there (some have probably been to Kuala Lumpur, but has anyone on the team gotten farther afield? I don’t know.).

Furthermore, I would definitely need my swimsuit for Langkawi — and either the Ritz-Carlton or the St. Regis Langkawi might have been bookable with either a 40K or 50K Marriott free night certificate (or maybe even a 35K if they found one of these properties at 50K instead of the 52K / 55K rates that are more common).

A couple of nights like that in the lap of luxury and then we would have an endless array of cheap stays at our disposal within Malaysia, with Marriott properties starting under 5,000 points per night in some places.

Will Malaysia be the destination of choice? I don’t know. Would just Malaysia be enough to win? Would it be enough for the devious laughs of confidence we’ve seen from Team Tokyo? It’s awfully rainy in Malaysia right now — as it is in much of Asia. Here’s hoping the sun shines on whatever it is we’re actually doing!

Want to know what actually happens?

If you aren’t yet following us on Instagram, you’ll want to be. Instagram is a better format for sharing short-form video and telling a travel story as it happens, so we’ll be using it heavily throughout the challenge (Follow @Frequent_Miler). We will also post updates to the blog here, but if you want to virtually tag along on the trip and know what’s happening while it’s happening, you’ll want to follow us there. Personally, I think it’s going to be epic. More to come next week. For now, what do you think we’re going to do?

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While I love the concept of the group trip, the scoring system is too arbitrary. I wonder if Greg will suffer from recency bias (scoring more favorably for team SFO for otherwise similar redemption value) or if Carrie and Stephen will set the bar high enough in the beginning that the first impression will be difficult to overcome


While I’d LOVE for you all to come to Guam and join you at HR Guam Regency Club (the Rooming Manager there is just awesome and always takes care of me as a Globalist)… but we just got hit by a MAJOR typhoon and the island is absolutely devastated. Hyatt took a HUGE hit. We’re all in cleanup mode now but there is still no power, running water, internet or cell signal in a lot of places. I’m sitting in the Hilton lobby right now because I can use my hotspot here.
But any how – would love to meet all you guys sometime but maybe skip swinging through Guam right now.
Love your tip though on Aeroplan miles to get from Tokyo to Manilla via GUM and ROR!


Thanks for the tip about InterContinental Khao Yai! That theme is right up my alley. Wow!


I don’t understand why you’d go all the way to Japan to not do Japan. It’s only a 5 day trip! If I was Carrie and Stephen, the entire thing would be in Japan.

Tim Steinke

What would your itinerary be? Stephen and Carrie could use some ideas!


I’m excited to see where y’all end up! Please don’t ride any elephants, it’s now considered animal cruelty.


I agree.

Tim Steinke

Sorry, that was just meant as a joke (like swimming with blue whales and summiting mt everest).


I wasn’t sure since some people don’t know how bad it is for the elephants. Didn’t mean to be negative Nancy and nitpick one thing out of an great article.