Party of 5 Predictions – What do we think Team SFO has planned?


Believe it or not, we’re a week away from departing on our 2023 Frequent Miler Annual Challenge: “Party of 5”. Don’t worry – if you’re foggy on the challenge details, let me give a quick recap of the Party of 5 challenge concept…

In short, 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 we’re all five traveling together for two weeks. But to keep that fun element of competition, we’ve divided into two teams. Stephen and I (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. Like any other family, 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, 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.

Again, each team has no idea where the other team will be taking us. We only know which airport they’ll be starting from… and Tim and Nick did throw us one packing hint, forewarning us to be prepared for temperatures between 30 degrees and 80 degrees, (commenting that most of our time spent would be right in the middle of that range.)

Stephen’s predictions for Team SFO’s itinerary

In preparation for putting this post together, Stephen shared some of his guesses, which I’ll include here:

I think Puerto Rico could be on the cards because of Tim randomly asking if you’ve ever seen Hamilton. The traveling show is in PR during their portion of our travel dates.

Stephen & Shae excited to see Hamilton in NYC
Stephen & Shae excited to see Hamilton in NYC – will he be seeing it in Puerto Rico too?

As for where else we’d be going, that’s hard to know. On the one hand I feel like they might try to showcase some kind of great value Hyatt, but they might also specifically try to stay away from that and try to find value in other programs. If they did try to find value with Hyatt, it looks like the Hyatt Centric Montevideo in Uruguay can be great value with points as it’s only category 2 and the cash price is ~$250+.

Another option is Argentina because Mendoza has a category 3 Park Hyatt. Mendoza is wine country, so Tim might have some kind of connections or expertise with which wineries to visit there.

Park Hyatt Mendoza (image courtesy of Hyatt)
Park Hyatt Mendoza (image courtesy of Hyatt)

The fact that they’ve mentioned where we’re going could be cold makes me think we’ll be heading fairly far south in South America. I wouldn’t put it past them to have us visit the southernmost tip of the continent. Having said that, it looks like Mendoza will be in the temperature range they’d mentioned, so perhaps that’s it.

I’ve also wondered if they’re planning a trip to Easter Island as something like that would surely earn them bonus points.

Otherwise, perhaps Machu Picchu as a way to show how that could be done using points.

Alternatively, perhaps a trip to the Falkland Islands and/or South Georgia & the South Sandwich Islands. They’re British Overseas Territories, so maybe they’d be doing that for my benefit, what with me being British and all.

All that said, I wouldn’t be surprised if they’ve tried being sneaky and tried to throw in a few random hints to throw us off the scent and we end up going to places completely different to what I’ve guessed above!

Stephen edit: After reading Carrie’s predictions below, I realized that I’d forgotten Greg had written a post a couple of years ago listing his most anticipated award stays. Number one on that list is Punta Islita in Costa Rica which can be booked through Marriott Bonvoy.

  • Visiting Punta Islita as an award stay – 50,000 points
  • Activities including art/cooking/monkey safaris and more – Free
  • Booking your boss’s most desired award stay for the challenge – Priceless

My predictions for Team SFO’s itinerary

Stephen’s guesses sound like good ones to me, but my predictions are heavily influenced by Drew’s reaction to finding out our ending destination. See, somewhere along the way, we decided that Team SFO would be sharing their ending destination with our spouses, just in case our spouses would like to join us there at the end of the trip. Almost all of my pontifications come from analyzing Drew’s reaction that what they had planned would be “epic”.

Puerto Rico could certainly be “epic”, but Drew and I have already spent quite a bit of time there, so I don’t think that would elicit as emphatic a reaction as he had.

Similarly, while Easter Island would certainly be epic, that’s also a place Drew and I have already seen, so I don’t imagine he’d react so emphatically about that destination either.

Drew and Carrie in Easter Island in 2012
While it’s certainly epic, Drew and I have already been to Easter Island

Stephen’s guess about Machu Picchu seems a bit more likely to me for a number of reasons even though that’s also a place I’ve already been. For one, when Drew and I visited, we took the extremely backpacker approach. Not only are there more luxurious ways to experience Machu Picchu which I think Drew might describe as epic, but Greg has mentioned Machu Picchu quite a few times as a bucket list destination for him. For example he’s mentioned the Tambo del Inka, a Luxury Collection Resort & Spa, Sacred Valley, Peru, which has a private train station to Machu Picchu. Since Greg serves as the primary judge for this challenge, it would make sense to pick a destination that’s been on his bucket list for years.

Best Points-bookable Hotels
the Tambo del Inka, a Luxury Collection Resort & Spa, Sacred Valley, Peru

There are really only three other guesses that keep coming up in my mind. The first is Patagonia. We’ve never been there and I believe I’ve heard Drew talk about it as an appealing destination, so I think it’s believable he’d describe it as “epic.” Not to mention it would likely be in that cooler temperature range described by Nick and Tim in their packing disclaimer.

The second guess I keep thinking of is some kind of Alaskan cruise, for instance perhaps in the Kenai Fjords. Since Nick is basically the Cruise King, I find it totally believable that he’d be able to come up with a points and miles strategy for such a thing, and we all know how much Greg loves fjords, so it would fit really nicely into a strategy geared towards impressing Greg.

Lastly, since we know Nick loves pushing the envelopes of these challenge constraints, I could see team SFO taking what’s supposed to be a sort of North and South America themed launch-point and getting loose with that interpretation to include Hawaii as part of America. Though since Greg’s just been there and the flight time would eat up so much of the allotted time, it would be an interesting choice.

What do you think?

We’ll find out soon enough I guess! In the meantime, I’ll keep puzzling over whether or not I should pack a pair of snow boots, but you should share your own guesses in the comments below!

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On the podcast, in regards to challenges, it is somewhat regularly mentioned how South America is always left out so it seems all but certain they will head there.

Given the amount of award space in lie-flat biz from IAH-SCL and the allure of a cat3 Park Hyatt in Mendoza, it seems an obvious favorite. Mendoza is well known for it’s wine and Aconcagua, the tallest peak outside of Asia make attractive activities.

On most days coming up IAH-SCL has 9 seats available but on 6/8 there are only 2 seats left. Makes you wonder???


We will be off to Chicago next thursday-June 1 at 6 am from SFO Terminal 2 if your around????

Stephen Pepper

Our flight out of SFO isn’t until the afternoon I’m afraid


Maybe dee is flying Spirit and they’ll be in the terminal for a couple of days?


I’ll be in Tambo del Inka in July. I’ve heard awesome things about it. Plus it’s one of the few Marriott properties still worth burning points on. Until Mr & Mrs Smith is added to Hyatt, this is the best points redemption for a hotel near Machu Picchu


“getting loose with that interpretation to include Hawaii as part of America” – I imagine you mean geographically not part of the Americas, but without the “s” the sentence reads a bit like you work for Hertz 🙂

Last edited 1 day ago by MFK

I love that you’re doing a competition based on a family of 5. We often travel as a family of 7, and it’s definitely a challenge to find flight award space for that many and hotel rooms to fit an odd number of people (all teens or adults now). Not to mention finding activities that appeal to different personalities. Looking forward to reading about it!


This competition is just not as captivating as previous ones. It’s just more confusing and more niche (what % of readers really care about the ability to use points while traveling with 5?) than previous challenges. This is the danger of listening to the loudest handful of voices on your blog or SM. Hope you all have fun though.


Cope harder now that you can’t just copy paste whatever experience everyone else is doing these days and realize they’re challenging themselves yet having fun doing it. Must suck to be a sheep like you


Swing and a miss.


People with families struggle to use their points well and go far with them. This is awesome. Too bad that you can’t see past your own circumstances.


I tend to agree – but its still fun. I think the problem is that last years was just awesome and hard to replicate. I watched the draft with the intensity of the NFL draft. I mocked out what i would do. I INVESTED in it. There was lots of build up and excitement. This one doesnt have that (at least not yet). Either way, im excited to see what the team does – and hopefully get a few ideas for the future. Still WAAAAY better than no challnge!


Hamilton? Maybe St Croix/USVI??


The Hamilton and Hyatt bread crumbs had me thinking park Hyatt st kits with a boat ride to Nevis

liam carroll

Fernando do Noronha in Brazil, using GOL via emirates?


Great guesses so far, but I’ll throw my guess into the ring too.

Since Nick loved seeing Santa in the North Pole, I think he will try to find something as close to the South Pole as possible.

Good luck team TYO and SFO 🙂