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.

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.

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.

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.

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!

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.