Estimated read time: 5 minutes, 21 seconds

Hello!

Last day of curated trips by our writers! I hope you’re enjoying this series while we’re offsite.

Today I told them: Roll the dice, and plan whatever you'd actually book for yourself. 🎲

I assumed this would be the most fun for them of all the trips they’ve put together this week. I learned instead that the thought of actually booking this for yourself was almost more overwhelming than having a set assignment. Who knew? ^{🤷🏻‍♀️}

The rules

Now, they did have the same fixed dates as before. November 21 to 28, 2026. Their budgets and parameters were:

• 200,000 points or miles, any program they want

• $2,000 cash

• Flights and hotels only; meals and activities are on them

• Three cards, maximum; bonus points for pulling it off with one

Katie is planning for two. Mike is going solo. Sam is planning for two. The fact that no one wanted to plan for a party of 4… wasn’t much of a surprise. 🤣

Katie, party of 2: Munich, Salzburg, Vienna, and a glühwein in every one

Katie wanted to be standing in a European Christmas market holding food. That was the entire brief she gave herself, and she has the camera roll to prove it.

Her problem wasn't award space. It was the calendar. Every market opens and closes on its own schedule, sometimes differently within the same city, and getting it wrong means flying to a town where the whole thing packed up three days ago. She calls it Christmas Market Math, and she means it as a real constraint, not a joke.

Then she found the cheapest lever in the hobby. Same route, one day later, 24,000 points instead of 50,000. Her advice: work a half day, fly out that afternoon, bring your boss back a cookie.

She also prices the budget version and the bougie version of Salzburg side by side and lets you choose. Sixteen thousand points at a dated property a 25 minute walk from the markets, or 87,000 at a hotel that's been standing since the 1400s eight minutes away. She's honest that the cheap one is the smarter redemption and the expensive one is the better night.

One card, start to finish.

Points: 103,000, or 174,000 if you go bougie in Salzburg
Cash: $1,653
Cards: 1
The tradeoff: she moved the dates a little. Is anyone really surprised at this point??

Mike, party of 1: Los Angeles to Hong Kong to the mountains of Yunnan

Mike went to China, which will not shock anyone who has read the newsletter this year. He calls China his happy place.

The reason it works is competition, or the lack of it. Every other trip in this series hit the same wall: it's the busiest travel week of the year and everyone with a points balance is chasing the same seats to the same handful of places. Mike went where nobody is bidding against him. Award space across the Pacific was open every day that week, out of three different West Coast cities.

Then the prices get ridiculous. A genuine luxury tower in Kunming for 6,000 points a night. A train to Dali for about $20. A business class train seat for $35. Two nights inside a UNESCO old town for 9,000 points and roughly two dollars.

He's also upfront about the one ugly number: $502 in taxes and fuel surcharges on the long haul. It's the biggest single line item in his whole trip and he puts it right out front instead of burying it in a table.

Points: 127,750
Cash: $778
Cards: 3
The tradeoff: the longest flight of anyone this week, and he ran a day outside the window on each end

Sam, party of 2: Dublin, Cork, Killarney, and a rental car the size of a shoe

Sam went to Ireland, in business class, on one card, on the exact dates I gave her.

She made the assignment harder on purpose. I'd said there were bonus points in a single-card strategy, and she's the kind of person who chased a 105 on high school tests, so she went and did it with one card and one program.

Most of her points went into the flight. She found five business class seats to Dublin available on her dates for two people, and once you find that, the trip more or less decides itself. She'd tell you the seat was worth more to her than the destination.

The rest is her being sensible in ways I appreciate. She waited two days to pick up the rental car, because driving on the opposite side of the road straight off a red eye is how you end up in a ditch. She priced the same hotels on two platforms and switched when one paid better. She got the smallest car available and has no regrets about it.

And she admits the fancy hotel at the end isn't really her taste. She booked it because she had cash left and I told her she had $2,000 to spend.

Points: 192,000
Cash: $1,946
Cards: 1
The tradeoff: she used nearly the whole budget, and she got a lie-flat to Europe out of it

The scoreboard

Now compare this against the version of the challenge where I picked the destination. We sent three writers to Hawaii under these same rules and all three of them spent nearly the entire 200,000 and came home with nothing. Same writers, same week, same budget.

This time Mike finished with 72,250 points and $1,222 still in his pocket.

The variable wasn't skill. It was who chose the destination. Mike didn't out-optimize the other two; he went somewhere that wasn't crowded, and the crowd is what sets the price during Thanksgiving week.

Sam spent nearly all of hers and I don't think she was wrong to. She wasn't paying for Ireland; she was paying for eleven hours of sleep on the way there. That's a defensible way to spend a balance as long as you know that's the purchase you're making.

Two of the three had to leave the window to make their trip work.

That's a wrap on the challenge. Twelve trips, one week of dates, and a lot of feelings about how hard is it to plan for 4 people. Tomorrow will feature all of your feedback about this series, as well as the “winning” trips for each destination, as voted on by you. 🏆

Thanks for coming along.

-April

With contributions by Sam Anthony, Katie Begnoche, and Mike Dodge