Howdy, folks! 👋🏻

April here.

The team is offsite this week, so we're doing something different. No breaking news, no card tips; those come back Monday, August 31.

While we’re out of office, you get to enjoy one experiment stretched across four days. It’s a bit of a longer read time, but I think it’s worth it. 😉 

Here's the setup, and I made it deliberately super-duper challenging. After all, I’m working with elite miles and points athletes here. 💪🏻 So let’s see what the Demi Vollering, Katie Ledecky, and Auston Matthews of the travel rewards world can do with a limited budget of miles and points during of the busiest travel weeks of the year…

The Challenge

Working at Daily Drop spoils you. We travel constantly, we work asynchronously, and if award space opens up on a Tuesday, we can move the whole trip to Tuesday. Almost nobody else lives like that. Most of you get a fixed number of days a year, and most of those days are already promised to somebody else: a kid's spring break, a parent's surgery, the wedding you can't skip. What's left over is what you get for yourself… and it’s not much. IYKYK.

So you do what everyone does. You build the trip around the days you already get for free.

Most offices close Thanksgiving Day and the Friday after. That's two days of vacation you don't have to spend. Wrap the weekends around them and seven nights costs you three days of PTO.

That's the week I handed the writers: November 21 to 28, 2026. Real dates, real Thanksgiving award availability, no pretending. When did I give them the assignment? July 27. That’s right. Try and plan a last-minute vacation, 4 months out.

They didn't get a fat points balance either. If you’re new to the game like I am, you probably don’t have many points outside of a welcome offer you earned.

Everybody started on the same line:

•  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

For one person, that's workable. For two, it's comfortable. For four, as they would all tell you… it’s a LOT.

So: in a miniature run of Get Me To… Today we're going to Italy. 🍝

• Mike is going solo.

• Katie is planning for two.

• Sam has a party of four.

Same country, same dates, same starting balance. Three trips that barely resemble each other.

Mike, party of 1: Innsbruck to Lana to Cortina to Venice

Mike went alone, and he went to the mountains. The Dolomites, specifically, which he will tell you is the only part of Italy worth defending. He has opinions about this, because… he’s Mike.

He flew into Amsterdam and slept his first night in Innsbruck, just over the Austrian border, before crossing into Italy the next morning.

Here's his move: he flew Delta without touching a single Delta mile. Seattle to Amsterdam nonstop, priced through Virgin Atlantic Flying Club at 30,000 points. Delta wanted 86,100 SkyMiles for that same seat in basic economy; Virgin put him in a better fare class for roughly a third of the points.

Points: 200,000, spread across four programs
Cash: $692
Cards: 2
The tradeoff: four programs, four hotels, seven nights, and not one point left over

Solo travel means you only ever need one award seat. He used that freedom.

Katie, party of 2: Florence to Tuscany to Rome

Katie planned for two out of Houston, and she broke one of my rules to do it. (This would be a pattern with her; I’m calling her “Rule Breaker Begnoche” from here on out.)

Flying out the Saturday before Thanksgiving was going to run more than 100,000 points for two people, one way. So she moved the departure to Monday instead of Saturday, with a return on the next Monday. Same route, same airline, 37,500 points for two.

Here's her move: flexibility beat every clever routing trick on the board. One day of movement was worth more than all of them put together.

Points: 190,000
Cash: $826
Cards: 2
The tradeoff: One additional PTO day used

Sam, party of 4: Rome to Naples to Rome

Sam took four people to Italy from Boston. She had never booked for four before, and her verdict was that it's a whole other animal. 🐻

Here's her move: transfer bonuses did the heavy lifting. A 30% bonus turned 52,000 points into 40,000 for the flight over. A 70% bonus turned 40,000 points into 24,000 for two nights in Naples. Without those two bonuses, this trip doesn't happen.

Points: 189,000
Cash: $1,874 of her $2,000
Cards: 3
The tradeoff: an apartment instead of a hotel in Rome, Holiday Inns instead of anything fancy, and $126 left when the dust settled

Her flight over cost 40,000 points for four people. Her flight home, same four people, same trip:

110,000 🫣

The weekend after Thanksgiving is a rough time to fly.

The scoreboard

All three landed within 11,000 points of each other. Where they split was the cash.

Tomorrow: same rules, same dates, and we're going to Japan. 🏯

Ciao,

April

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