Estimated read time: 4 minutes, 57 seconds

Aloha, my friends!

We’re in day three of the offsite, and the experiment continues.

Yesterday, three writers took one week, 200,000 points, and $2,000 to Japan and came back with very different impressions of their iteneraries.

Today, they “go” to Hawaii. 🌴

Hawaii is on my bucket list, and odds are great it’s on yours too (at least, according to our Welcome Survey). Volcanos, waterfalls, beautiful beaches, and great food. Let’s see how they put the trips together!

A Quick Refresher

I gave the writing team an impossible travel window and a tight budget: November 21 to 28, 2026. Thanksgiving week?? Four months out?? Am I crazy?

Everybody had the same rules (including Katie, AHEM):

• 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

Here's what makes Hawaii harder than Italy. Italy is a long flight to a place where a nice hotel is reasonable. Hawaii is a long flight to a place where it is not, during the one week every office in America has off.

• Sam is going solo.

• Mike is planning for two.

• Katie has a group of four.

Here’s where they went:

Sam, party of 1: New York to Oahu to the Big Island

Sam flew out of New York (JFK) and split her week between Waikiki and the volcano, because she is not, in her words, a “beach person.” Put her in a forest (or on a bike) and she's happy.

Here's her move: she went against her own values and paid for the good seat. Sam treats flights as transportation; she'd rather spend points on hotel nights than on a lie-flat she'll sleep through. Then she looked at 11 hours in economy, booked business class at 2.56 cents per point, and told us exactly why she caved.

And then she showed us the bill.

The flight home was 75,000 points in economy, and she names it for what it is: not a good redemption, and the best one available. Move the trip two days and that single leg gets more than 50,000 points cheaper.

Points: 200,000 – every single one
Cash: $1,816
Cards: 2
The tradeoff: the splurge going out, a bad redemption coming home, and a zero balance

Mike, party of 2: Seattle to Waikiki, and nowhere else

Mike will tell you Hawaii isn't where he'd choose to go. So he built the trip for people who love it instead of for himself: nonstop both ways, no island hopping, one walkable neighborhood, seven nights.

Here's his move: one card, start to finish. It covered the flights, the hotel points, and the status that made the expensive half of the trip worth paying for.

The splurge is three nights in a five-star on the beach at $510 a night, which swallowed $1,969 of his $2,000 and came back with daily breakfast for two, a $100 property credit, an upgrade, and early check-in.

Then he got to the end of the itinerary and realized live, in the draft, that he'd forgotten to book the last night. So he walks back down the beach to the first hotel for one more night on points.

That made me laugh because it 100% sounds like something I would do. 😊

Points: 195,000
Cash: $1,998 of his $2,000
Cards: 1
The tradeoff: economy seats, and $2 to spare

Katie, party of 4: Maui, and the slow road to Hana

Katie moved her departure to Monday.

Again.

She’s out of control, I know.

It was her whole play in Italy, as well as Japan, and it's her whole play here. I'm going to stop calling it a coincidence. 😑

Here's her move: two adults in her party already hold Southwest Companion Passes, so two of the four seats cost taxes. Four people to Maui (OGG, Kahului) during Thanksgiving week for 90,000 points and $44.80.

The rest is discipline. She paid cash for the first night by the airport because the points rate was overpriced, she ain’t scared to say so. Two nights in Hana so the drive is a day of waterfalls instead of a 12-hour endurance event. Four nights at the resort everybody's parents recommend, on points.

Points: 195,000
Cash: $1,717
Cards: 2
The tradeoff: driving back out the way she came in, because the back side of the island voids most rental insurance

The Hawaii Scoreboard

Look at the first column and the third column together.

All three trips cost essentially the same: 195,000 to 200,000 points. One of them moved one person. One moved four.

Hawaii doesn't care how many people you bring. It costs what it costs; what changes is how many people you split it across. The solo traveler paid four times as much per head as the party of four, and she did nothing wrong.

Also? Nobody came home with points. Three experienced writers spent nearly a full 200,000-point balance on seven nights and a coach seat. That's not a flex, it's a warning label. Shift any of these trips a week in either direction and it costs roughly half.

Flexibility is the most valuable currency in this hobby, and it isn't points.

Tomorrow: same rules, same dates, and it’s DEALER’s CHOICE! All writers were let off the leash to plan any vacation they wanted, for any party size, with the same rules in place (unless you’re Katie, who says, “Rules? What rules?”).

Aloha,

April

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