Estimated read time: 5 minutes, 30 seconds

Whew! What a week it’s been! 😅

First of all, I want to thank all of you for your warmth and engagement with this “non-traditional” week of newsletters from the Daily Drop team. We had an amazing planning session in Toronto… and it was the first time in my 25 years of leading people that I have EVER had my staff ask if we can meet for even MORE hours than I’d put in the agenda. 🤯

That’s how die-hard this writing team is. And I feel so blessed to be able to call them my team.

I know what I asked you three to do was really, really hard. WAY harder than you thought it would be. I’d say it was worth it.

Now without further ado… let’s get into the “winning” trips!

🏆 Reader Picks: The Best Trips of the Week

First, one little data-nerd nit-pick: the votes are still coming in for the Wildcard trips we sent you today. But writers have deadlines, and I’m at… mine. So the Wildcard winner is subject to change!

The Winning Italy Trip Goes To… Katie! 🌟

Almost half the votes went to her Party of 2 trip. Mike’s Dolomites (Party of 1) trip finished 16 votes behind, and it was neck and neck every day I refreshed the data to look. Here’s what you said:

• Party of 2 voter: “Two of my favorite places in Italy, no brainer!”

• Party of 1 voter: “I've been to Rome. Done that. Got that t shirt.”

Sam's trip for a party of four came in last, but got the most enthusiastic feedback. One of you did the math and reported back:

• “Sam wins, she got 4 (!) ppl over with fewer miles than anyone else and only $469 per person!”

She moved four humans to Italy for less than anybody else, and you knew it:

The Winning Japan Trip Goes To… Sam! 🏆

People really loved the trip that Sam put together (she won by a wide margin):

• “Looking at Tokyo this Spring and today was incredibly helpful!”

• “Redeeming with Qantas sounds good, plus there's money left over for fun things.”

I do want to say that I wasn’t the only one that liked the Party of 4 trip that Mike told you not to take. Those of you who ARE a party of four liked it a lot:

• “As someone who regularly books trips for a large-ish family on fixed schedules, this looks about as good as it gets to me!”

• “I’m so glad you shared this! I’ve been trying to find the cheapest way to get our big group to Japan.”

• “Traveling with two kids is definitely a challenge. We’ll take any opportunity to get a better deal than outright paying for everything.”

Mike, I don’t wanna be the jerk that says neener-neener, I told you so. (But I just did.) But you put together a solid trip that I would take my own party of four on. ✈️ 

The Winning Hawaii Trip Goes to… Katie! 🥇

Whoa! Party of 4 coming in hot! Our team didn’t forecast a landslide victory for four people – Katie even admitted this was a really tough trip to plan. But you all loved it.

• “Companion passes FTW! I'm taking a very similar trip in October.”

• “We are actually planning this trip in March…spring break time and I’m having a challenge finding flights. We have 100,000 UR points, and a little extra. We are Southwest members and have a bunch of those points as well. Our dates are NOT flexible because of teaching schedule.”

• “I’ve been to Waikiki a few times before but never the other islands. And a party of four is more fun than a party of two.”

   

The Winning Wildcard Trip (so far) Goes To… Katie! 👑

Turns out many of you have always dreamed of going to the European Christmas markets. Some of you even told us that this helped you plan your trip!

• “I have always wanted to go to the Christmas Markets in Europe!”

• “I’m trying to plan to same trip right now!”

• “Europe and experiential travel - a winner. And one card keeps it simple.”

Ireland wasn’t far behind in votes. Heck, by the time this publishes at 6:30 AM tomorrow, the results may have changed.

Also… while Southwest China finished last on votes, it produced some of the best comments of the whole series:

• “I think it really depends on how people perceive American holiday season. I prefer China because I can visit anywhere in the U.S. during the winter if I want to feel like I'm in a Hallmark movie. But you can't recreate China and luxury options in the U.S. for the prices presented in that trip. I'll choose new experiences versus following what's already available.”

• “I like shoulder season and somewhere different. Would do Southeast Asia rather than China though. Been there. I love the adventure of keeping the car slow and traveling more. We are in our 80s and still travel economy. I appreciated your challenge for people who have to travel the standard holidays.”

🤝 We Hope You Feel Seen

About a month ago, many of you wrote to me asking for more practical suggestions for couples and family travel on fixed dates, with limited points and a fixed budget. If we could build them around holidays where people were already off for office closures, even better. (And don’t worry, party of five and party of six people – your itineraries are coming!)

• You asked if we could show more origination airports than East Coast or Chicago.

• You asked if we could show our thought process behind how we’d look for deals and how we’d know what was worth it.

• You asked us to write about the three bucket list destinations of Italy, Japan, and Hawaii specifically.

Personally, I hoped that some of you would feel empowered by this week and go forth and book your own last-minute Thanksgiving trips. And you did!

🏅 April’s Superlatives

You all voted. Now I’m going to give my wholly subjective, “Hell, Yeah” team awards. All of them got an A+ on their homework from this former teacher.

• Most Likely to Break the Rules: Katie (we’ll call her a Rebel With A Cause)

• Take Me Off the Beaten Path: Mike (zigging while everyone else zags)

• Every Detail Covered: Sam (all trips were both adventurous AND thoughtful)

Knowing what card or partner program to use to get you there for the best price and redemption isn’t easy. I wasn’t surprised to see some of these cards come up over and over… but some DID surprise me.

• Most Likely To Get You There Points Program: This one. Pick a card, any card. All of them are solid. It showed up over and over and over in the itineraries.

• Quiet Powerhouse Card: This one. It’s not flashy, and we don’t talk about it a lot, but this card did a lot of work for Mike and Sam.

• Most Unexpected (at least for me): This whole ecosystem. Who knew how powerful it can be? Not me!

As you know, we are able to provide you great content like we did this week because of the affiliate relationships we have with our partners. We’re not just trying to sell you; these are the cards our team uses over and over to book our own travel. If you’ve been sitting on the fence, we say – go for it! Get your passports out and go chase your travel dreams!!

Some of you asked which trips I personally would take out of all of them this week. Basically my answer is: Yes. All of the Above. (Except for those hiking trips. I only want to go hiking if there’s a room full of cheese at the top of the mountain, and I can take a helicopter back down.)

We’re already planning our next whack at this exercise (spoiler alert) since you all loved it so much. In addition, you giving us some grace this week really helped us focus on new ways to bring you great content that helps you travel more, travel better, and save money. 🥰

My inbox is always open if you have more content requests for us! Don’t be shy. 🫣

Have a great weekend, y’all,

April

With contributions by Sam Anthony.