✈︎ Leaving Syros, Testing New Gear, and Our Messy Journey to Japan

Some trips are messy.

Author

Allie Rockwell
November 25, 2025

Good morning ☀️ from Booked It On Points: A curated collection of travel tips and personal stories by me, Allie→ because you’re meant to experience meaningful travel no matter life’s constraints 👊🏽

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🎒 Two Bags Geo is Testing

Airback Backpack – Okay, I'll admit it. When I first heard about a backpack with a built-in vacuum seal bag, I rolled my eyes. It sounds like one of those "As Seen on TV" gimmicks where you get 30 pounds of stuff into a carry-on by squishing it to death, right? Wrong. This thing actually works. It's a gimmick that actually delivers. If you've ever tried to fit 5 weeks of travel into only carry-ons for a family of four, you'll understand why we're keeping this one.

Aer Travel Pack 3 – There's a reason this brand has a cult following. People are obsessed with Aer's sleek, minimalist aesthetic, and after testing the Travel Pack 3 for four weeks, I finally get it. The organizational pockets are thoughtful without being overwhelming, the laptop compartment is perfectly padded, and it actually looks good, which matters when you're lugging it through airports for hours on end. If you're in the market for a solid travel backpack that doesn't scream "tourist," this is worth every penny.

✈︎ Travel Story

🇬🇷 Our Last Week in Syros and Two Travel Blunders

As many of you know, we move about every 90 days and sadly we are in our final days before we move on from this beautiful place. This is absolutely one of the hardest places for us to leave and here’s why":

First: safety. There is virtually no crime on this tiny Greek island. It's remarkable. Our 8-year-old and 11-year-old can roam the streets, go out to eat, and make their way home all on their own. It's a beautiful thing, the kind of freedom you don't realize kids are missing until you see them experience it.

Second: the mix of locals vs. tourists. It leans heavy on the locals, especially now in the off-season. As a tourist, I don't feel like we're a burden. I'm sure we're eating away at resources and driving prices up, that's what tourism does. But personally, we do our best to avoid contributing to that. To live in a place and feel like you're part of the culture, even temporarily, is always a special experience. And we feel that here.

Our next stop is Japan, but we have a 5-week adventure until we get there. There has been a ton of travel to book, and I’ve made two big mistakes so far. I had to confess these to Geo, which he took with a grain of salt, even though it messed with our budget and our experience. But after talking with other full time travelers, this is just par for the course and I’ve already made peace with it.

Mistake #1: We're only in Bangkok for 36 hours because I got my days mixed up while planning. Classic. Guess we’ll have to check out the city during another trip.

Mistake #2: Our final flight from Vietnam to Japan takes off at 2 AM and crosses a time change. A 3-hour flight that has us landing at 7 AM? I think? It's going to be rough with two kids in tow. Guess we have to toughen them up somehow!

In the end, we get to do this, and we are beyond thankful for that. We'll learn a ton of lessons over the next 5 weeks, and we can't wait to share them with you.

✈️ New routes worth watching: Delta launched seasonal LA to Brisbane (3x weekly through late March), ANA started Tokyo to Milan service, and Turkish Airlines kicked off Istanbul to Santiago flights with a São Paulo stopover according to Aviation Week Network - in case you need a little inspo for that final bucket list trip in 2025.

🙋🏽 This one is for the big feelers in the room. It reminds us that it’s never to late in life to take the trip, to rediscover who you are, to see the world. A new year is fast approaching, what will you do with it?

That’s it for this week. We set off on a Mediterranean cruise next week to start off our travels a bit soft before we jump into all that Asia has to offer! Can not wait to share all the details with you.

Have a great week!

Allie & Geo