Stop the #1 Thing That’s Making You Overpack


Hello friends!

Today’s email contains:

✅ A packing pep talk

🎥 My latest video + your packing Qs

🧳 The surprisingly hot debate around underwear & pajamas

📩 A call for your trickiest packing questions

🌍 A travel tool I’m obsessed with

🌸 Plus: early details on our 2026 group trips!

How I Finally Stopped Overpacking

Packing light is a skill that takes a lot of practice, patience and being real with yourself.

One of the biggest things I’ve always struggled with is that lingering ‘what-if’ voice.

You know the one.

It loves to spin up every possible scenario just to convince you to pack more than you need.

This was the biggest reason I kept overpacking—until I figured out how to shut it down.

When that voice shows up, I try to remind myself of two things:

  1. I always regret bringing too much - more than I regret bringing too little.
  2. If I really need something on my trip, I can probably buy it there.

If you're ready to finally stop overpacking, my latest video shares the strategies that have worked for me—hard-earned through trial, error, and way too many heavy bags.

If anything, I invite you to read through the comments - there's a great conversation happening, and I’d love for you to join in.

Answering Your Trickiest Questions

I’m working on a follow-up video where I tackle your toughest packing questions—things like:

  • What to pack for combo trips (hot and cold weather, multiple activities, etc.)
  • Shoes: how many, which kinds, and how to pack them
  • What to do when you’ve got weight limits
  • And how to handle all the random “just in case” stuff

If there’s a tricky packing scenario you’ve struggled with—no matter how specific—hit reply and let me know.

I’d love to include it.

Pajama Drama?

Apparently the most controversial packing topics right now are underwear and pajamas.

Here’s a quick rundown of how I handle both:

👙 Underwear: gets packed last (number of pairs depends on how much room I have) and then plan to do sink laundry if needed.

🛏️ Pajamas: I bring 2 sets. One to sleep in, the other to wash (usually in the sink) and hang dry.

Group Trip Updates:

Chris and I are planning our first ever group trip in 2026! A big thank you to everyone who voted over on YouTube.

Based on interest, here are the current front-runners:

  • Ireland (I have access to a really fun itinerary for this one)
  • Portugal (I can’t go another year without pastel de nata!!)
  • And very likely Japan (we’re going later this year to scout it out first!)

Stay tuned - more updates to come...maybe we do more than one??

Useful Travel Tool:

If you’re visiting multiple countries in Europe, this tool is a gem:
👉 European Word Translator

Type in any English word like “cheers” or “thank you,” and it shows how to say it in 30+ European languages—on a color-coded map based on language families.

Super helpful for multi-country trips!

This will definitely come in handy for my upcoming trip to Central Europe… so I can properly order a beer in each country 😎 🍻

Intriguing Hotel Deals:

Lisbon: Independente Bica (some dates in June 23% off):

  • This hotel is just down the street from where I stayed
  • Rated 4.7/5 on Google
  • All the best neighborhoods (Chiado, Barrio Alto and Baixa) are within walking distance.

Speaking of Portugal - I have a couple new articles, including this one: 👇

11 Underrated and Beautiful Villages to Add to a Classic Portugal Itinerary

That's all for now,

Aly ✈️

Some of my emails contains affiliate links, meaning if you click through and make a purchase I may make a small commission. I only share information about things I know, love and trust!

Aly Smalls

From capsule wardrobes to luggage that actually fits in the overhead bin, I share smart packing tips, honest gear reviews, and carry-on-only strategies that actually work—because you don’t need 17 outfits for a 5-day trip. Plus: hotel deals, unique travel guides, news & updates, the occasional contest!

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