How to Pack for Two Weeks in a Carry-On

Confession time? I'm an over-packer. There's no way around that. Mainly because I'm probably overly cautious. I used always to want to prepare for the worst and every eventuality. But years and years of hauling hefty bags across long distances has taught me that bringing way too much stuff just isn't worth the exhaustion and stress. In Japan, you are travelling on the rail a lot, and most cars don't have any room for luggage. If your bag is too big to fit in front of your seat, it might not fit at all. So packing everything you need in a carry-on isn't just helpful, it's sometimes necessary. Many European trains are the same. I will say, that we saw lots of people with significant bags and they were just fine in the major cities but if you plan on travelling to countryside towns, where you might even have to take a bus to reach your destination, the smaller - the better. So here are some great tips to help you pack light without feeling like you're leaving everything behind.

How to Pack for Two Weeks in a Carry-On

#1. Get a GREAT Carry-On Suitcase

I think that if you find a fun suitcase that makes you happy, it will make packing lighter, all the easier to do now that you have such a cute little package to put everything into. Most airlines now charge for checked baggage so by using the carry-on you'll be saving sometimes hundreds of dollars. Money that can be put back into experiences on your trip. Airlines have great information on their websites about sizing, and every airline is different so be sure to check the website to ensure your bag will fit in the overhead compartment. This site has a great at a glance guide to give you a general idea of sizing.

You don't have to opt for a full-on suitcase if you prefer a large knapsack or carrying bag but I love having wheels since it makes it much easier to go long distances with ease. I got this adorable suitcase at a swap meet. Nothing fancy and it has held up after over a dozen trips. You don't always need to spend a lot of money to find something fantastic! Winners, Home Sense and Marshalls always have incredible deals on luggage and often in unique colours and designs.

How to Pack for Two Weeks in a Carry-On

#2. Invest in Packing Cubes

If you can afford it, packing cubes are so helpful in not only organizing your suitcase but in condensing it too. I used to use large ziplock bags which worked similarly well. Fill a bag with one category of clothes and compress. Packing cubes are more reusable and let's face it, look a lot prettier too. I'm currently obsessed with the new collection from Oh Joy + Calpack - I mean who wouldn't want to get packing with these amazing designs?! Unfortunately for me, they don't ship to Canada, but I got mine on Amazon for only $25 for a 7-item set! 

How to Pack for Two Weeks in a Carry-On

#3. Pack In Advance!

My best piece of advice is to pack well in advance. Chances are you probably know what the general weather will be like when you arrive so working with that, put everything you want to bring into one pile. Don't try and edit for the moment, just put it all into a large laundry basket or lay it out in another room. After a week or a few days, come back and reassess. You'll realize upon second look how much stuff you don't need. So much of what we pack is unnecessary and only done because we're rushing and not thinking it through.

Here is the itemized list of what I bring for two weeks away:

How to Pack for Two Weeks in a Carry-On

I chose to bring a raincoat since we were expecting some rain on this trip, but you could just pack two jackets of different weights if you aren't planning for rain. It's always good to pack a light jacket even if the weather will be warm because chances are you'll be out exploring late and after the sun goes down, so does the temperature! I choose three pairs of pants, but you can do a skirt as a bottom instead. Make sure to pick one pretty dress or top which works a for a fancy night out. Don't overestimate how many "fancy" outfits you'll need. Chances are you'll need none, but one is more than enough. Make sure to note which items are the heaviest and make a point to set those aside to wear on the plane. Ensure they'll also be comfortable, you don't want to save on space but end up suffering on that long-haul flight. 

If you're looking for tips on how to stay as comfy as possible on the plane check out this post!

How to Pack for Two Weeks in a Carry-On

#4. What NOT to Bring!

Forget the toiletries! Don't' bring shampoo, conditioner, soap etc. Unless you have a certain medical or skin condition which might require special products, these are unnecessary. If you buy the "travel" versions, you'll end up paying way more for a tiny little bottle than for a huge regular version. Every country I've ever visited has had convenient places as soon as I get to my hotel where I could find these items. Often, it's a fun little adventure exploring grocery stores and international pharmacies. I love discovering new products and use this opportunity to try out something new! If you're staying in a hotel, you'll be able to get free shampoo, conditioner and soap. If you ever run out, just as the front desk and they'll bring you up some new ones right away. 

Pyjamas. I know this sounds crazy but for something you're just going to wear at night, it's not worth space in your bag. Instead, just make sure to wear some leggings on the plane and a comfy t-shirt which can double as PJs. In Japan, a lot of hotels actually provide you pyjamas upon arrival! Which is a huge plus!

 Us in our Ryokan provided PJs

Us in our Ryokan provided PJs

#5. What to Bring?

Choose lightweight, packing friendly clothing. Anything that wrinkles should be thrown back into the closet. Anything that is hard to wash - toss that away too. You want quick dry items in case you decide to wash your clothes in the hotel bathtub (trust me, it works!).

In addition to your suitcase carry-on, you are allowed to have a "personal item". I pack a large bag or knapsack with all my onboard necessities. Inside my suitcase, I pack a small handbag or mini knapsack for when I arrive and don't need the larger one.

How to Pack for Two Weeks in a Carry-On

Although I talk about not bringing many toiletries with you there are a few items which I do bring. One of those items are band-aids and blister cushions. Long days on your feet can take a toll no matter how comfortable your shoes are. And a blister always shows up at the most inconvenient time. Blister band-aids are often hard to find and sometimes very expensive (always marked up for tourists) so I ensure I pack a few in my day bag. The other thing I bring with me from my home country are Tide to-go pens! These aren't available all over the world and they do wonders for helping your outfits last a little bit longer before having to be laundered. And if you're a clutz like me, (I am constantly spilling things on myself) they are a lifesaver. Just remember to put them into your liquids bag when going through security!

How to Pack for Two Weeks in a Carry-On

#6. Plan your Outfits

Once I feel like I have all my items, I make sure to play around and mix and match to see that everything goes together. This also gives me the opportunity to ensure everything is clean. Sometimes if you're travelling somewhere in hot in the middle of the winter, you'll grab a shirt out of storage, only to realize it's got a big stain or just smells musty. Another benefit of packing in advance is you have the chance to remedy these issues without rushing and staying up till 1 am the night before a long flight. While I don't always pack in neutrals, I do try to stick to an outfit colour scheme. For this trip, I chose "springtime pastels". This way, no matter what I grabbed from my bag, it would coordinate nicely with any other item.

How to Pack for Two Weeks in a Carry-On

TIP: Travelling isn't the best time to try out new things. As much as you might want to bring that new dress you've never worn, it's better to stick to tried and true pieces from your wardrobe that exemplify your style and you know look great. I know a lot of other blogs will have very neutral and basic items, but that's just not me. I'm the most comfortable in loud, eccentric pieces but if you love casual, neutral basics then that's even better. You'll find the more neutral and simple the looks, the easier it will be for you to mix and match and make lots of different outfits.

#7. How to Pack It

Make sure that when you're packing, you roll everything up together. This really saves space and makes items easier to find. I often will layer clothes with dryer sheets to keep everything smelling fresh! I also put a few new dryer sheets into my suitcase in a ziplock bag to replace the old ones with as I go and it really works.

I also pack a few extra ziplock bags to use along the way as places to store dirty clothes or even as extra storage for things I might buy along the way.

How to Pack for Two Weeks in a Carry-On

To save space I always pack up my socks, tights and underwear inside my shoes. Roll them up tightly and they fit perfectly in your second pair of shoes. It's a great way to use that otherwise wasted space. Store your earring and small necklaces in these tiny pill cases which I bought from the Dollar store. They are light but ensure that your jewellery doesn't get mixed up in your suitcase. Larger necklaces I wrap in clingfilm to ensure they don't get tangled, sounds a bit odd but trust me; this is a jewellery-saving technique.

How to Pack for Two Weeks in a Carry-On

I'm someone prone to getting sick and also struggle with my auto-immune disease, so I'm always travelling with a lot of medication. I take only what I think I'll need and put it into a set of labelled pill boxes instead of bringing the entire bottles of medication. Saves a ton of space and buying medication when you're in a foreign country just isn't something you want to risk. Make sure your medication is never put into checked luggage (if you decide to gate check for instance) since you don't want to risk it getting lost. This is only for over-the-counter medication, anything that is prescription should be kept in its original bottle with your information on it for inspection. If you're bringing liquids with you, remember that they have to be under 100ml and inside a clear bag for TSA inspection. I always keep this part of my bag easily accessible before going through security and then can pack it deeper down after I'm through.

#8. Plan on Doing Laundry

For a two week trip or longer, laundry is going to be something you'll have to do. You can research places to go in advance or ask your hotel reception for the closest location. Sometimes they'll even have laundry facilities in the hotel! If you're staying at an Airbnb, this is often a big plus! My hosts have always been so nice and provided me instruction on how to use the machines. Even if they can't show you in person, be sure to ask for these instructions in your communications with the host.

How to Pack for Two Weeks in a Carry-On

Now you're set for a great trip without being weighed down (quite literally!). After you do this once, you'll realise how easy it really is to pack light. Getting over that first-time hurdle is the toughest part but with these simple tips, you'll be off to a great start!

How to Pack for Two Weeks in a Carry-On
How to Pack for 2 Weeks in a Carry-On