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VIDEO - How to pack for a two-week trip without checking a bag

Now that travel has reopened, the travel bug has hit so many, but with checked bag fees having increased, check out the perfect way to travel without having to check a bag and with the fewest wrinkles possible.

I travel 200+ days each year and have tried just about everything in terms of how to fold clothes, packing toiletries, what to do with laundry, dealing with TSA rules, and what carry on luggage is best. In other words, I’ve finally come up with the perfect way to travel without having to check a bag. This little video will save you time, money, and stress-free travel with no chance of losing a bag, and the hassle of lugging around oversized bags. Enjoy!

One of the most asked questions I get is where are my favorite places to visit. But, beyond that, is the question “do you check a bag?” When I respond with “not it I can help it!” it’s followed up with “how do you pack for a two week trip without packing a bag?”

If you're going to go somewhere for three months, that's different ball game. But if you're going to to go anywhere from three days to two weeks, you simply don’t need to check a bag.

Starting with the suitcase, I’ve tried just about all of them and I really like Tumi carry-ons because they're ultra light when they're empty and they’ve been very durable.


In the video above, I am using the previous model of the Tumi Tegra-Lite line. It’s a 22” hardshell continental carry-on. Here is the latest model:

The bag I now use is the Tumi Arrive Macarthur Expandable Carry-on Packing Case:

I also use the Tumi T-Pass Business Class Leather Brief Pack:

This thing can hold my computer, projector and all the gear. Even the folks at the Tumi store were amazed when I showed them what all it accommodated.

Disclosure: The links above are affiliate links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

Let's walk through how I typically pack a suitcase. In this case, I am going to pack for a trip where I need sweaters because it's a cold location. If I were heading to Bermuda or somewhere where it's really warm, it's easy to pack enough gear without checking a bag.

In this case, I'm going to be wearing some dress clothes as well as some casual clothes. Based on this scenario, here are some tips for you and how to properly pack a suitcase so that you don't have to pay to check your luggage. And you won't get frustrated with lugging luggage in and out of trains, buses, taxis or rental car shuttles.

When it comes to toiletries, I'm not a big fan of those big toiletry bags. As a matter of fact, I love the little Tumi Electronic Cord Travel Pouches. Check out my blog “My favorite toiletry kits.”

I also like packing toiletries, socks, underwear in the channels left from the suitcase handles heading down inside the suitcase. Look for the “Channel packing” blog. By using these channels for smaller items, it leaves me a nice flat surface for packing clothes.

Many people suggest you should roll up your clothes. I respectfully disagree.Take a piece of printer paper, roll it up, then smash it flat. Then unroll it. You’ll find a dozen creases!

Instead, fold them as you see them in a retail store. Lay them flat, upside down, and fold in each side three or four inches, fold the arms down over the folds (see photos below), and then fold them once from the bottom to the top, and then flip them over. You will end up will fewer creases and will be able to pack more items this way.

When it comes to folding a shirt, whether it's a blouse or mans shirt, fold them the same way. Head to any clothing store and look at how the clothes are folded. That’s for a reason!

For this trip I’ll also bring a couple casual shirts, folded the same way. So far, I’ve packed five sweaters, two dress shirts, and two casual shirts and I still have plenty of room in the first half of the suitcase.

For slacks, jeans and casual pants, I hold them by the cuff ends, upside down, put the side seams (inside seam and outside seam together - see the photo), then fold them once in half. This keeps the front press seams where you want them.

Because I’m 6’ 1” tall, I have to add a second fold of a few inches when I place them in the suitcase (see photo). In this case, I’m bringing two pairs of dress pants and a pair of jeans (and I’ll be wearing a pair as well).

If you wear undershirts, or t-shirts, these are easy to pack. I tend to fold them the same way as all the shirts, and then create a layer of them just above the channels. They can be compressed more since no one will see any lines or creases.

For this trip, I’m packing seven of them! This now fills half the suitcase, with another half still available. If your sweaters and clothing take up more than half of your suitcase, it’s quite alright to pack a few layers in the other side of your bag.

Then I put my shoes in shoe bags, but I put socks and a dress belt inside the shoes. Why waste space? Sometimes I can fit a belt (rolled up of course), and one pair of socks in one shoe and two pairs in the other shoe. Then the other four pairs I fit around the edges of the suitcase where the folded clothes are.

I typically will wear a pair of casual shoes, and then bring dress shoes - for a total of two pairs. Nothing takes up more room than shoes! Unless you wear sandals most of the time.

I add the shoes (facing each other) in the second half, and that leaves room for your toiletry bag

Then I add a laundry bag (a small pillow case works - see the blog “Dealing with Dirty Clothes.”

Now you’ve got room next to the shoes for a toiletry kit, a hair dryer (for those, unlike me who actually need one), and even a curling iron, or a couple other items of clothing.

The suitcase now has room for a full week’s worth of clothing and toiletries, without repeating the same shirt or sweater twice. But I said “packing for a two-week trip,” so how do you get to that?

I bring seven days worth of clothes and somewhere around the seventh day, I will actually do a laundry run. When I’ve spent time in Italy, Greece, and other foreign places, we will actually go find a little laundromat. You can just have your hotel do it, and many hotels actually have pay washers and dryers. When traveling to foreign countries, we find it actually fun to find a local laundry. You get in touch with locals, actually see what it's like, how they do the laundry, what the laundromats are like and, by the way they're not always called laundromats.

It takes a couple of hours, but easily beats lugging around and paying to check oversized bags, and it actually leaves you enough room to purchase a few things when you travel.

Then you’ll also have a backpack and that’s where you bring a camera, computer, tablet, maps, guidebooks, and other travel gear. For my business travels, I use the Tumi T-Pass Business Class Leather Brief Pack. This thing can hold my computer, projector and all the gear. Even the folks at the Tumi store were amazed when I showed them what all it accommodated.

By using this simple guide you will:

  • Save the aggravation of paying to check your bags

  • Reduce the chance of hurting your shoulders, legs and feet as you lug around more than 50 pounds in an oversized bag or a second bag

  • Have very little, if any, ironing to do

  • Not run out of hangars in the lodging facilities closet

  • Save the 10 or 15 additional minutes it takes to check your bags before going through security

  • Save money tipping baggage porters and shuttle drivers

  • Never risk the challenge of a lost bag

  • Save yourself half an hour at each end of your trip by not having to wait in baggage claim to retrieve your bags

Travel is supposed to be fun, so the fewer hassles you have, the more time you’ll have to enjoy a truly memorable trip!

Happy travels!


Disclosure: Some of the links above are affiliate links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

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