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Packing it all in: traveling with one bag
Once you've picked out the perfect suitcase -- sturdy, light, and small enough to handle easily -- it's time to fill it. A suitcase is basically a big, empty hole. If you just toss things in, they're going to wander around until it's a complete mess. Your bag needs a little help keeping things organized.
When packing for a trip, most people lay everything nice and neatly folded in the suitcase, tie it all down with the built in straps, then stand the suitcase up — and all of the clothes promptly end up in a heap at the bottom of the bag. This is actually the cause of all those wrinkles in your clothes. A few years back, experts in packing pushed the "bundle" method, where you would lay out all of your clothes, flat on top of each other, and then inter-fold them to form a bundle. That kept them neat, but meant that whenever you wanted something from the bundle, you had to take the whole thing apart, then re-fold it again. It was just more hassle than it was worth.
In step these genius little packing folders, which hold everything in neat, orderly and wrinkle-free bundles. Fold your clothes as you normally would, stack them onto the folder and then close up the flaps to complete the bundle. This forms the core of what goes into the suitcase. Other, smaller items will nest around this core. Folders come in a variety of sizes, including 15", 18" and 20". The 18" folder is perfect for my 20" suitcase (remember that the 20" dimension is the exterior measurement, including wheels). For a 22" suitcase, the 20" folder is better. If you're using a 24" or 25" suitcase, get a couple of the 15" version and lay them in sideways.
Once in the hotel I'm perfectly happy to leave the folder in my suitcase and get things out as needed, but I know many people like to feel a bit more "moved in" when they check into the hotel. With a clothing folder, this easy. Pull the clothing folder out of your suitcase, open the flaps and lay the whole thing in a drawer and, voila!, you're moved in. Packing up again is just as easy.
Basically zippered versions of the clothing folders, these cubes (and half-cubes and quarter-cubes) are perfect for all of the little things that roll around in the suitcase looking for a place to hide. I stack them in groups on top and around the core formed by my clothing folder. I have one for my underwear and socks, another for electrical adapters, spare AA or AAA batteries, and non-camera-related electronics, and a third that I use to hold spare camera batteries, memory cards, a card reader, and other photo-related gear.
OK, I admit that there are going to be major differences here, and not everybody will take to my minimalist approach. My wife's toiletries kit looks vastly different from mine. Being a male, with very short hair (what's left of it), my needs in this department are minimal. Some would say Spartan. That extra 2" of suitcase (the difference between my 20" and the maximum carry-on size of 22") should be plenty to accommodate for a larger toiletries kit and still keep you under the carry-on limit.
I like to be able to hang my kit, since many European hotels have limited or no vanity space (pedestal sinks). This also keeps it out of any water that may splash onto the vanity. There are quite a few toiletries kits that include a built in hanger, as well as other nice features like a removable mirror.
To keep your toiletries kit on the smaller side, everything you take should be travel size. Current TSA requirements for liquids, pastes and gels limit you to containers no larger than 3-oz., all of which must fit into a single, 1-quart clear plastic bag. You can purchase travel sizes of things like shampoo, conditioner, shaving cream, deodorant, etc. at most grocery stores, or you can buy empty bottles and fill them with your favorite brands.
The question is, just how much of anything (shampoo, conditioner, etc) are you going to use in a two week trip? Find out now by measuring out a specific amount, write down the date, and see how long it lasts. This is how I know that a standard 0.85-oz. travel size toothpaste will last one person 15 days if they use the recommended pea-size amount twice a day.
In addition to your main suitcase, you'll want a smaller piece, like a tote bag or day pack, that will rest on top of the main piece. The small piece should slip over the handle or hook on in some way, otherwise it will constantly want to fall off while you're walking. Once you board the plane your main bag is going to go into the overhead. This smaller piece will go under the seat in front of you, so use it for things you want access to during the flight, like reading material, a pen, eye glasses, medications, etc.
I use a briefcase, since I'm always carrying a laptop and other electronic gear, but you might prefer a day pack. This can double as your day bag, which you'll carry with you when you're out sightseeing to hold camera, maps, sunglasses, lip balm, etc. The only drawback to a day pack is that many museums will require you to store this in a locker or a secure luggage area while you're visiting the museum. For this reason I use a smaller guide bag (my man purse), which can be taken into most museums.