I arrived at the Toronto airport yesterday with four bags that looked similar to these:

I have an older version of this bag and it is the best travel bag ever!  You can zip off the front backpack and make it its own separate bag or you can leave it attached to the main storage compartment.  The main compartment of my bag had my breast pump with its case (takes up half the space) and shoes and clothes.  It also had papers from my interviews.  The attached front part had all of my toiletries and my tennis shoes.  I intended for this to be my only checked bag.

Andy’s camera bag which had the camera, a detachable flash, a second lens and other miscellaneous camera gear.  I intended to carry this on because I would not trust the camera in the airport baggage system.

My laptop bag had my laptop and two bottle bags full of ten smaller bags of frozen breastmilk.  The bottle bags looked something like this.

I intended to carry on the laptop backpack with milk inside as I would not trust my laptop in a checked bag.

And finally my purse.

My purse was full of toiltries, my book, wallet, passport, water bottle, etc.

All four bags were FULL of their respective belongings.

As I was waiting in line, I overheard one of the representatives from United Airlines say to a gentleman that there was no way he could get past the security checkpoint with more than one carry-on bag plus a personal item.

When she was finished talking with him, I called the woman over to my place in line and asked her if she thought I could get on with a laptop backpack, a camera slingback and my purse as carry ons.  She said no way.  I argued that I needed all three bags and she said they wouldn’t care.

And so you can see my dilemma……

The rules as she explained them as they applied to me were as follows:

- Breastmilk cannot be carried on (as I was intending) unless you have a baby with you

- Only 1 carry-on and 1 personal item (purse)

These rules put a major kink in my luggage plan and I was frantically trying to figure out a new strategy which could be implemented before I reached the front of the line.

Now you know the rules, here are the variables to play with.

- I didn’t want to repack my large bag

- Breastmilk has to be in a checked bag (of which there is no room in)

- Easiest thing to remove from the bag I planned to check was my tennis shoes

- Attached backpack to roller bag could be a separate checked bag

- I took the airplane advice of Holly Burns and packed a Pashmina in my purse

- Camera = very breakable, expensive + it is Andy’s

- Laptop = very breakable, expensive + it is HP’s

- Ideally, I do not want to leave anything, even the breastmilk

- If I do have to leave something, I can toss some papers or free stuff from the NSBE convention currently located in my large carry-on bag

- I am willing to pay for a second checked bag

- I have an empty briefcase type bag in my large checked bag that could be pulled out and used

I think that is enough info.  What would you do if you had been in my shoes?

I will tell you what I decided to do by Wednesday of this week, plus if I am still worked up about it, explain how ridiculous it is to go through the U.S. Checkpoint in a foreign country now.  R.I.D.I.C.U.L.O.U.S!  It is truly amazing anyone bothers to be a tourist in America nowadays.

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