Preparation

The luggage. Not full yet.

Six days until take off. I'm going through everything I think I may want to bring with me.

The first five days are a test of sorts. I have a couple of days with my sister in Chicago and then I'm off to Raleigh, NC for about a day. After that, I'll be back in Boston for 24 hours. During that day I will go through my luggage and figure out what is dead weight and what is missing. The big consideration is whether or not to bring my computer. Let's weigh the pros and the cons:

Pro:

• Speed: I can adjust flights easier and finalize my plans. 
• Connection: Having it with me will make it easier to monitor finances. (This is important as I am looking to travel on the cheap.) Also, since I am working for myself, it would be a useful tool for keeping up with my business.

Con:

• Weight: It's a MacBook, not some little netbook.
• Redundancy: I have an iPhone. It can't do absolutely everything I need.

For the first leg of the trip, I'll bring the computer and see how much it weighs me down.

The next thing to figure out is clothes. I have a hoodie from scottevest. This will be useful for any overworking air conditioning I encounter. I also expect it will serve me well later in the trip when I'll be in the Pacific Northwest. (Cooler in the evening, right?) Of course the big reason for anything from scottevest is the pockets. I can wear this to the security gate with all my crap loaded into the 11 pockets. All I have to do is take the thing off and it through the scanner. Hopefully this will ease some of the anxiety I get, that has me triple checking whether my wallet, phone or keys are still in the little plastic bowl.

As far as the rest goes, I'll bring one pair of pants, a pair of shorts, a bathing suit, 3 pairs of socks, 3 undershorts, 2 t-shirts and a button-down shirt.

Did I mention what I'm packing all of this into? A have a Timbuk2 courier bag. Chock full, this thing is a great carry-on size, but the thing I'm worried about is weight. Over the weekend, I'll do a trial run with this thing packed full. We'll see how it goes.