I still am becoming amazed at the complexity and difficulty in preparing for a trip like the one I am undertaking this fall, but I think I'm going to have it worked out.
The checked bag

Yea, this baby was pricey and so were the packing cubes, but I think it is worth it. I searched for the biggest bag that could be checked without overage fees and this is the one that came up. The limit is 50 lbs and 16 pants and 16 outer shirts plus packing bags puts me right at 48. Cutting it close is still cutting it and this one passed the test.
That leaves me about 27 pounds to play with between the carry-on bag and the backpack.

About 10 pounds of that has to go into the backpack and that's going to include the CPAP, mask and UPS batteries, my neck pillow, cell phones and batteries, eye mask etc...
The trick is going to be getting as close as possible to that 10 pound mark without going over. It's going to be tight but I think I got it worked out.
That gives me 17 pounds to work with on the carry on bag for underwear, socks, t-shirts, power converter, laptop, headset and all the personal care stuff.
My test run has showed me that it's going to be tight, and the bags will all be stuffed but it's going to work out.

In about 2 weeks, I hit T - 6 months and it is so invigorating to be getting all these details worked out in advance.
I leave on a Sunday evening in mid-September and it is my firm goal to be 100% packed and ready by the end of the prior weekend. I want to spend the launch weekend in prayer, contemplation and Adoration to get my myself totally ready for the immensity of this impactful pilgrimage.
Of course, I could simply look at this as a logistical problem to be solved and leave it there, but my mind isn't wired that way. I am always looking for the bigger picture, the deeper meaning.
The person on the outside looking in may look at this and say "give me a break, you are packing for a trip and nothing more".
I could very well agree with them if this was a trip to the Bahamas or an expedition through the Australian outback.
This trip is so much more than that and I simply cannot allow unplanned mishaps or missed details to distract from any part of it.
On my first true day of pilgrimage, I will stand in view of the place where the Angel Gabriel greeted Mary with those words 'Hail, Full of Grace". I will behold the location where some 3 decades later, her Divine Son turned water into wine. In those sacred moments, I want to be overwhelmed with awe and joy with a clear mind. In that moment, I cannot be distracted by wondering if I packed enough socks.

I intend to have the logistics of this trip so pre-planned and fine-tuned that they operate on autopilot while I drown in oceans of Grace seeing the pages of the Bible and the miraculous lives of saints come alive before me.
That is why I am here today, 6 1/2 months out, packing and unpacking suitcases. I want to do the tedious job of figuring out what goes where and how stating today. I could be on as many as 6 flights and easily 4 times that many bus or coach rides. I could be walking up to 75 miles on this trip and I will spend time in perhaps 7 airports and, for sure in at least 8 hotels. If I am not organized and prepared, the logistics of the trip will intrude hugely on the joy of the trip.
That cannot happen. Everything will have its own place, its own bag, its own compartment and I will move like a conveyer belt from place to place, packing, unpacking and marching. I am totally obsessed and meticulous now in order to be as free as possible then.
I get one shot at this. One moment in time. All that I hold dear will be there. The connections will be right before me.
Mary conceived the I AM right here.
Water became wine right here.
In this very place, one boy's lunch fed thousands.
Here is where my Savior was born.
Here is where the cross stood that paid my ransom.
Jesus walked these streets.
The Sun danced in the sky, right there.
This is the birth place of John of the Cross, of Theresa of Avila.
Saint Ignatius wrote the spiritual exercises here.
Bernedette unearthed the miraculous spring over there.
As the trip draws closer, the awe will probably become too big. I imagine a few sleepless nights are ahead. I imagine that I can't even imagine what this is going to be like.
For now, I will make sure I know where my shirts need to go.
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