I’ll be documenting each part of our crazy trip coming up, and I thought sharing packing and prepping would be fun.

Packing

So far, we’ve decided on the bags we’re bringing (3 checked).  There’s a good chance that turns into an extra bag, but we’ll see.  We’ve ordered charge adapters, packing cubes, and extra vitamins.  We’ve got a million things to do still. 3.5 months with many, many flights within cold and warm regions requires strategic packing.

I’m sharing a large checked bag with my son, and I’m already at 45 lbs without his stuff… ARGH!

No, I couldn’t take the hot sauce…  I’m still 5 lbs over…

So, we pulled it off!   3 checked bags, and 7-8 carry-ons (depending on snacks/food.) My load will get a little lighter as we give tiny Maui gifts to family/friends along the way, but I know we’ll accumulate new stuff too.  Natalie thinks I’m crazy, but I have a tendency to travel with old clothes I don’t love, with the goal of losing pieces along the way.  It’s a gratifying challenge to lighten the load as I go.  I know it’s weird, but I love it.  This time I like most of the clothes I’m bringing (in order to not be such a freak around my wife.)

2-Day Bag

Everyone’s missed a connection or had a delay overnight.  Since we have 18 flights, we’ve decided to have one carry-on that holds toothbrushes, toothpaste, and clothes for 2 days for each of us 4.  I bought a special bag from Solgaard that has a compression system. Amazingly enough, everything below on the right fits into the right section of the suitcase on the left below.  It wasn’t a cheap bag, but it was worth it.  I used it and their backpack (with the same compression system) for an almost-2-week trip recently to Whistler, Canada, and Austin, Texas.  I didn’t want to check a bag, and I somehow pulled it off.  Winter gear and warm weather gear all made it on the plane (with some side-eye glances at my giant backpack from flight attendants.)

Our Friends, the Scoggins, had the same idea and actually needed it after the first flight of their 28!  They got stuck in South Korea, and were very grateful to have the 2-day bag.  I thought I was being special until they told me that it’s a thing and called a 2-day emergency bag.  This is why traveling with travelers is so key!  Great minds think alike!

UPDATE:  Since our 1st flights had a 10+ hour layover at LAX, we planned to stay overnight at a nearby hotel.  Since it’s a layover with Alaska, we didn’t pick up our bags (something we didn’t plan for.) So, the 2-day bag has already been crucial!  I’m very glad to have broken the trip up a bit.  We’re in Virginia and not all that jet-lagged.

Work

I’m proud of the hustle, delegation, and forethought I’ve had over the last 6 months prepping for this massive trip.  Every time we take a long trip, I get my businesses more streamlined.  It’s an exercise in 80/20.  This last summer we did California, Cabo, and Nicaragua for 1.5 months.  I was able to delegate more, cut out the monthly tasks that don’t return, get rid of a few clients, and systematize my work flow.  Not including work emergencies, I have it set up so that I only have to work for 1 day per month over this summer trip!  We’ll see if that’s realistic…  Fingers crossed!

We’re really excited to meet up with friends and family along the way!  We began planning this trip around 18 years ago here on Maui with our friend’s the Scoggins.  We’re spending some large chunks with them, which we’ve done before (and we all travel well together.) Here are some fun videos from past trips.

Some fun videos with the Scoggin Ohana