Melissa and I have grown very practiced at planning travels together, but this one has been challenging in ways we didn't predict. Obviously the scope of this journey changes things, but in ways that are both easier and harder.
It's been really nice not having to worry about getting all of our "anchor" flights in and out of a region in advance, we can just book a one way ticket to where we want to go and (mostly) figure the rest out later.
Also, because we're going to be gone so long and we're just backpacking in (mostly) warm locations, I'll end up bringing much less clothing for this trip than I did a year ago for just 4 weeks in Tokyo, Thailand and Cambodia. Certainly the bulk of the load from that trip was for different lifestyles in different phases, e.g. office wear for Tokyo, shorts for beaches, and casual street wear for the cities.
Not everything is easier though. Booking one way travel necessitates doing some research into how immigration at our destinations deals with travelers. Jamaica, for example, really prefers to see proof of forward or return travel at immigration, so we had to book our flight to Cancun before we left. Other countries we'll have to see as we go.
Surprisingly though, the biggest difference has been the mental aspect of preparing for this trip. We started talking late last year about the idea to just leave and travel because our lease was up in April and the only thing we knew for sure was that we wanted to go somewhere else. I remember us getting to about 90% ready to quit and travel in January, and some night shortly I said are you ready to do this, 100%, start planning, etc? We both were.
So we spent the first few months doing all of the hard stuff to get ready. I started learning Spanish, we both started getting rid of extraneous possessions (Melissa's favorite activity), stopped buying long lived edibles like liquor and specialty foods (both my favorites) and started drinking & eating down our stores of booze, hot sauces, uncooked rice, spices, frozen chicken bones, etc. We shut down accounts we didn't use and finished getting 100% of our online lives managed by password managers (I strongly recommend this practice for anyone, traveling or not. Getting a catalog of all your personal data exposure online is eye opening, and makes moving a ton easier when you can quickly see a list of all accounts with your real address).
We both filed taxes quite early. We started getting immunizations for travel before notice was in at the jobs. I got my international drivers permit from AAA and adjusted 401(k) contributions months ago.
And eventually, probably late March, we got to a point where all that was left was to wait for the day that we could quit (carefully calculated) and kind of maintain our lives in case the plan to travel didn't work out as expected. We didn't want to book flights before the job situation was squared away and there's only so much you can do without that done, so we fell into a bit of a trap of waiting around for the rest of our lives to start.
I would not recommend falling into this limbo. We've had a huge, massive life change just over the horizon for months, but until the last few days it didn't quite feel real and urgent because we've been sitting on it for so long. There were some spikes of urgency, such as when we quit our jobs and could suddenly start talking about these plans more freely. I had a similar reaction after we choose our first stop (Jamaica) and did my (apparently habitual) manic sprint of research to learn out everything I could about stuff to do and see in Jamaica.
So far this entire last week at Melissa's (extremely generous) parents' house hasn't felt like such a major trip is just around the corner. We've told our story so many times by now, had so many vague conversations about the plan, explained over and over that no, we can't send you our agenda because we don't have one, I really don't know when we'll be back, etc. The trip almost feels old at this point and it's hard to feel a sense of urgency for a long time.
Well, we're now waiting to board at JFK and the last two days have been far more hectic and urgent and it's about as real as it gets. Thanks everyone who's been so supportive to us, helping to get us out of our lives and onto the road!