Adventures Around The World

Once we decided that our primary goal with the trip was to see as much stuff as we could on the other side of the globe, we still had to narrow in where we’d target.

Our main considerations:

Nearly every place should be new to both of us. Again, the point is to see far-flung places that we couldn’t otherwise get to during our normal vacation time.

And our plan was to save most of the “top tier” destinations for later, as those worked well as standalone trips that we could pull off during “normal” 2-3 week vacations in subsequent years. So most of the places that ended up on our itinerary were places we wouldn’t book a specific trip to go see. Our strategy here might seem a bit surprising to many. But our eventual goal is to visit as many countries as we can—hopefully eventually all of them, so being strategic about what we do and what we save is important.

We knew we wanted to “anchor” the trip around a long African tour and safari—which definitely is a top tier destination for us. It’d be the easiest way to travel through, and between, a number of African countries. And, crucially, we wouldn’t have to book each day’s transportation, lodging, and day tours separately, which took a lot of planning stress out of the mix immediately¹.

We also wanted a diversity of experiences, and occasional “Western-ness.” While this adds a lot of complexity in terms of packing (and forces us to check luggage—sigh), we figured that we’d really appreciate regular changes in vibe on such a long trip. And since we haven’t spent such a long period out of the country before, we tried to intersperse more familiar-feeling destinations in between those that’d be more foreign to us.²

We added a “zero day” roughly every week, so we had built-in time to sleep in, do laundry, shop for supplies, and catch up with friends back home³.

We knew that this type of trip would entail a lot of flights. And, unfortunately, we’d need to check luggage for each of them. But we tried to keep the flights as reasonable as possible, limiting duration, layovers, and cost.

In addition, if we had to layover somewhere en route to the next destination, we should take a day or three to explore a bit before moving on.

We prioritized visiting Taiwan, Hong Kong, and Macao first, just in case future political trouble made them hard to visit later.

We originally decided to keep the last 20 days completely open. But after some reflection, we decided that it’d be better to plan something out; we didn’t want the added stress of trying to decide, research, and book things during the other sightseeing days of our trip. We also wanted to be sure to “end on a high note,” so we chose to finish in Australia and French Polynesia (read: Tahiti and Bora Bora). We wanted something near the end that we’d be looking forward to (Australia) and that would also be more relaxing and stress-free than other destinations, figuring that we could easily be getting tired of travel by this point. While Australia is the only exception to the “only new places” rule (Jen visited previously), we could still “leave it open” by renting a campervan, which would provide a lot of flexibility in how we traveled.

General thoughts

This will definitely be our most challenging trip ever.

We’ll be stretching both of our comfort zones in a number of ways. There are a lot of logistics, and a lot can go wrong when you’re traveling for 100 days—canceled flights, lost baggage, theft, illness, and countless other things. And we’ll likely have to pivot and skip something(s) on our itinerary to get back “on track.” I’m sure we’ll make plenty of mistakes along the way.

But it’ll be an adventure, that’s for sure!