INTRODUCTION III: THE PLAN

In which various reservations, intentions, and acts of cartographic optimism are presented for the reader’s inspection

H

aving now discussed why we are doing this and what we are looking for, we arrive at the next obvious question: Where, exactly, are we going?

This is a reasonable thing to ask.

It is also a dangerous thing to answer with too much confidence, because travel plans are fragile creatures. They look healthy enough when viewed from the comfortable safety of one’s own home, surrounded by spreadsheets, browser tabs, and the soothing illusion that transportation companies know what they are doing. But expose them to weather, maintenance schedules, visa rules, airline pricing, local holidays, human error, digestive betrayal, or the mysterious international force known as “because reasons,” and they may immediately start shedding feathers and begin making distressing croaking noises.*

So, with that caveat firmly in place, here is the plan.

Or at least, here is the plan at the moment.  So far.  Kinda.

The Itinerary
We expect to begin in September by leaving Oregon, which seems like a fairly traditional first step in a journey intended to take us away from Oregon.

The first leg should take us by train northward through the Pacific Northwest, because if one has the option of beginning a grand world-circling retirement adventure by boarding a train, one should probably do that. This is especially true if one has spent much of the preceding several months explaining that trains are civilized, airports are punishment, and the whole point of this undertaking is to make questionable decisions in a dignified fashion.

From there, we expect to visit Vancouver, British Columbia briefly before flying to Maui, where we will spend some time with friends and attempt to adjust to the idea that we are no longer merely planning the trip, but have actually left.

After Maui comes a quick hop to Honolulu, and in Honolulu we will board a ship bound for New Zealand.

This is important. Not because it is necessarily the fastest way to reach New Zealand** but because it is considerably more interesting than being folded into an airplane seat for a length of time normally associated with geological processes.

The ship should take us across the Pacific to Auckland. Once in New Zealand, we plan to spend time in Auckland, Rotorua, Wellington, Christchurch, and Dunedin. This portion of the journey is partly scenic, partly social, and partly an attempt to personally determine whether New Zealand is as infuriatingly attractive as everyone keeps suggesting.

After that, Australia. More specifically, Sydney, where we have friends, lodging, and what I assume will be numerous opportunities to discover that Australia is exactly like all of our undoubtedly well-founded*** beliefs about the place lead us to expect.

From Sydney, the current plan is to fly to Bali, where we expect to spend several weeks before boarding another ship, this time from Bali to Singapore, with stops in Malaysia and Thailand along the way. Bali is on the itinerary partly because it is interesting in its own right, partly because it is geographically useful, and partly because when one is already wandering around the planet, “several weeks in Bali” is the sort of phrase that sounds awfully attractive.

After Singapore, we intend to head off to spend a month or month and a half in the Philippines, which matters because it is the first of our “serious retirement possibility” stays, as it has remained stubbornly interesting throughout our research, especially around the Dumaguete / Valencia area. Any place that continues to hover near the top of the spreadsheet despite repeated attempts to compare it with half the planet deserves a proper look.
Then we’ll spend four or five days in Vietnam and then a couple of months in Thailand. Thailand has been one of the major possible retirement destinations from the beginning, so we expect to spend real time there rather than merely rushing through, gawking at temples from the window of a moving vehicle, and declaring ourselves informed.

From there, the plan becomes more oceanic again.  We’ll take trains, where possible, south through Malaysia and back to Singapore.

In March, if all goes according to plan, we board a ship in Singapore bound for Cape Town, then continue onward to Europe. This is an absurdly indirect way to reach Europe, which is one of its chief attractions.

Once in Europe, the exact order remains subject to change, revision, reconsideration, and possibly whim. We expect to spend time in places like Prague, Vienna, Croatia, Greece, Italy, Portugal, Spain, Malta, and other locations that have spent entirely too much time loitering around the retirement spreadsheet looking plausible.

Eventually, after a sufficient number of apartments, trains, ferries, grocery stores, laundromats, minor confusions, and meals of uncertain but memorable composition, we hope to know a great deal more than we do now. Whether that knowledge will prove useful remains to be seen, but either way, it’ll be interesting.

Why Slow Travel
There are people who enjoy visiting twelve countries in fifteen days.

We wish them well… but that is not what we are trying to do.

The goal of The Grand Detour is not to collect passport stamps, sprint through landmarks, or return home with forty-three photographs of places we do not remember having visited. We are not trying to “do” Europe, “do” Southeast Asia, or “do” anything else that makes an entire region sound like an item on a household chore list.
We are trying to evaluate possible futures, and that requires time.

A few days in a place can tell us whether it is interesting. A week can tell us whether it is enjoyable. A month may begin to tell us whether it is livable.

Not definitively, of course. We are not pretending that thirty days makes us locals. It does not. At the end of a month, we will still be visitors, still outsiders, still people who may confidently walk the wrong direction to a grocery store they have already visited twice.

But a month is long enough for some of the novelty to wear off.

It is long enough to buy groceries more than once.

Long enough to do laundry, get a haircut, or even get slightly bored.

Long enough to discover whether the neighborhood is pleasant after dark, whether the bus system makes sense, whether the apartment is comfortable, whether the internet works, whether the food continues to delight, and whether the place still seems charming after one has been mildly inconvenienced by it.

That last bit matters.

Everywhere is charming when nothing has gone wrong.

We want to know what a place feels like after something has gone slightly wrong.

Not catastrophically wrong, ideally. We are not hoping for catastrophe; just ordinary wrong. The kind of wrong that happens in real life: a missed connection, a closed office, a confusing bill, a noisy neighbor, a medical appointment, a bus that never arrives, a washing machine whose user interface appears to have been designed by the Riddler.

A place we might call home needs to survive ordinary wrongness, and slow travel gives us at least some chance of seeing that.

It also makes the trip itself more humane. We are not twenty-two-year-old backpackers sustained by instant noodles, optimism, and plentiful cartilage. We are newly retired people with aches, prescriptions, and a growing appreciation for chairs.

Moving slowly means less packing and unpacking. Fewer travel days. More ordinary days. More chances to settle into a rhythm, find favorite places, and notice the difference between a destination that is merely impressive and one that might actually fit.

Trains and Ships
If there is a theme to our transportation preferences, it is this: We would rather not fly unless flying makes sense.

Sometimes it will. The world is large, oceans remain inconveniently wet, and no amount of personal preference will allow us to take a pleasant commuter train from Sydney to Bali. But where practical, we prefer trains and ships.

This is partly because they are more comfortable. I am not a small man, and modern air travel has not been designed with my personal geometry in mind. Airlines seem to believe human beings are stackable, compressible, and best transported in a posture rather more fetal than comfortable. Trains, by contrast, allow one to sit like a person.

Ships allow one to unpack, sleep in a bed, cross oceans, and occasionally stand on deck contemplating the horizon like a minor character in a novel who is either about to have an adventure or has just made a terrible financial decision. There is also the simple fact that trains and ships make the journey feel like part of the journey.

Airplanes teleport you**** from one place to another with a security line, a cramped seat, and a tiny bag of pretzels as a viciously unpleasant stand-in for The Romance of Travel.  Trains and ships have progression. Landscape. Weather. Time. The sense that one is moving through an interesting world rather than being sealed in a pressurized tube and fired from one blandly depressing airport to another.

Since The Grand Detour is meant to be a long, slow examination of where we might want to live, it seems only fitting to travel in ways that allow us to look out the window and notice things.

Besides, if one is going to make a wildly impractical life decision, one might as well make it scenically.

How Long We Expect to Travel
The honest answer is: long enough to learn something, but not so long that we forget what we were trying to learn.
We expect the first major arc of the journey to take many months, likely well over a year by the time all is said, done, revised, delayed, rescheduled, rebooked, and explained to customer service representatives in several countries.

That does not mean we expect to be in constant motion; quite the opposite, in fact.

The whole point is to avoid constant motion whenever possible. We want long stays. Month-ish stays. Enough time in serious candidate locations to breathe a little, unpack a little, and stop treating every day as though we are obligated to wring Maximum Tourist Value from it.

Some parts of the itinerary are fixed, or at least fixed-ish, because ships and trains have schedules and tend not to reorganize themselves around our personal narrative needs. Other parts are deliberately fuzzy. We want room to adjust. If a place deserves more time, we may give it more time. If a place turns out to be a poor fit, we may move along. If transportation plans collapse, as transportation plans occasionally do, we will mutter darkly, consult the spreadsheet, and develop a new theory of the case.

Eventually, we hope to narrow the field.

Maybe we will find a place that feels right.  If we’re really lucky, we might find several and have to choose among them.

Or maybe we will discover that our assumptions were wrong in some fundamental way and that the entire spreadsheet needs to be taken out back and humanely dispatched.

All of these are allowed outcomes.

This is not a road trip toward a predetermined destination. It is a search.

The plan is to travel slowly, look carefully, live ordinarily where we can, and pay attention to the difference between places that are fun to visit and places where we might actually want to wake up for the next twenty years.

After that?

We settle down.

Probably. Eventually. In theory.

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* And/or pining for the fjords.

** It very much is not.

*** We’ve watched both Crocodile Dundee and Crocodile Dundee 2, so you might say we’re pretty much experts.

**** Slowly.