How We Plan A Trip

How we travel

Planning a long trip takes time — a surprising amount of it — and we have come to think that is part of the pleasure, not a tax on it. This is how the two of us actually go about it. It is a method, not a rulebook; take what is useful and leave the rest.

How we do it — not how you must

How it actually connects

THE SHAPING QUESTIONS — THEY PULL ON EACH OTHER Inspiration Where & who When Cost settles into… THE DOING — MORE ORDERLY Routes Booking Track & pack

Nothing up top settles in isolation — inspiration, where, when and cost keep adjusting one another. Only once they find a balance does the practical work fall into a rough order.

Where, and for how long

The first two questions arrive together and refuse to be separated: where do we want to go, and for how long can we go?

The where is rarely a blank map. It is pulled, first, by people — family and friends scattered across a handful of countries, whom a trip is often built to reach. And it is pulled, second, by a bucket list, though ours is a fluid thing rather than a rigid one: a set of places and sights we lean towards, reordered freely as the years and the mood change.

The how long is the more practical of the pair, and it is really a set of constraints in a trench coat. How much time do we actually have. What budget can we assemble. And — the one people forget — what shape will the trip take, because the shape governs the cost as much as the distance does. Staying with family and making day-forays from their spare room is one kind of trip; moving town to town through motels, hotels and B&Bs is another; sitting still in a hotel for long stretches is a third, and the most expensive of the three. Threaded through all of it is how we mean to move — by car, plane, train, bike, or the combinations that usually win — because the mode quietly decides how far a day can reach.

When to do it

Once the where and the how-long have a rough shape, the calendar has its say. The when is three questions wearing one coat: what is on while we are there, what it will cost at that time of year, and what the weather is likely to be. The three rarely agree. The most beautiful window is often the dearest and the most crowded; the cheapest is sometimes the one nobody sensible would choose. We look for the compromise we can live with rather than a perfect month that doesn't exist — and for anywhere specific, the country guides carry the real seasonal detail.

From a shape to a route

By now there is a general framework — a sense of when, how, where, and who or what we most want to see — and that is enough to start testing itineraries. We sketch routes and hold each one against three things at once: time, likely cost, and plain practicality.

That last test earns its keep. It is not obviously sensible, for instance, to spend thirty-five hours and three changes getting from London to Australia when twenty-three hours and one stop will do it for less money and a great deal less misery. Somewhere between the cheapest fare and the shortest, most civilised journey there is a sweet spot, and much of routing is simply finding it — trip by trip, leg by leg.

The travel-agent test

With a goal in mind and a feel for the cost and the options, we take it to travel agents to see whether they can meet it — broadly on budget and broadly on itinerary. For a big, particular trip they often cannot. What comes back tends to ask us to compromise on the where or the when in ways we would rather not, and we come away with the familiar feeling that we could do it better ourselves, and for less. So, more often than not, we do.

This is not a verdict on travel agents. It is a verdict on complicated trips. For a straightforward week away, the same agents frequently beat anything we could assemble — more on that at the end.

How we book it ourselves

Booking a trip yourself is mostly patience. We spend regular, unglamorous stretches comparing prices, and we have settled on a routine.

For flights we search across several of the aggregators — Momondo, Expedia, Skyscanner and Google Flights among them — to find the shape of the market, and then we always check the airline's own site before booking, because the headline price is not always the one you want to be holding when something changes. For accommodation we start on Booking.com, then check the same room on the hotel's own website; the direct rate is often the same or better, and occasionally comes with something the aggregator won't give you.

None of this is quick, and it is not meant to be. Prices move; watching them for a while is how you learn what a fare is really worth.

Keeping track — the humble spreadsheet

For a long trip we find nothing beats a spreadsheet. It begins as a day-by-day skeleton — where we will be, and how we will get there — and fills out over the weeks with the flesh of it: flight times from here to there, hotel addresses, booking references, the small print you will want at a tired moment in an unfamiliar airport.

We have started using tools like TripIt, which can be very good. But honestly a spreadsheet does much the same job, provided you can reach it on the move — which, these days, you can.

Planning a long ride

A long cycling journey is its own craft, and the planning is a different animal. First we get clear on where we are going and what the route options are. Then two questions that don't trouble other kinds of trip: how to get ourselves to the start, and how to get home from the finish.

In the United States we have always leaned on the Adventure Cycling Association's routes and their route maps, and we have found nothing to beat them. As a stranger in a very large country you want tried-and-tested markers — the topography, and where along the way you will actually find a bed, a grocery, a bike shop, a campsite — and their maps supply exactly that.

In Europe we travel more loosely. We are relaxed about stages, and often ride tactically: the day's destination chosen the night before, and sometimes changed again en route as energy and options dictate. Either way the planning is slow, pleasurable work — routing away from the busy roads, and towards the things worth stopping for.

How far ahead

For a long trip we generally book five or six months out — flights and hotels both — rather than leaving it to the last few weeks. Booked early, the framework holds, and the money behaves.

That leaves the final weeks for a quite different task: gathering the things for the journey, and deciding how they are organised. What do we need close to hand, and what can go into a bag that stays mostly shut? It is a small art of its own, and it is the point at which a trip stops being a plan and starts being a departure.

And when we don't do any of this

All of the above is for the big trips. Six days in Corfu should not demand the same machinery as six weeks in New Zealand, and we don't pretend otherwise. For a short, simple week away we are often perfectly happy to let a travel agent do the arranging — the price is frequently better than we could manage ourselves, and the time we'd spend chasing it is worth more spent elsewhere. The method is a servant, not a master. Match the effort to the trip.

The same questions, somewhere real

Strip the method back and it is really a short list of questions: where, and who for; how long; when; and how we mean to move. Every country guide we write is built to answer exactly those — so the way we plan is also the way to read them. Each destination simply changes the answers, and where the effort is best spent. Start where your trip is already pulling you.

Written from experience rather than theory: this is the way the two of us plan, refined over more than twenty countries and a good many long rides. It is a starting point, not the last word — your trip, and your temperament, will shift the emphasis. That is rather the idea.

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