“How do you pick where you go?” It’s a common question I get, and I understand it. After all, as a travel writer I am fortunate to be able to travel more than most people, and from their perspective I probably always seem to be off on another trip.

So, how do I pick where I go? It’s not really anything complicated or magical, but let me share my process when it comes to picking out a destination.

Flying into London

Where do I want to go?

This is the most basic question, and also sometimes the hardest. I am not paid for my work, so while in some cases destinations will sponsor my trip (mainly here in California), I am not limited in my travels to a place that wants to host me. (Like the positive spin there?) Rather, I pick out places I want to see, from a personal standpoint. After all, if I am happy, that will come across in my writing, and as every place in the world has stories worth telling (remember, it IS possible to like everywhere), I simply get to choose what interests me.

But with my interests spanning nearly every place, whether I’ve been before or not – after all, some of the most amazing trips are seeing a place again but from a different perspective – how do I narrow it down and actually pick?

How much time do I have?

This is the next consideration in my process. I prefer to spend more time in a place than to see more places. So if I have only a couple weeks, I’ll likely pick a single city to visit. If I have months – and yes, I realize few people are able to travel for months, at least not before retiring – I’ll try to see a few, but still at a fairly slow pace.

This leads me to narrow my trip. In some parts of the world, a major city isn’t really close to much else. For instance, I’m going to Cartagena, Colombia in January for two weeks. Not much else is really close, so it’s an easy place to go when I only have two weeks. On the flip side, going to Europe almost always means seeing more than one place and for a longer period, as it is so easy to get around and cities I want to see are closer.

I prefer train stations to airports, all things equal

Cost is a factor.

As much as I wish I were wealthy enough not to worry about costs, I am not, and I do travel on a pretty tight budget. Some destinations are more affordable than others, and I can’t spend six or more months a year traveling and not take this into account. For instance, during my recent month in Buenos Aires, my rented one bedroom apartment cost me around $800 for the whole month. In Barcelona, I spent almost that much per week.

So I have to balance expensive destinations with those that are more affordable. I cannot afford to spend six months a year in Western Europe, or in Australia, or in many parts of the US. Each time I travel to an expensive destination, I have to make sure my budget stretches, thereby necessitating a cheaper trip the next time.

Airfare also adds to the cost, although given my propensity for taking fewer trips that are longer in duration, the differences in costs aren’t as much of a deal breaker. My real consideration is deciding whether to use frequent flyer miles or to pay in cash. That one tends to come down mainly to whether I book a single round trip flight (using cash) or two one way flights in and out of different places (miles tend to work better for these).

Other considerations

There are a few other things I do take into account when deciding between a couple of places.

First, like many people, I track my country count, and all things equal, I prefer to see a new country when possible. So for my upcoming trip to Italy (which I’ve already visited, though not in depth, hence the trip), I’m making sure to include a side trip to San Marino to add another country.

Second, I do prefer not to fly between places if I see multiple locations on a single trip. I try to tie in two or more cities I can visit via train, bus, or ferry. For instance, after Buenos Aires I took a ferry to Montevideo. It is partially a sustainability issue, partially a matter of hating restrictions on what I can bring onto a flight, and partially costs.

Finally, while I love traveling solo or just with A, I do have people I like to see, and arranging places to meet them – or visiting them at their homes – also plays a role.

So that’s how I plan my trips. As I said, it isn’t magical or even all that exciting, but hopefully gives you all a bit of insight.

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