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Travel Advice

You've taken care of the "Who," "What" and "When" of your trip; I've written too much about the "Why." Here's how to travel.

When most people travel, they focus first on the “when,” i.e. “When the eff can I leave work and travel?”.  Then, they think about “where”—countries and regions, cities and towns, restaurants and hotels and “what,” whether that entails urban explorations or outdoor excursions. “Who” is obvious (it’s them), but “how” often falls by the wayside. (I think I deal with “why” pretty well on the rest of this site.)

Simply put, the reason travel becomes so difficult for so many prospective travelers is that they fail to consider the practical aspects of their trip until it’s too late. Below, you’ll find a run-down of what I consider to be the most overlooked travel advice topics, which link to writings of mine wherever relevant.

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Emerson famously said that life was a journey, not a destination, but you wouldn’t realize this looking at many people’s travel plans. Tedious as doing so may be, connecting dots is as important as selecting them.

Take time as you plan your trip not only to research the best way to get from point A to point B to point C, but also determining whether it makes more sense to go from C to A to B or any other combination thereof. Often, improper sequencing of a trip can make transportation much more expensive and complicated than it needs to be, i.e. by necessitating air travel instead of ground transport.

It’s for this reason that I’ve written many of my sample itineraries, such as this one for One Month in China, or this one for Two Weeks in Cuba, according to how geography and infrastructure will route you once you’re on the ground.


It’s tempting to assume that fast, affordable internet exists everywhere on the planet. It’s also tempting to assume that you will want or need this when you hit the road. I suggest you assume neither of these things.

A few years ago, for example, I took a deliberately Internet-free trip, which ended up being one of the most rejuvenating experiences of my blogging life. It was also stressful, however, given that I depend on the internet to make my living, which is why I recommend that you invest in a local SIM card (or, in Japan, a mobile WiFi unit), unless of course you have (A) affordable roaming or (B) your company pays your travel phone bill.

Money Matters

Every effective traveler is a “budget” traveler, whether your budget dictates that you should stay in hostels or five-star resorts. There’s nothing cool about paying more money than you need to, even if you earn points on every dollar you spend—especially if you read my recent take down of the entire “Travel Hacking” concept.

Then again, it is important to choose and travel with the best travel credit cards, although I do also recommend traveling with a certain amount of cash—for me, 500 USD for every two weeks of travel works out well. I further recommend that you keep a spare credit/debit card (or two, or three, or four) in hard-to-reach spots, just in case you get robbed.


Time Management

The only thing worse than a do-nothing beach vacation is a do-nothing vacation in a place with countless things to do. I get the idea that travel should be a break from daily life, which is to say a relaxing affair, but trust me: You’re going to be stressed out AF when you return to work and realize you’ve wasted your vacation in a place you may never visit again doing absolutely zilch.

On the other hand, this doesn’t mean packing you schedule full, although I do recommend that you wake up as early as possible and stay up as late as possible, and dine on the go whenever you can to avoid wasting time you could be exploring inside a restaurant—unless, of course, it’s an exemplary one. I’ve found that people who are not good at travel time management can benefit particularly well from my Travel Coaching service.


We are living in a post-material world, but even if you still consider yourself to be a Material Girl, the gadgets you take with you when you travel are as essential to your enjoyment of the trip as anything tangible. This ranges from some of the communications topics I covered earlier, to your camera, to the apps and websites you use to book your trip and assist you as you travel—as much as I hate to admit, Leave Your Daily Hell alone isn’t going to cut it.

Most contentiously, I’d argue that you need to purchase a DSLR camera if you want to take pictures you’ll enjoy looking at by this time next year. I also believe in learning how to take selfies without a selfie stick and reading up on the weird world of travel gear, to name a couple tips.

Long-Term Travel

When I first started this blog, the idea of being on the road permanently seemed bourgeois, if not totally delusional. Today, I get more inquiries from aspiring travel bloggers than I do all the spammy email lists I subscribe to combined. I can’t always respond to these kind folks immediately, which is unfortunate—there’s a great deal of misinformation about location independence out there.

For example, the idea that in order to be location-independent, you need to be a permanent nomad. That lifestyle is not for everyone, yours truly included. Indeed, long-term travel (i.e. trips of about six months for more) is just as valid a life-changing, one-time event as it is a lifestyle choice. Keeping up with the Joneses is never a good strategy, particularly if the Joneses are travel bloggers.