Travel 101: Every Journey Begins with a Single Step

But a Bit of Planning Never Hurts

I’ve been asked many times how I went about planning my long trip last year, and circumstances finally brought me around to thinking more about the question, and my answer to it. How do you go about planning a trip, whether a day, a long weekend, a couple of weeks or several months? Where do you start? Answer: the basics. Essentially, the 5Ws and H, slightly altered for my own personal preferences, and a few additional considerations thrown into the mix. To make matters interesting, they all interconnect and influence each other.

The 5Ws and H

Who is going?

Most people usually have a general idea on the topic of “who?” Are you going solo? With a significant other? A friend? Several friends? Is this a family vacation?

Who is going matters tremendously, for a few obvious reasons. Flexibility, complexity, costs, and so much more factor in. The more people going, the less likely you’ll want to move often – traveling around Europe with ten friends over a month usually borders on insanity (the phrase “herding kittens” comes to mind). Traveling by yourself or with one other person? Definitely possible. It may be easier to find budget accommodation for one or two in a hostel or couchsurfing, but on the other hand, splitting costs amongst a larger group can work too, as a larger apartment or house on AirBnB – but they likely look very different.

What is the purpose?

Are you looking to relax on a beach? Explore as much as possible? See cultural sights? Have an adrenaline-fueled trip? A combination of different things? You don’t necessarily need to have a specific destination in mind. Just knowing what you hope to get out of it answers this question, and helps narrow possible destinations.

Where – Any destinations in mind?

Is there a destination in mind? Often people know where they want to go or what’s on the bucket list, but get lost from there. I just spoke with a young woman heading to Chile for a semester abroad – but wasn’t sure all what else she wanted to do, whether in Santiago or outside of it. This is fairly typical – you may know where you want to go but need a bit of organization and research beyond that. That’s great – that’s where the other questions come in. Others know the atmosphere they want (this speaks to the purpose and interests) but no idea what places might fit the profile, so “where” isn’t always a given. And that’s great too – it opens up chances to include places they might not have considered if they’d honed in on one place right away.


  Bucket List: Hike the Inca Trail to Machu Picchu  Bucket List: Hike the Inca Trail to Machu Picchu



Is there a particular time of year, due to career, family obligations, or other considerations, that you can travel, or are planning to? Is there a preferred season to travel in? I’ve heard a few people say they are looking forward to a trip to New Zealand in July – and think they’ll be hitting the beaches. Not likely, given its winter in New Zealand in July – an average high of a balmy 57 F.

How long?

Trips can vary from a day to years… how long do you have? Where you go will depend to a great degree on this – unless you want to spend 2 full days of your 7 day vacation traveling.  There’s a reason many Americans don’t go to Sydney for a long weekend, but if you’re in New York, London is do-able. And if you have a lot more time, then there are questions of staying in one place or traveling to several destinations. How long ties into budget as well – typically, the longer you’re gone, the more expensive it gets, though for some countries (looking at you, Thailand), this is minimal, and well worth the extra days if time allows.

  Elephant Sanctuary in Chiang Mai, Thailand  Elephant Sanctuary in Chiang Mai, Thailand

What are the interests?

A friend who is a teacher loves museums; another won’t leave a beach if there is margarita service. One does backcountry backpacking and camping. My mother is interested in wildlife – wolf and raptor sanctuaries are on her list. Building a trip around the things you like to do and what you hope to get out of it is essential. What can be included may depend on season, how long you’re going for, who is going with, etc., but it’s important to factor this in up front.

Other Considerations


There is so much to stay on this, multiple posts will be dedicated to it. It overwhelms a lot of people, and the question of finances makes even reasonable ideas seem financially impossible. My advice? Start with the big ones: long distance transportation, local transportation, accommodation, meals, activities. Nail down a rough estimate on each of those, and you’ll have an idea on the overall cost.


  Train Platform in Selcuk, Turkey  Train Platform in Selcuk, Turkey

There are so many tips, hints, and resources out there to stay safe while traveling that there are literally books out there. The first rule of thumb is: be realistic and put things in perspective. In other words, do not cross anything off on your wish list because CNN ran a story on some danger there six months ago, or your mom’s best friend’s cousin had an issue there ten years ago. Vet your fears – fact check them. Having said that, if you are deeply uncomfortable, you likely won’t enjoy yourself. You may also want to consider other options. I wasn’t too concerned with something happening to me in Egypt, but I knew that something could happen, and having someone who knew the terrain and the language would be of comfort. Solution? I didn’t give up on Egypt – but I did go with a small tour group with an itinerary that covered the sites I wanted to visit. So educate yourself and know your limits, and don’t let unfounded fears keep you from going someplace that you are drawn to. Another category with lots more to come!

Likelihood of Disruption

I’m adding this in due to a recent story from a friend who went to Paris, and was frustrated that a strike limited transportation options. There are a few disruptions that come to mind immediately:

Weather: Know what season you’re going in – winter in the northern, and sometimes southern, US brings blizzards; monsoon, hurricane, and typhoon seasons may factor in. And Egypt was great in early June, but by mid-July, those temps are searing.


  Even rainy season can be fun! ATVs in Siem Reap, Cambodia  Even rainy season can be fun! ATVs in Siem Reap, Cambodia


Politics and Elections: While these may be unpredictable, a quick Google search as to when the next election is may save you a headache. And don’t let this necessarily change your mind – but you will be better prepared. The unpredictable does of course happen: I landed in Greece the day the banks closed, and managed around it just fine, despite many concerned calls and messages that I was stranded on a Greek island. (I can think of far worse situations!) There are reports of tourist cancellations in Thailand at the moment, due to the long-reigning king’s death, and the ensuing uncertainty. If you’re experienced and comfortable with the country and climate, there is often opportunity, as costs decrease as demand declines. But if it’s a concern, you may be able to avoid the more predictable disruptions.

  The Pyramids, Egypt, in June  The Pyramids, Egypt, in June

Strikes: In many European countries, among others, though I’ve experienced this personally and often enough in Europe, there are often one or multi-day local or nation-wide strikes. Baggage handlers may go on strike, crippling airports. The metro workers, or trains, or any number of infrastructure unions, often go through periodic strikes. Other situations arise causing local disruptions. Petra – most of the town – was on strike for a few days leading up to my visit, due to citizens protesting a local scandal. Remember: This is a different culture and way of doing things. You are a visitor. There are typically ways of coping relatively easily, especially if you’re traveling solo or with one other or a small group. But know where you’re going, and if there is a pattern of strikes, be prepared. I’d also recommend keeping an eye on the local news in the month leading up to your visit – not only will this help you become more familiar with where you are going, it will also shed light on any potential trouble that could be predicted. I was receiving messages about a possible train strike in the UK for weeks ahead because I had booked a ticket and was on the mailing list. This allowed me to stay ahead of it and consider other options.

What Concerns You Most?

A standard conversation: “I wish I could do that, but it would never happen.” Me: “Why not?” Other: “Because…”

The typical answer is either money or time off, or both. Once you work through those two, then what’s keeping you from traveling? Go down the list and check yourself. Many times the reasons we give ourselves for not traveling aren’t really “real.” The logistics can almost always be dealt with. The real issue is usually a deeper response of fear; do we really want to do this? There is the excitement of someplace new, combined with the dread of someplace new. Those who dread it will never enjoy travel; those who find it exciting, will, and where a person is on the spectrum rarely moves more than incrementally, unless they have a life-altering experience.

  Didn't believe me? Dairy Queen options in Bangkok  Didn’t believe me? Dairy Queen options in Bangkok

Sometimes discomfort may be offset by getting familiar with a location. One friend almost always eats at chain restaurants alone. It became a running joke that I would send him photos of Wendy’s or Pizza Hut or TGI Fridays from far-flung countries, saying “Look, you can come here!”  I sent my parents a photo of a Dairy Queen and a donut shop in the Bangkok Airport. I avoid chains, but for those are anxious over the idea of a menu they can’t read and food they can’t identify, something as simple as knowing what’s available can help. TripAdvisor is also great for getting a good idea for top restaurants, and checking out reviews and menus in advance.

For Americans, luck is on your side if you have a fear of operating in another language. Of course this can be offset with visiting Australia, New Zealand, Ireland, the UK (though good luck with the Welsh – I’ve never been able to understand the dialect!), or any of the many other countries where English is heavily used. It may be a little different, but its decipherable. And once you realize how much more of the world speaks English, or how much communication can be nonverbal, it only gets easier. But if this is a hang up, and you know it, then choose an English-speaking location to make it easier on yourself.

If its getting lost or operating in another currency, my favorite response is: “there’s an app for that.” Concerns regarding accommodation – is this hostel a party hostel? Is this hotel in a safe neighborhood? – can be alleviated with research. We live in a different age – customer reviews drive much of the tourist industry, and this can all be researched and compared prior to booking. Identify your fears, and then do your research. Many will be alleviated by making the unknown known.          


Most people have an answer to one or more of these questions. You really just need an answer to any one of them. After that, a brainstorming session followed by a bit of research to narrow options back down usually results in a great travel plan, or a manageable few to choose from.  And once you do it once, it gets easier. And the time after that – easier still. I’m proof of it: my first stop on my long trip was Mexico City. I had screenshots and specific instructions on exactly how I wanted to get from the airport to the hostel, mapped out and noted and practically memorized. A bit of construction through me off track, but I had all my resources. By the time I landed in my last foreign airport that would require navigation to a hotel, in Ho Chi Minh City, the travel plans unfolded a bit differently. I received a friend’s text while waiting to de-plane, asking if I had landed. “Yes,” I replied. “Now to just figure out how to get to the hotel.” Did I arrange a transfer? No. Did I know if there was a shuttle? No. Did I have a map? No.

  Moonrise from a rooftop in the medina ~ Tangiers, Morocco  Moonrise from a rooftop in the medina ~ Tangiers, Morocco

I did know this: airports tend to have taxis, and I had the name of the hotel and the address written down. I did a quick check to see if I could determine what a taxi should cost, and off I went. No maps or screenshots or notes or planning. Because after five months, there was a comfort level with the situation – it was no longer unknown.

In other words, just keep going, until you wake up at the end of a flight, and have to check your ticket to see what city you’re in, and just go from there! But in the meantime, there are hundreds of ways to prepare yourself. You may not be able to predict everything, or make every uncertainty vanish, but you can arm yourself with a great deal to help navigate a new terrain.

Happy planning!

With curiosity and courage,


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