Planning a Trip Around the World – Part 1 – First Steps

I’ve been meaning to do this blog post for a year and a half now, and have finally gotten around to it.  With the world at a standstill right now, perhaps people are fantasizing about the day when they can travel once again.  Maybe you are thinking of taking an even bigger leap and taking an extended period of time to travel to different parts of the globe.

If you are considering such an adventure, this series of posts is meant to be an introduction and give some lessons I learned and that I wish I had known before I embarked upon my adventure.  It is by no means an all-inclusive guide.  It is simply some general ideas and tips.

Step 1: Start reading about trips around the world and similar long term travel. 

This is the learning and dreaming stage.  You’ll be taking this from abstract idea a bit closer to concrete reality.

The research can be in the form of books, articles, or online.  One book I read early in my thought process of this was By Men or By the Earth by Tyler Coulson.  It was about a young man who decided to walk across America.  I had come across a free electronic version of the book, and it was OK, but nothing special.  Yet it did help give me some insight into the emotional toll of such a journey.

About a year and a half before my trip as I began to get serious about it, I bought The Rough Guide to First Time Around the World.  This book was extremely helpful on a lot of the practical aspects of planning such a trip.

As I got closer to my journey, I found that was a great resource.  The creator of the site, Matthew Kepnes, has been consistently travelling for about ten years.  It also has a much more inclusive guides and detailed articles on the subjects I just briefly touch upon here like finances and medical insurance among many others.

Maybe at some point, I’ll finally finish my own book on my journey, then you might be able to add that one to the list … you never know.  Or you can always go back and look at my past blog posts….

Step 2: Begin formulating some big picture ideas of your journey

This doesn’t have to be any detailed planning, just some slightly more specific idea of what you envision your specific journey being.

How long will you travel?  Will it be one long trip of a few months to a year or so?  Or will it be an open-ended lifestyle where you spend months on the road and then return home for a short while at a time?

What kind of a budget will you have on your trip?  Will you try to work as you go?  Will you work locally where you visit or will you be a digital nomad, working remotely or freelancing?

Will you not work at all and simply travel?  Or maybe you’ll study?  Or perhaps volunteer like I did?

It will likely be some mixture of all these possibilities that is unique to you.

Step 3:  Start looking for specific opportunities that fit into your idea and begin making arrangements

For me, this was the stage where I found the YMCA Prints of Hope program in Colombia (now called YMCA COLead3rs).  I knew I wanted something where I could work and earn a little bit of money, and I was in the process of my nonprofit management program through UCLA-Extension, so I wanted to work in the nonprofit sector. This program was the original building block for my trip.

From there, there were certain aspects of the journey that I also wanted to include.  I wanted to hit all seven continents; I wanted to do an ocean crossing on a sail boat; I wanted to volunteer in a variety of sectors; I wanted to take some unique classes, like Kung Fu at the Shaolin Temple in China.  These general ideas helped me to begin to formulate some ideas and plans regarding my plan of travel.

However, it is important not to over plan and have a tight and rigid schedule.  Because things will go wrong and change.  So being flexible is critical.  You might misread the visa requirements for your connecting flights through Venezuela, and be stuck in an airport trying to rearrange flights at the last minute.  (cough)  Or realize that your passport if filling up and you have to get a new one and then need to extend your stay in a country while it is getting processed (cough, cough).

As you travel, you’ll also learn about new activities that you want to try.  Or you’ll learn that as you plan your travels, you’ll be in a location around the time as a big festival, so you’ll want to arrange your travel to hit that.  Maybe you’ll already be in Europe in the fall, so why not hit Oktoberfest or something.  In my case, I realized my travels would have me in Asia in the January and February timeframe, so I arranged my travel so I would be in China for Chinese New Year and in India for Holi a few weeks later.

Here are some programs that can help you find different work and volunteer programs.  Going through a professional program can help with paperwork and visas, while going through a matching program like Workaway is cheaper.

International Exchange of North America


International Volunteer HQ



Step 3: Classes and Workshops for Needed Skills

This is something I really didn’t do, but I wish I had.  This might be done far in advance, or just in the last few weeks before you leave (or even during the course of your trip).  However, depending on the type of trip you want to take and what you want to do, it might be beneficial to start taking some classes or attending some workshops well in advance.

For example, if you are going to be spending a significant amount of time somewhere that speaks a language you aren’t fluent in, it would be good to at least take a beginner’s course.  In my case, the majority of my time was spent in South America.  Luckily, I’d already studied Spanish, but in the last few weeks before I left, I was watching Spanish-speaking shows, listening to music, and going thru Duolingo.

I wish I had done an introductory photography workshop prior to leaving.  I didn’t think at all about photography until my trip to Antarctica, halfway through my journey, when there were a couple of workshops on the ship.  That opened up my eyes, and I think there is a definite improvement in my photos and videos after that trip.  A simple one day workshop before I started my journey would have likely meant far better pictures and videos from my time in South America.

If you are considering blogging or travel writing or trying to get followers on Instagram, you really need to do some research and look into the details.  I had it in the back of my mind that I might try blogging for a wider audience, other than family & friends. But after meeting people during my trip that actually did do that kind of thing, I realized how involved it really is.  So if you’re considering it, make sure you do the front-end work and prepare yourself.

It also would be a good idea to look into a basic self-defense or personal safety class, especially if you can find one geared towards travelers.  If nothing else, at least research some tips and tactics online (which is what I did).  This is one of those skills you hope you never have to use, but it’s better to be safe than sorry.

How early or late you do these classes and workshops will vary based on your specific needs and your starting point.  And some of them can wait until the trip itself.  I wanted to learn to SCUBA dive, but I decided it would be pretty awesome for my first time to be on the Great Barrier Reef.  Which it was!

Step 4: Begin making work and financial arrangements

Eventually you will need to figure out what you will do regarding work, assuming you already have a job.  Will you take a leave of absence or sabbatical?  Will you be able to work remote?  Or will you just quit?  (I quit mainly because they would only give me a three month leave of absence and I kind of wanted to be open-ended.)  However, I also delayed my trip by six months because I knew I had a promotion and raise coming soon, and I wanted to take advantage of that for both financial and career reasons.

Financially, there are a lot of arrangements that should be made well in advance.  I started about 2-3 months before I left, but I should have done so long before that.

One recommendation I would make is to get a travel credit card as soon as possible, if you don’t have one already.  I got the Chase Sapphire Reserve card and the bonus points for signing up as well as the general rewards points were an incredible help on my trip.  My flights from South America to Australia (with a layover in New Zealand), and then from Australia to Greece (with a layover in Dubai) were all paid for with those reward points.  Additionally, a card like that will also cover Global Entry and TSA Pre-Check, so if you’ll be coming in and out of the USA, that is a great perk to have.  An even better perk was the Priority Pass lounge access.  This gets you into thousands of airport lounges around the globe.  Over my year and a half of travel, the amount of food, drinks, and WIFI I received in these lounges likely covered the annual fee of the credit card.

Other rewards programs (like hotel and airlines) are something else to get set-up.  I parlayed my Marriott points into occasional “luxury” nights during layovers.  So look for ways to take advantage of travel programs. When considering travel credit cards and travel rewards programs, The Points Guy is a valuable resource.

Another financial consideration will be to open a checking account with an ATM card that has no foreign transaction fees and no ATM fees at all.  I use the Schwab Investor Checking Account.  Trust me, it is such a relaxing feeling when you don’t have to worry about insane fees.

One related financial/legal consideration that I did, and am extremely glad I did since I knew I wanted to be out of the country exclusively, was working out an arrangement with my dad to grant him Power of Attorney.  This is something that I don’t remember reading in any guide, and I don’t remember how exactly how we came up with the idea to do it, but assuming you have someone you trust almost completely, I think it is a wise decision.  If something bad would have happened to me, it would have granted my father more power in dealing with authorities and with my personal affairs than he would have simply as a parent.  He would have been able to file my taxes for me if I wasn’t able to.  The one aspect where we did utilize it was when I needed him to complete a significant financial transaction for me while I was in Peruvian village, with no way to submit legal paperwork.

As part of this deal, we also set-up a joint checking account.  This way, we could easily transfer money in and out of that account, and to each other without dealing with wire transfers and the like.

(Along with the power of attorney, if you want to be truly prepared, even if you don’t want to think about this, a last will and similar planning would be smart as well.)

A final note on the aspect of financial items, it is also critical to have spare cards and accounts to be safe.  This was one where I was extremely glad to have done this.  I was pick-pocketed in Bogota the day before I was supposed to go on a trip to the coast.  It was going to take a few days to get the replacements.  But luckily, I had spare cards.  So other than putting me in a bad mood for a couple of days, it didn’t really affect my trip to the coast.

Step 5: Other long-lead logistical items

Aside from work and finances, there are some other tasks you need to take care of long before your trip.

Get the 52-page passport.  Regular passports are 28 pages, and you can no longer order extra pages after the fact.  This oversight led to me not being able to go to Victoria Falls, and instead had to scramble to find a new project to stay in Kenya for four weeks instead of the originally planned two.

Similarly, make sure you check on any visa requirements for countries you want to visit.  The timing of these can be tricky.  Some visas you can only apply for in a certain window before your trip.  Other visas can only be applied for in your home country.  These can cause bureaucratic headaches, so you want to have a handle on this in advance.

Vaccinations are critical.  Some vaccinations are spread out over a period of months and if you don’t start early enough, you might end up trying to find your second Hepatitis booster in a country that doesn’t have it (cough). That being said, it can be cheaper to do some vaccinations in other countries.  I got my yellow fever and rabies vaccinations done in Colombia because they were significantly cheaper than doing them in the USA.

Similarly, medical insurance is another critical need.  There are many options for global health insurance for travelers and many resources to find out information.  A couple of important points though.  First, your credit card might have travel insurance, and it might cover some very specific medical expenses, but it is not the same as regular medical insurance.  Secondly, these travel medical plans are not as comprehensive as your standard medical insurance, with a large list of exemptions.  These are mostly geared to cover you for sudden sickness and/or accidents, not regular medical care.  Although the plan I had through IMG Global did include some preventative care, such as a routine physical, AFTER I had been covered for a full year.  But they only covered some of my tests.  So you need to be careful and read the fine print of these plans.  The process of getting insurance may take a while, as you might need to get approval and give them medical records.  Therefore, get started on this rather far in advance.

Next in Part 2: What to Bring

In the second part of this “guide”, I’ll go through a packing list.  This will be as your trip is getting closer, within the next couple of months, and you need to start gathering your gear for your adventure.