How to Plan a Trip Around the World

People are understandably curious about the logistics involved in an extended trip around the world. How can you afford this? How do you get so much time off work? What are you going to do with your house?

And then there are the questions about the trip itself: How did you decide where to go? How in the world do you pack for something like that? Aren’t you worried about safety?

There are no easy, straightforward answers to these questions. Travel planning, just like life itself, takes many twists and turns during the journey before the journey. So, despite the solutions I share here that have ultimately worked for us, you may find that your planning involves a very different path. Regardless, it’s good to hear about the mistakes of others so that they can be avoided.

Since these topics can become a bit complex, I’m going to break them into separate posts: The Route, Money Matters, Timing Is Everything, Getting Documented, Staying Safe and Healthy, and How to Pack for the Entire World.

For me, the route dictates everything else. Plus, it’s fun, and I want to start this series in a positive way before we talk about the dual stressors of money and time.


Our 2018-2019 around-the-world itinerary

How to Plan a Trip Around the World: The Route

Angela and I started with the goal of actually circumnavigating the globe. Since we live much closer to the east coast of the United States, it required very little discussion to decide we would proceed east toward Europe as opposed to west toward Asia.

Our original route was little more than a beeline of long flights, skipping from the U.S. to central Europe, to Dubai, on to western Asia, and returning to the U.S. through Los Angeles. It was going to be a two-week whirlwind that would have left us exhausted, jetlagged, and ultimately dissatisfied.

Wanting to maximize time and economy without sacrificing the experience itself, we reset our priorities and struck upon the following:

Fly one-way in all cases. I’ve already talked about this in a previous post and can testify that it works. Our trips to Australia and Ireland incorporated one-way travel as much as possible and afforded us some experiences that we would have missed otherwise. Without traveling one-way, we wouldn’t have made it to Brisbane or Isle of Man, two destinations that turned out to be some of our most memorable.


Without flying one-way, we would have missed the “Winkie” lighthouse on Isle of Man, UK

In planning this trip around the world, one-way travel is proving crucial.

I toyed with using major airport hubs and round-trip flights at one point. I actually crunched the numbers and made the comparisons and found that, with a series of round-trip flights, the time spent in airports would nearly double! Plus, it was not cost effective. By flying round-trip, not only were we spending more on airfare itself but also on airport transfers, hotels, and overpriced food in close proximity to the airports.

No, thank you.

Pair the cheaper one-way flights with the opportunity to see and do more, and this one is a no-brainer.

Use driving loops for a more authentic experience. This stands in stark contrast to my rule about one-way flights. Although I would love to rent a car in one location and drop it off in another without having to double back, that becomes cost prohibitive with rental cars. Most of the time there is an exorbitant fee associated with dropping a rental off at a different location. I do, however, check this before I commit to renting a car, and, on occasion, I have found rental companies that will allow drop off at a different place for no extra fee. When I do, I take advantage of that opportunity to keep moving forward.


Sometimes the rental car is not a car

I began building driving loops into the route but also wanted to avoid driving in major metropolitan areas when I could. The best airfare, however, is typically between major cities, so I started looking for destinations based on two criteria: major airports located on the outskirts of the city, yet with close proximity to country borders. That way, we could affordably visit the cultural center of a city via public transportation and also rent a car at the airport, avoid the majority of the metropolitan traffic, and drive across country borders for vastly different experiences.

Barcelona and Krakow both fit those criteria, but Vienna has served as the model for my search. Located outside the city circle, Vienna’s Wien-Flughafen Airport is only an hour’s drive away from Hungary, Slovakia, and Czechia.

Four countries with only one flight and a couple days of driving is pretty hard to beat!

Our most enjoyable travel experiences typically happen outside the major cities and certainly outside the tourist districts. And, admittedly, I love to drive in a new place. The freedom, the local flavor, and the easy pace is only possible when you’re in control of your own vehicle.


Our new Libyan friends and bunkmates met on the overnight Moroccan train from Tangier to Marrakech

Travel between like-minded countries whenever possible. This one takes a bit more research when it comes to politics and religion, but the extra effort is worth it. Even in western Europe where borders are typically open and easy, you can still take advantage of territorial associations to save money on travel.

For instance, the Azores Islands are a Portuguese territory just west of the Iberian peninsula. One-way flights from Madrid, Spain, will cost about $120 USD and typically have at least one layover. But one-way flights from Lisbon, Portugal, on the same day are nonstop and cost just $90 USD.

Now, take the same two originating airports, Madrid and Lisbon, but check one-way flights to the Canary Islands instead. Although the distance to the Canaries is roughly the same as the distance to the Azores, the price differences are flipped because the Canary Islands are a Spanish territory ($90 USD from Lisbon, but only $30 USD from Madrid).


The view from our Airbnb villa in the Azores off the coast of Portugal

The savings become even more obvious when you look at territories that are truly “overseas”. One-way flights from Madrid to Nador, Morocco, carry a hefty price tag of $240 USD, but you can fly to the Spanish-held city of Melilla just up the coast of Morocco for half that price.

In the Middle East, flights between two predominantly Sunni countries will typically be lower than flights between Sunni and Shia countries. And, if you want to go island hopping in southeast Asia, try to fly from an Indonesian territory to another Indonesian territory, and do likewise for the islands of Malaysia.

But there are other, more subtle, benefits to making related territories points A and B on any travel segment. In particular, customs and immigration processes run more smoothly when you are traveling between like-minded stops. And, you will exchange currency less often, saving you the invariable surcharge there.

Build rest days into the schedule. I know this may seem ridiculous to include in the plan for what is essentially a vacation, but rest is critical to maximizing both enjoyment and productivity on a trip like this. Previously, I have made the mistake of pushing too hard and traveling too quickly. There is nothing worse than having actually visited a place but being too tired to remember the experience.

In planning this trip, I was sure to periodically build in multiple days at the same location so we could occasionally unwind and (gasp!) sleep late in the morning. Moreover, at least once a month, I have included a week in the same location. Although we will be taking day trips, returning to the same bed every night will provide its own kind of respite, giving us a chance to do laundry, edit photos and videos, and catch up on the inevitable writing backlog.

Be willing to forego the typical destinations. Many of our foreign friends count a visit to New York City as “seeing the United States.” And, while this is technically correct, I would be reluctant to say that New York City can give an authentic experience of what it’s like to be an American. Thus it is with Paris or Cairo or Shanghai.

Although I’ve always wanted to visit Prague, Czechia, we are going to opt for a trip to Brno instead since it falls within the scope of our Vienna driving loop. From the minimal research I’ve conducted, I don’t believe the city will disappoint in the least.

And, although I’m a huge fan of Game of Thrones, we are going to purposefully avoid the tourist throng in Dubrovnik, Croatia, and spend time exploring the smaller towns around Split as an awesome consolation.

We will skip the typical “must-do” Kenyan safari and get our fill of wildlife in the wonderful game reserves of Botswana, Sri Lanka, and Nepal. Instead of swimming with jellyfish in Palau, we have found a lesser-known island off the coast of Borneo that provides the same experience.

A herd of elephants viewed on safari in Botswana’s Chobe National Park

Perhaps we will miss a few iconic photo opportunities by avoiding the major tourist destinations, but we will also miss the crowds and inflated prices.

And speaking of prices …

Next up — How to Plan a Trip Around the World: Money Matters