The 12 Most Common Questions I Get About Traveling the World (Part III)

I’m no longer going to every country in the world (mission accomplished), but I’m still traveling at least 200,000 miles a year.

As such, I get a lot of questions over and over, both from people who want to travel far and wide and those who just want to learn a few things to make their lives easier.

This series of three posts provides some attempted As to the Qs. This is part III; here’s part I and here’s part II.

  • When using points or miles for flights, how far in advance do you have to book?

The best answer is “it depends,” but of course that’s not helpful on its own. The factors it depends on include the airline you’re hoping to fly on, your specific destination, season, and class of service.

Here are some general points that may help:

1. A lot of award seats open up as travel approaches. This is especially true on some of my favorite airlines and routings. Cathay Pacific First Class, for example, is hard to book in advance, but very regularly shows up within a week of departure.

2. If the airline agent says there’s no availability, make sure that he or she is really looking for it. Ask them to search segment by segment. Ask if they’ve checked all available partners. Ask if they have any other ideas. Lastly, if you’re not getting the answer you think you should, hang up and call back. It may just be a question of reaching a more helpful person.

3. In some cases, you may be successful convincing an agent to open up availability when there isn’t supposed to be anything bookable with miles. This outcome is more likely when you just need a single segment to complete your trip. Having elite status also goes a long way in getting exceptions like these.

  • Where should I stay?

In 15 years of regular, active travel I’ve stayed in all sorts of accommodations: hostels, guesthouses, strangers’ couches, and no shortage of airport floors, to name a few. These days I’m more of a hotel loyalist, especially with Starwood and Hyatt (and to a lesser extent with Hilton and IHG).

When you’re first starting out, you have a lot of options to choose from. To start with the above:

Hostels or guesthouses: check or

Independent lodging: check

Strangers’ couches: check

Hotels: check directly on the website for the hotel chain you’re interested in, or search for independent hotels

(Tip: if you care about loyalty programs, don’t book chain hotels using or similar agencies. You won’t earn benefits or nights toward elite status.)

  • What is your #1 recommendation for travel and travel planning?

#1 recommendation for travel in general: do it! Take your first international trip (or your first major trip, wherever it is) as soon as you can.

#1 recommendation for travel planning: learn more about the world. Read the Economist. Get a map and become familiar with the major regions. Pick a few countries or cultures you’re interested in visiting.

#1 recommendation for travel hacking: if possible, get the Chase Sapphire Preferred card. It’s the single best credit card for both an immediate bonus and strong ongoing benefits. I use mine every day.

Bonus: Join the Travel Hacking Cartel or read up on Frequent Flyer forums to help with earning points.

Then, put all these things together and refer back to recommendation #1: do it!

  • What’s your favorite country?

I don’t have a favorite! Everyone asks, but I really don’t. If forced to pick a single country, I’d pick Australia, where I try to visit at least once a year.

But there are lots of other places I like, too. Among others: Hong Kong, Japan, Laos, Ghana, South Africa, Jordan, Macedonia, Lithuania, and the list goes on.

I mostly just like traveling. I like being in motion.

I also like planning trips almost as much as I like going on them. For me, travel is a lifestyle, and I have no plans to stop traveling anytime soon.


This concludes the series… but definitely not the traveling. Wherever you are, I hope you’re doing well, and I hope to see you on the road sometime!


Images: 1, 2, 3, 4, & 5

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