NOTE: We are not advocating mass travel during this time, but we do want to continue to support the incredible businesses and destinations that make this world so amazing. However, we do encourage you to virtually travel through our articles and plan your visits for when it is safe to do get out there.
Interview with Charles McCool on Being a Happy Traveler

People Who Travel: Charles McCool on being a Happy Traveler

Affiliate links linking to products we love may be found within this article. For more info, please check our Disclosure page for more explanation of affiliates and sponsorships.

Everyone wants to make the most of their money when traveling and Charles McCool has mastered this. He looks beyond simply travel hacking one’s way to savings and wants us all to become happy travelers. Aside from having one of the coolest surnames, he is literally one of the most interesting people you’ll ever meet. Thankfully, I got to hang out with him last year during our Fathom cruise. I wanted to find out more about his methods, thoughts, and gather any advice that I could for you—and myself. So let’s see what the happiest traveler on the planet had to say when I threw five questions at him.

People Who Travel: Charles McCool

on Being a Happy Traveler

Charles McCool in Budapest

What does it mean to be a Happy Traveler? 

Being a happy traveler is different for every person. Some people want a catered experience, staying in first class lodging, ordering room service, enjoying the spa, but never leaving the property. Other people do not care about where they stay because they want to explore every street and alley. Some travelers want to cover a lot of territory when they travel, while others want to immerse in one place and really understand it. And so on.

Furthermore, a single individual has different purposes depending on who they travel with (solo, partner, family, group, friends, etc.), how much time they have, and more. I know I do! As a travel writer and teacher (I taught travel skills classes for 8-10 years), I consider it my job to present trip-planning tools and information in such a way that people can craft their own trip. I like to say that I empower happy travelers, giving them what they need to travel how they want. I do not like the articles that shout at me: 10 Must-See Things, 10 Best, 36 Perfect Hours.

When did you want to become a full-time traveler?  

Definitely when I was in college but a mentor convinced me to finish up and get the degree. He said I may never go back. Truth. Various life stages have occurred since but a year ago, I made the decision to leave the latest cushy cubicle gig in order to travel as much as I can. I once spent a solid 16 months on the road (over 20 years ago), which was my longest full-time traveling stint.

Charles McCool Wynwood

Who inspires you as a full-time traveler? 

So many. Shane Dallas (The Travel Camel) is an Aussie who now spends all his time in Africa. Sherry Ott (Ottsworld Travel Blog) is a brilliant photographer who recently went to remote northern Canada and is always on the road. Alyssa Ramos (My Life’s a Movie) always seems to be in some exotic place. Scott Eddy (Mr. Scott Eddy) has crafted a lifestyle where he can travel anywhere in the world for as long as he wants (and often does). Amy McCool (not directly related) lives in a van with her dogs and roams the US west. Rasheed Hooda is a vagabond in a van and recently walked Route 66 (yes, walked!). So many other modern day nomads made the empowering, difficult, but enlightening decision to see the world on their own terms.

What’s going on in your travel writing/blogging/whatever you’re doing career right now? 

I do not like to stick to a formula, never have in anything. The blog posts that essentially say do this because it worked for me are not for me. Just like those travel articles shouting that you must see these things I did. I am just trying to be authentic and create a network of happy travelers. I have always enjoyed helping people take better vacations so I will continue to keep that as my focus. I still have aspirations of being the pioneer of a corporate travel wellness benefit program.

Heck, medical and dental are basic benefits, then some progressive companies offer financial and mental well-being support. Really progressive companies offer sabbaticals or travel stipends. I want to develop and provide the solution to the problem of US workers not taking all of their allotted vacation time (how crazy is that?). And those who do, I want their vacations to totally rock. See, “happy travelers“ makes sense, right? Someone should be the Happy Travel expert. Might as well be me.

Charles McCool in Iceland

Any advice you’d have for someone who thinks they can’t do what you’re doing?

Well, by now, you probably know I try not to follow other people’s formulas. I really do not recommend anyone do what I do and instead, do what they want to do. The world does not need another me but we do need for your brilliance to be shared. As for doing full-time travel, there are countless opportunities, most I which I have not yet even explored. Line up consecutive long-term housesitting gigs. Take your skills anywhere in the world. I know a software QA expert who works from Hawaii for a while, then South America, and then Asia.

I know other remote workers who specialize in web development, social media, writing, and photography. I know you and your wife taught English in South Korea. I love that. Again, there are so many opportunities that really the hardest thing is deciding to do something. The path presents itself once you did. It may not be the expected path but serendipity is pretty dang fun, too!

I really appreciate Charles taking time out of his busy schedule to answer these questions. I say he’s busy because he’s probably running a Twitter chat somewhere from @CharlesMcCool. You should also visit his site at and if you subscribe, you get to see just how prolific he is at interviewing travelers and writing about his journeys.

Charles McCool on the water

What do you think of Mr. McCool? Do you think you’re a happy traveler? Share your thoughts in the comments section below:)

2 thoughts on “People Who Travel: Charles McCool on being a Happy Traveler

  1. Julie at FuninFairfaxVa says:

    Great job capturing the Charles McCool happy travel philosophy! As someone who benefits every day from Charles’ strategies, I can honestly say that he has made me a more relaxed, efficient, and happy traveler.

    • Duke Stewart says:

      Thanks, Julie. You must have a lot of fun with Charles but I bet you have a hand in the planning, too, right? Love learning from you two and looking forward to seeing more about how to Travel Happy! Thanks for commenting.

Comments are closed.