NEW: Check out my exclusive NFT travel photographs for sale.

Travel With Bender

Uncovering the best vacations

Living The Dream

Living The Dream: Giving Away Everything To Make It Happen

I have met Kerwin several times over the years and he is a airline geek with the softest heart. He left his airline job over 4 years ago and has been travelling ever since. So how does this gentleman make Living The Dream work for him?


Kerwin McKenzie

What was the first country you visited? Who with and why did you choose it?

In 1985, I visited Martinique in the French Caribbean for 17 days as a French Exchange Student; on my way back to Jamaica we stopped in Haiti. I had to speak French the entire time I was there; on the last day, the kid next door told me that my host father is an English teacher. I always wanted to get on an airplane and go somewhere so when that opportunity came along I jumped at it and my parents supported it.


When did you start a travel lifestyle? What inspired that change?

I've been traveling for as long as I can remember. I'm an aviation geek so travel comes with that territory. Full time travel started in June of 2011 when I left my airline job of 14.5 years. The company was merging and all the planets aligned, well, almost all of them. So I gave away almost everything I owned, rented a car with the rest and headed to a friend's house and have been staying with different friends and families and hotels around the world ever since. I tell you, it's really difficult to give your stuff away and I've learned how much my friends and family really means to me.


Do you have a base you travel from? Or is it continuous travel? And why do you choose that style?

Houston, Atlanta and New York are kind of my bases, but I flip flop all over. I literally have friends all over the world so that makes it easy. Ever so often I do a continuous travel like at the time of this writing. I chose the lifestyle as I hate to be in one place for too long. For me, its all about the journey, meeting new people, talking with them, finding out what makes them tick. Oddly enough, without asking almost everyone I meet in my travels invites me to their house the next time I'm in their city; its very strange and I've not been able to figure out why they do this. Most recently was an American couple I met at my hotel in Jerez, Spain.


How do you fund your travel lifestyle? Is it something you do when travelling or are you a saver?

The big question huh? It's tough, but for some reason I make it happen. Its a combination of savings (I'm a terrible saver so there's not much there), 401K, severance pay, ebook sales, income from my blogs and consulting. Staying with friends and family is a huge part of the funding as well.


If you could tell yourself one tip before you started your travel lifestyle, what would it be?

You know, I wouldn't change anything. My life is already recorded, I'm just playing it back.


What does "Living The Dream" mean to you?

The ability to not know what's next. Being able to stay in a place as little or as long as you need to and then choose a mode of transportation, air preferably and go. Plus being able to help others as they need it and you are able. I'm a simple guy; I don't need much.

You can find Kerwin McKenzie here -

Website: Cruisinaltitude

Twitter:  @mskonfa1990 

I'm a bit of a crazy traveler. I worked in the airline industry for about 16.5 years and now I create travel solutions for travelers. I live life beyond the fullest and enjoy every moment.

Here's what you have to say...

"I respond to every comment by private email. So please leave me comments, I love chatting to you" -
Posted by nicole on
Yay, awesome Kerwin! Met some really cool travelers over the past few years and you're one of them :-).
Posted by Heidi Wagoner on
So that is who Kerwin is! :-) I see his name all over in the various facebook groups and now I feel like I know you a little. Isn't the life of travel wonderful? We set up our home base in Spain, but we did live in North Carolina for 12 years, so not too far from your home base options. I love this interview series Erin.
Posted by Kerwin on
Thank you Niclole, the feeling is mutual; you have a calming spirit.
Posted by Kerwin on
Hi Heidi, that's me :-). Yes, the life of travel is a very wonderful thing. With technology you can do anything from everywhere.
Posted by Online Toy Store In Australia on
Great post ! thanks for this share.
Write a comment...

Please DO NOT include links/URLs or HTML in your comments - they will be automated deleted and you will waste your time.

(Your email will not be publicly displayed.)
Find more posts by tag:

Reader FAQs:

Question: How can I create my own travel blog?
Answer: Read my super simple step-by-step guide that will get you online in 5 minutes.


Get The Latest Blog Posts

There are a number of convenient ways to get the latest blog posts and news from Travel With Bender.

RECOMMENDED: Want to find out how the travel pros spend their money overseas without the big ATM fees? Wise (formerly TransferWise) is the answer. You can also use it for super low-cost international transfers (way cheaper than banks).