Travel, like life itself, is open to many different twists of fate and circumstances. Most of our lives we’ve been told, “If you fail to plan, you plan to fail,” which means that from the time we were young, we are “encouraged” to find a college; a trade; a career. Decide what you want from life, and work towards that end. This is most often tied to the world of retirement planning. “Put away 10% (or so) every month, let compounding do the rest. Then you can retire at XX years of age, and coast along until the end.” That was the Coventional Wisdom, and the world I was raised in, and also the mantra that I preached as a financial advisor, which was my career in my mid-20s.
I’ll not get into the wisdom of all that, since it does make sense and it (mostly) works. But, sometimes shit happens and your plans fall by the wayside.
Since this is about travel, I wanted to address the mechanics—the specifics—of deciding where to go—or not go.
When Kat and I started our journey in 2019 we had a rough idea where we wanted to spend our time, and that is the same place as many travelers-to-be: Europe. It’s close and we’ve seen the shows and movies, and many of the iconic highlights and cities are familiar to us. Since we spent 6 weeks in Spain and Portugal during the summer of 2018, Europe is where we started when we left California six months later. Six weeks in Spain, followed by six weeks in Italy. That used up our Schengen time, so off we went to Croatia, which was non-Schengen at the time. During the past six years we moved around between Europe, South America, Asia, and Australia, and as we are now past 70, we’re seriously looking at the longer term, bigger picture. For US it’s a balancing act between the Balkans and Southeast Asia, so those are the two areas we’re bouncing between for the forceable force. Aside from the obvious affordability factor, the other major directive is weather. We don’t do “cold,” and in our lives that means night temps in the 40s, daytime 50s plus, and NO snow or ice, or freezing temps.
We meet many new nomadics, and they ask us lots of questions, and we happily answer, since we love helping them, plus we ask our OWN questions of those that have answers to OUR questions. So I started writing down what I call “qualifying questions” to help narrow down the process of starting a journey, or options of how to move along in the future.
WHY do you want to travel?
This has a lot of nuances, and I thought back to a note I recently got from a widower who was about to take his first adventure. So I posed THIS question to him to find out his motivation. Sometimes, with the death of a spouse—or any life altering event—we want to jumpstart a new chapter in our lives. I mean, I did in 2013 after I exited a 27 year marriage, plus house ownership, and had to reinvent myself at age 59. Kat and I had Europe at the top, South America and Africa at the bottom, and a few other places in between.
WHAT do you hope to get out of it?
What are YOUR drivers? History? Culture? Food? Fun? There are no wrong answers here, nor to any of these questions.
What kind of things do you like to do in your downtime?
How “active” are you, or do you want to be? Are you an adventurer or a couch potato? For me, I had visions of riding a bicycle along the coast of Portugal when we fell in love with that country in 2018. Getting in shape, looking 20 years younger; those were my fantasies, which did NOT come true!! Aside from our COVID containment in Mexico, I did no bicycle riding, but was fortunate enough to find motorcycles instead.
What kind of weather do you like?
I know people who love cold weather! Go figure, it takes all kinds, but that ain’t MY jam at all! We’re Mediterranean all the way, similar to Orange County, CA.
How do you handle different trip lengths, ie, short distance jaunts, vs. longer distances?
I have cautioned this before: You do NOT need to jump into the travel pool with both feet, sell everything, and leave it all behind. There are scores of travelers who travel XX number of months per year, and they keep their old home—or maybe they have a room to stay at their kids or friends? There’s no hard and fast rule for ANY of this. Everyone goes where they go for a certain amount of time to “test the waters.”
Is your budget adequate to take you where you want to go?
The misconception of many in the non-nomadic world is that they think we are rich!! “What, did you win the lottery?” is a question we’ve heard countless times, and of course we did not. But we live comfortably on about $3,000 per month, and the rent on my old apartment in California is now $2,950. I checked.
What is your “end game” if you have one?
Are you looking for a second home? Many are, and some commit to that too prematurely without looking at their options!! You love Tuscany? Of course, but there are lots of options in Italy and outside the country. It’s important to not fall in love with your fantasy, and do your research.
Do you have reasons or obligations to take you back to your home country?
The Big Three: Kids, grandkids, or parents, are what keep many who wish to travel tethered to their home. And that is fine, they are all legitimate. In our case, none applied, so we had no restrictions.
How would/ do you support your lifestyle?
There’s few advantages to getting “older,” other than social security. For some, that may be enough, but for others, it’s not. And what about the fifty-somethings or younger? Financing travel is an open-ended conversation, and there are many options.
How does your age factor into your future?
Kat and I faced this from Day One, and we face it even more closely now: We only have a FINITE amount of time to travel as we have. Our plan for the future is having a place in Vietnam and Albania where we can keep some “stuff,” and allow us to travel a bit lighter.
So, there you have it. A self-analysis test PRIOR to taking any travel adventures. And these questions apply to all nationalities, not just Americans.
We’re coming up to the Last Quarter of 2025; it’s not too soon to start planning for next year! Need help?? Let me know.






