by Rock Earle, Founder Chief Executive Officer, ROX Group, LLC

Huh? What on earth is F.I.T.? F.I.T. is an acronym that can stand variously for Free, Frequent, Foreign, Fully, or Flexible Independent Travel. What it really means is a tourist or tourists travelling independently, designing their own itineraries and making their own travel arrangements without being part of any group or imposed schedule. Yes, travel agents can certainly help with the actual bookings, but in your mind and on the ground, you’re on your own.

F.I.T. Travelers by definition have bigger everything than group or tour travelers: bigger tolerance for change, uncertainty and the possibility of disappointment (bigger brains?); bigger budgets (maybe bigger bankroll?); bigger interest in surprise (bigger curiosity?); bigger need for intensity (bigger bandwidth?) and bigger distaste for human herding behavior, but most of all, a bigger desire for serendipity (bigger hearts?).

But just what, actually, is serendipity? We hear it all the time, and it sure sounds good. According to Wikipedia, serendipity means a “fortunate happenstance” or “pleasant surprise”. It was coined by Horace Walpole in 1754. In a letter he wrote to a friend, Walpole explained an unexpected discovery he had made by reference to a Persian fairy tale, The Three Princes of Serendip. The princes, he told his correspondent, were “always making discoveries, by accidents and sagacity, of things which they were not in quest of.” In the travel world, F.I.T. is how you get that.

So, as the wisdom of the years piles up, I have learned to get comfortable – maybe even a little intimate – with a little uncertainty. Of course, not with regards to my airplane seats, but if everything always turned out as expected, where would the fun be in that? I like to call it the “Oops!” factor.

Like going without hotel reservations and driving up to the only hotel in sight at the end of a long driving day in foreign territory, with no choice but to spend more than you ever thought possible, then you say “yes” and the room exceeds all of your expectations, and you regale your friends with stories for years.

Reservations? We sneer at reservations!

Even with reservations, as a (prematurely, as it happened) confident young man, I once strode confidently into a quite nice hotel in Munich on September 12, just in time for my first visit to Oktoberfest, after having nicely freebooted about Europe for several days. For what was to be a three-week road trip throughout Europe, these were the only reservations I had bothered to make in advance, such is my respect for the attendance to this event.

So, imagine my surprise when the desk clerk, upon hearing my name, frowned and shook his head: “Sorry, we have no reservation for a Mr. Earle for tonight.” Oops.

Me: “How about Mr. Rock?”

He: “No, no.”

Me: “Ummm … “

He: “Ahhh … I see … [you stupid Amerikan] you have made your reservation for December 9th.”

Me: “Ummm …”

Get it? Yes, our 9/12 is their 12/9, and yes, it was my fault. And, everything turned out okay after an initial minute or 10 of tremors, shock and fear. Of course, the internet and hotel booking engines have largely mitigated that particular risk now, but this was back in 1997 – before GPS, Google maps, smartphones and, of course, data roaming – decidedly pre-Anthropocene.

In other F.I.T. tales, imagine taking a ferry to a tropical island off the shore of Tanzania, only to find that there is no actual dock. Passengers wishing to disembark must do so into the water at their destination, with whatever paraphernalia they carried. That particular situation didn’t happen to me personally, but it did happen to someone I know, and it certainly could have happened to me.

Or imagine missing the connection to Jakarta in Tokyo one evening (Grrr!) only to be handed a voucher for a wonderful hotel room and a ticket for a flight out, nice and fresh the next morning – a much more satisfactory arrangements of seats, beds and toilets than we would have arranged on purpose.

Or consider the food place in the Rome airport where we recently ordered rice bowls; take-away turned out to be permitted for rice, but not beef, so we just ate in the lounge – where’s the fun in that? Not to mention our guide in Tuscany, who said not to bother going to San Marino or Rimini. So, on a “free” day in Tuscany, that’s exactly what we did. She was right about Rimini, but oh so very wrong about San Marino – it was spectacular and well worth our effort! Just one more example of why we always do the opposite of what we are told, by friends, co-travelers, guides and people who should know, but non-prescient and with no relationship at all to whom we like to refer to as the “Travel Gods”.

Speaking of Guides – sure, hire a guide every now and then? They’re just like everything else. There are good ones and bad ones, but the bad ones provide more grist for the storytelling mill, and you will eventually come to cherish even the expensive wastes of time.

Most people we talk to desire trouble-free travel and will go to great lengths to get it, like traveling on a bus in a group with a guide. But the more you plan, the fewer chances there are for mess ups, and lesser still the possibility of serendipity. But with the right demeanor everything is enhanced on F.I.T. – even the, shall we say, mistakes, which there will be, of course. These are the things no one could possibly plan for. And some things, you could have.

So, when people ask us how our vacation went, we bite our tongues, because F.I.T. isn’t really a vacation! Sitting on a beach, or in a boat, or in a spa is; the conscious act of pushing one’s awareness into foreign realms is decidedly not. Really, the actual act of travel itself is NOT anything resembling a vacation – it’s just work. Or as I like to think, if you can grow by the experience, it ain’t a vacation. Sounds like F.I.T. to me.

For me, the greatest enjoyment of travel is the remembering and recounting of the actual adventures, followed closely by the ideation and imagination of a journey. In my case, at least, memories are always embellished – bad becomes good – or poignant, at least, and usually funny in the retelling, and good becomes great. Absent bodily injury or extreme financial pain, what’s not to love about a little uncertainty that could lead to challenging circumstances which give rise to timeless and viscerally funny stories? I don’t particularly care for traveling – it’s just hard work – but I love having traveled.

And, for sure, this type of “serendipity” happens to even the most experienced travelers, even after 75 countries, which, for me, is the driver to continue on to 85!

So get on the internet, take a deep breath, buy some tickets and give chance a chance!