Then and Now: The Evolution of My Travel Philosophy

My obsession with points, elite status, and the search for bigger and better airplane seats and hotel suites sometimes draws good natured criticism from friends and colleagues. Understandably! But what many don’t know is that I didn’t start out craving the nicest rooms.

I first started traveling in the early 2000s when I studied abroad, for all intents and purposes my first time out of the country. I was deal savvy then but more interested in going and doing than making sure things met a minimal standard (and apparently safety).

• Jumping on opportunities mattered more than comfort.
  I found £5 Ryan Air flights to Ireland that required sleeping in the airport since no public transportation started early enough to get us to the airport. I took flying solo trips to Scotland where the cheapest fare landed me back in London too late to catch the last train back to my dorm and had to sit up all night in a freezing cold train station with no bathroom access.
• Weather and travel time were irrelevant.
  Entire weekends would go by where we were never quite dry or warm (thanks to England’s winter rains) and heavy backpacks had to be dragged everywhere we went. I won’t even talk about figuring out intricate bus routes in order to visit less popular churches or cathedrals we heard were worth a visit (they rarely were).
• I assumed hostels were the best/cheapest options.
  And found myself in situations I wasn’t quite comfortable with and I’m sure my parents wouldn’t have been either — booking accommodations with a guy at the Rome train station and discovering it was a room in his house with 2 bunk beds and 2 other occupants (probably an early Air B n’B). I remember plenty of sheets and pillowcases with stains and perfume smells that suggested they might not have been washed recently enough. The co-ed room where one ill traveler shouted graphic obscenities in his sleep. And of course the place in Paris where the bar attached to it had a stabbing the first night we were there.

That’s not to suggest I didn’t have fun! I did. I was just slightly uncomfortable and anxious the whole time. So when after that Paris stay we found a 1* hotel that was as cheap as our hostel with the stabbing but way more comfortable, it began to change my perspective on things.

I had more fun when I could have a private shower, leave my luggage, and be guaranteed not to share a room with anyone I didn’t know. And as I acted on this, I realized that my comfort and enjoyment increased as the quality of service did.

So a little more than a decade later, here’s my current travel approach:

• I jump on opportunities immediately.
  If anything, more quickly than before, but now I know to do a little more research on weather, timing, and other costs before pulling the trigger or passing the 24 hour cancellation period.
• Planes and hotels are often the destination in themselves.
  My reasons for travel have evolved. I still like to go and do, but I’m more about the overall experience. And let me tell you — flying Thai Airways First out of Bangkok on the A380 is just as exciting and eye-opening to me as seeing Jim Thompson’s House. And Koh Samui’s beauty very well might be best seen from my private infinity pool at the Conrad.
  
• I have more capacity for enjoyment when I’m not uncomfortable.
  I pretty much will never stay in less than a 3* hotel these days, but that’s because I paid my dues in full! I don’t want to worry about safety, about bed bugs and clean sheets (which isn’t guaranteed even at 3*’s), and about lugging along non-wrinkling clothes or all my own toiletries.
• If I like it, I will come back.
  I’ve proved this over and over to myself. By not trying to see everything in a 16 hour day, I can actually see more because I’m up for traveling almost every weekend and the last trip didn’t exhaust me.

Miles, points, and sites like Hotwire and Priceline have made it easy for my travel philosophy to evolve, and I’m not actually spending that much more on any one trip. I just take a lot more trips. 🙂

What about you? Has your travel philosophy/approach changed over the years?

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