Tripadvisor and the art of vacationing while going nowhere

I fondly remember my first staycation. I don’t mean crashing at a local Airbnb for the weekend, or stocking the house with wine and junk food and binging the last season of “The Crown.” I’m talking about a Tripadvisor staycation, where you go nowhere and do nothing, except in your own mind, where all-inclusive means just that.

I first packed my mental baggage to prepare for adventure in 2014. Back then, although I was a travel novice, I was a research expert. My girlfriend, now wife, and I decided that it was time to take our relationship to the next level. It’s a level that all couples are familiar with, an intermediate step between meeting each other’s friend groups and moving in together - going on your first out of town trip as a couple. My wife, whose amazing qualities would take too long to list, is not much of a researcher, so it was on me to plan this very important vacation, upon which perhaps the future of our relationship was held in the balance.

I had never looked seriously into vacation destinations before. My previous trips had mostly consisted of my parents driving my sister and I as far as they could in a particular direction before getting tired and stopping at a motel, hopefully near a national park or roadside attraction. By the way, the world’s tallest thermometer is located approximately 14 hours away from the Colorado state line, in case you were curious.

So with my mission in hand, I got online and saw this nifty looking website appear at the top of my Google search - Tripadvisor. Well, I was going on a trip and needed advice. I’d say I was their target audience. So, I clicked. And oh what Pandora’s box did I unlock.

First of all, I began looking up hotels in our chosen destination, which was no mean feat in itself. For one, our chosen destination was, broadly speaking... broad. We’d decided on Thailand as our first foray to test our mettle as a pair. This was a very scientifically determined destination, chosen because we were both 30 and had seen the film “The Beach” in our adolescence.  

Having that decided, where to start? Well, I assumed we’d be flying into Bangkok, so hotels in Bangkok, I guess? I imagined I’d get a handful of hotel names, maybe price ranges, a recommendation or two. Instead I got a list of five THOUSAND hotels, ranked by value. But wait there’s more! Insert mental infomercial voice here. You can also see listings based on traveler ranking, price, and distance.

And the filters! Oh, the filters. Are you perhaps looking for 4-star hotels for a hundred and ten dollars a night with included breakfast within 2 miles of downtown? Don’t worry, Tripadvisor has you covered.

Minutes turned to hours, and before I knew it I had a curated list of a dozen properties saved to a customized “trip” on my profile. And what’s more, I felt like I’d been to those places in that time. I’d lain in the bedding, I’d digitally swam the pools, posed with other traveler’s in their uploaded photos, I’d price compared between booking websites, because who doesn’t like a bit of couponing? Bangkok led to Ao Nang, which led to Railay Beach, and yes, occasionally I had to leave my sanctuary for the mean shores of Kayak or websites with incomprehensible train timetables, but I always quickly found myself returning to the comforting prow of the easy to navigate cyber ship that is Tripadvisor.

In the end, I’d poured a full and relaxing week of free time into designing the perfect trip for our first real vacation. I’d worked it all out, priced it, had every link and tab saved. All that was left was to make the purchases and see if reality could live up to the Tripadvisor-constructed myth in my mind. A part of me doubted it possibly could. But then something else happened. My job ended suddenly weeks earlier than I’d anticipated and the trip had to be put on hold for money reasons. The thing is, despite being quite sad, I’d kind of taken that trip already. And it was beautiful.

We never ended up going to Thailand. Months later, and in a better financial position, we took a shorter, slightly less insanely involved trip to Mexico, also heavily aided by my new online friend. It was magical and formative, better in ways than even Tripadvisor could’ve simulated, and probably the topic for another time. However, despite that wonderful IRL trip, I’ll never forget my excursion to the Thailand of my mind. Brought to me, by Tripadvisor.