Coming out of the winter slumber, it’s already time to start thinking about summer vacation. We’re going to Greece; but, that’s not vacationing. That’s an obligation to see family. We just don’t know where to vacation this year?!?!? So far, Slovenia tops our list. It seems to me that vacationing has become a lost art. Tiktok and instagram are partly to blame for ruining vacations even before they begin by setting unreasonable expectations. The places you see on instagram are carefully curated, edited, and highlighted for likes. Reality is secondary.
Inundated with top ten lists, the best places to go when you’re in <insert city>, “secret” byways, “must dos”, and you become anxious about how your plans stack up. This is why vacationing has become a lost art. In this brave new AI-powered digital world, self-discovery, connection to the local culture, disconnection from the norm, authenticity, etc. are difficult to achieve when you’re competing with people looking for the same things in the same limited spaces. It all turns into one big shit show. Let’s not forget the pickpockets you need to avoid (still suffering ptsd). In the end, vacationing can be a miserable experience if you let it. This could explain the allure of the staycation.
Vacationing
In my mind, vacationing is not traveling. Obviously, you travel to get to your chosen destination; but, unlike traveling, vacationing is a controlled experiment in a sterile environment. You commit to a destination with a few extracurricular activities planned for good measure. A hero shot of you repelling down a waterfall, feeding a monkey, holding the sunset ever so in the palm of your hand is mandatory. You Eat, Pray, Love your way to likes from your envious friends. The key to vacationing is having the whole trip figured out from A to Z and planned around multiple outfit changes. You get seated near other strangers mirroring your same goals and aspirations in awkward dining situations where it hurts to smile politely. The quicker the staff can get you from breakfast to lounging around the pool so you can live your best life, the better! #blessed
As a management consultant in Washington, DC, I traveled extensively for work; exclusively with an American Express platinum card and only stayed at the Marriott. Following the lead of George Clooney’s character Ryan Bingham in the 2009 movie Up In The Air. I accumulated enough points to achieve lifetime Gold status with all its upgrades, welcome drinks, late checkouts, etc. Marriott revamped its loyalty program and Gold is now a “Fools Gold”. I only flew business class and used my TSA pre check to zip through security. Priority boarding three announcements ahead of Group 1 was the norm. In the points world, I was somebody to be respected. These days, I’m happily regulated to economy class with the common folk and couldn’t be happier.
Vacationing With Points
What did I do with all the points? I cashed them in and went on vacation to Hawaii. Without these points, I could never afford this vacation and was fortunate enough to vacation there on three different occasions. I also cashed in some points to fly my dad to Greece in business class where he was able to sip champagne (if he wanted) and stretch out for his transatlantic journey. He never got tired talking about that experience. I had to wait over ten years to enjoy that transatlantic luxury when I received a free upgrade flying to Zurich from Chicago.
In Hawaii, I hit up the breakfast buffet every morning with my trusty travel companion Rosalia. We became intimately acquainted with the waffle and omelette bars. Our daily breakfast creation and combinations were only limited by our imagination. Some days were more salty than sweet (nursing a hangover) and other days we opted for more sweet than salty (vacation calories don’t count). If you read the room at the breakfast buffet, you can totally spot all the points people reveling in their status. If you can’t see them, you can definitely smell them. The stench of entitlement follows them everywhere. The breakfast buffet at any resort is the most miserable place to be on vacation, followed by the hotel lobby bar. That can explain why we always had free drink vouchers remaining at checkout.
Shitty Points People
The worst people you will find in the points community are the entitled assholes that believe that they should get everything for free and treat the staff like shit. They also tip like shit. What is 15-20% of $0? It’s $0. As a rule, I always overtip to subsidize that asshole’s no tipping policy. Every morning I used to hit up the concierge lounge at the Marriott on Wolf Road near Albany, NY where everyone would assemble for a quick coffee and light breakfast before work. There was always one person that had a special request with asshole written all over it. I became quite friendly with the hostess and she did her best everyday to accommodate everyone. Without fail, there is always at least one asshole in every concierge lounge in every Marriott in every city I’ve been in the world. What are the odds?
The other asshole you find on a points paid vacation is at the hotel bar that never STFU. Avoid this person at all costs. They will tell you how to game the system and how to get yourself double and triple points. Their sole purpose in this life is to accumulate as many points as they can to pass through the gates of Walhalla as a double platinum member of the points community. They want to be in the top 1% of the obsessive compulsives. These people closely mirror coupon clippers that fill two or three shopping carts full of laundry detergent, cleaning supplies, diapers, and condoms only to pay $1.78 for over $1,000 worth of products. It’s quite silly when you think about it.
Separation Anxiety
The problem with vacations is the anxiety that comes from touristy areas seeking to separate you from your money. It’s hard to escape the thought of being objectified. All those smiles and over friendliness are there for the sole purpose of separating you from your money. The economics of it all are quite simple. For example, if you’re in Mexico, the Dominican Republic or Jamaica the price of goods sold to you is relatively cheaper than what you would find in the States. You’re on vacation so you do the conversion in your mind and talk yourself into buying something you don’t need because everything seems inexpensive.
When traveling in Europe, souvenir stores are everywhere selling t-shirts, magnets, and bottle openers. Stroll through the winding narrow streets of Plaka in Athens if you don’t believe me. You’ll find all the “This Is Sparta” and “Oedipus: The Original Motherfucker” t-shirts you can fit in your luggage. You’ll also find all the penis bottle openers in every color and size imaginable. Everything is always 50% off (only for you) and there’s room to negotiate if you pay in cash. You’ll find yourself overwhelmed by all the consumerism at your fingertips.
The Resort
My brother George is a serial resort vacationer. He’s always at some fancy resort in Mexico with his family. Ironically, they eat the same things at the resort that they eat back home. The kids get to junk out on food and the adults get to dive in to a few drinks and take it all in. This just isn’t my style. Once, we spent a week traveling around the Big Island and after staying in Spartan accommodations with limited amenities, we splurged for the final night at the Outrigger Kona Resort. From the first aloha when you walk in the door, you notice the difference in tone, ambience, linens, water pressure, service, andshut yourself off from the miserable points people lurking in the shadows. After being road weary from the past week, you can actually disconnect and get some well deserved rest.
Traveling
Traveling is a whole other beast or “genre” if you want to sound like a pretentious prick, because it requires accepting Murphy’s Law (“Anything that can go wrong will go wrong.” ) well before your journey begins. It requires you to live outside of your comfort zone. No amount of planning can prepare you for what the road ahead has in store. You are more likely to shit your pants in a foreign country from traveling than vacationing and this is the way I prefer it; but, vacationing done right is pretty awesome.
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