In August I did the unthinkable - I went on vacation to an all-inclusive resort. It's unthinkable for someone with so little self-confidence to think they deserved luxury, and so simple-minded they'd be happy with a vacation to a vineyard and a few bookstores.

Yet it happened, and like all things weird in my life, I must write about it. Many realizations hit me in this trip, some more interesting than others. The smaller ones I don't need to go into detail, like:

  1. Pool bars aren't worth it.
  2. Free room service is absolutely worth it.
  3. Ask about towel cards.
  4. Don't get excited about magician performances. 70% of the act is cheap string stricks.

Those aside, here are the three most useful ones I'd recommend for others considering a luxury trip.

1. Pure Luxury Is Impossible #

Lying outside in the sun, even with a canopy bed, is relaxing for about two hours. It's kinda nice for another hour. It gets boring for the next several dozen. Good books can delay this effect a little, but not for long.

When good reading can't make the situation better, that's when I know things are screwed.

This was just one of a large pile of first-world problems. Those, paired with a big sense of entitlement after expecting "all-inclusive luxury," made them hit my annoyance extra hard:

Luxury is just another form of stress, which some people may or may not prefer.

All this made typical "high-class" luxury lose its appeal, and at times feel more stressful than everyday life. Ironically enough, the most relaxing things were the small, silly things unrelated to the resort. Like playing card games we took too seriously with sex-position cards. Those aren't luxury-resort related, but are some of my fondest vacation memories.

I don't think true luxury exists, since even the "high class treatment" caused us stress. True luxury is finding the things where the stress doesn't bother me as much - like a peaceful cabin trip. There's the stress of making our own meals, keeping warm at night, and entertaining ourselves in solitude, but those kinds of things don't feel like work to me. It's satisfying for me and my partner to take care of ourselves and enjoy our solitude. The point of my vacations is recovering from stress. The trick is finding the stress that's enjoyable.

2. Travel May Not be Worth It #

Even when just going halfway across the country, air travel is a huge pain for me. Getting to the airport early, dealing with security, cramped flights, jetlag, and peanuts that slowly brainwash people for the Illuminati conspiracy. Dealing with all these takes too much time, energy, and anti-venoms to be worth it.

If a vacation is about lowering stress over anything else, I advise keep it close to home. Half my vacation time was spent at the resort and the other half was spent at home. In the second half I was catching up on chores, video games, side projects, and trying new food around New Haven. It was relaxation without the crowded airport terminals. That's why I'm aiming, for my next vacation, to go somewhere by car instead of plane. Just to see how much better keeping it local could be.

A common argument I hear against staying local is finding different people and cultures. I'd say that's great as long as I meet two conditions:

  1. I actually want to experience more of this other culture. I'd love to see more Japanese and Italian culture in person someday. Culture from places like Russia or Saudi Arabia? Intriguing in a sense, but probably not worth it.
  2. I'm getting the real culture, not some prepackaged and sanitized version often included with a resort. I'd be better off finding a random flight somewhere, checking into the closest hostel, and wandering into a new city each day. Which would be lots of fun, but sounds better to me as a day trip instead of a week-long vacation.

My point is that long-distance vacations aren't universally better. Unless I have a good, specific reason for going someone far away, sticking closer to home is better for low stress.

3. Choose Your Company Wisely #

Despite the many issues that popped up on my vacation, I still enjoyed it. It's not just because I drank so much I sworn off alcohol for a month. It was because I made the trip with the right person, which can salvage almost any trip. Someone can go through the ups and downs with you and share a laugh about them later.

For example, when the number of mistakes and miscommunications reached a boiling point, I had someone else to complain to the staff with. They did all the talking, were the main reason our stay got upgraded and got better, and left me feeling kind of in awe. But the larger point is that turbulence brought us closer together after.

Only the most well-established relationships won't shift after a major vacation together.

So while the location may seem like the most important decision, it's actually who you're going with (or not going with). In all honesty, I think it'd be better to travel alone that with the wrong person. All that trip would do is make things worse without any guarantee they'd split up afterwards. I got very lucky it was the total opposite. So for both good or bad relationships, big vacations together will shake things up. Be ready for the tremors regardless.

Conclusion #

My biggest takeaway from this vacation was an obvious one in hindsight, that luxury vacations aren't automatically better. The extravagent details and "oohs and aahs" from the people I told about it did a good job fooling me up until we arrived. By the time I left, I know it'd be a while until I stay at a place with "all-inclusive" in the title.

Just choose the vacation that'll make you happiest. Even if it's visiting every Presidential museum and chocolate factory within 150 miles of your home.

Spoiler alert!