A serious guide to planning a relaxing vacation, seriously

First of all, how was your pandemic? Spirit-crushing? Zero stars? A little cloudy? Well, at least we can finally entertain the idea of a vacation outside of our home, yard, and if you were a risk-taker, the nearby park. This hasn’t been a reality for more than a year and if you’re not in need of a relaxing vacation right now, then you’re in an infinitesimal minority.

Judging by the raucous scene in downtown Minneapolis the past few weekends, a lot of people aren’t thinking relaxing vacation as much as they’re thinking “PAR-TAY, motherf*cker!” But if you just turned 51 like me, and have been behaving like a 51-year-old for at least a decade, your first post-COVID vacation ambitions may be more subdued. A truly relaxing vacation. Not the kind where you maybe relax a little after breakfast and then go do an exhausting number of activities in the afternoon. I’m talking about full-time, full-body, uninterrupted relaxing.

A relaxing vacation should involve vibrantly colored drinks

I have been a do-nothing vacation evangelist for a long time now. I’m trying to save the world here – or at least a tiny part of your sanity, so heed these words.

How to plan a relaxing vacation

First, forget everything you know, or think you know, or saw in that one travel influencer’s YouTube video. That was probably sponsored content anyway, based on a vacation where the tourism board paid for everything.

You must clear your mind, grasshopper. We need to disconnect you from the trend of vacation over-planning. Remember when a relaxing vacation used to be the default and only lunatics and sociopaths planned hectic and even productive vacations?

Activities that cause brain cells to light up can be fun, no question, but, again, this past year has been brutal. Give your squishy, think-y blob a break. Don’t over-correct and submit to the kind of vacation where you’re more exhausted after the vacation than before you left.

This is your first proper, post-COVID vacation. You want to nail it. Using my vast travel-panning wisdom, I’ve compiled the following tips to get you out of a bungee-jumping harness and into a supine position, perhaps with a little single-celled reading on your lap.

And remember the most important aspect of taking a vacation; Making your friends and coworkers wretchedly jealous.

The destination is key

You can’t relax at a destination with alluring activities and attractions. Ideally, you want to be hours away from the nearest thing that makes you think “I’d like to see that.”

Pick a destination that’s lovely and special, but boring as hell. My first attempt at a relaxing vacation was a wild success. I went to the pleasingly lackluster environs of Granada and San Juan del Sur in Nicaragua, where I slept, sat still, napped, ate wondrous food, drank vibrantly-colored cocktails (see above) and then slept again. If my hotel hadn’t been on a hill, I don’t think my heart rate would have reached 80 all week.

If at any time during the trip, you feel the urge to walk more than 200 yards all at once, you’ve chosen poorly.

If the destination has more than two guidebook pages devoted to it, you’ve chosen poorly.

If you ever say to yourself “Huh, I wonder what that thing is over there?,” you’ve chosen poorly.

Leave your tech behind

I know, this part may be a little painful. Tech can be so fun. Laptops in particular are indisputably wonderful little entertainment boxes, but most of us also have work-related or work-accessible content on our laptops and that is relaxing vacation sacrilege.

Bring an ebook reader, a phone, even a smartphone to if you absolutely have to stay in touch, but any device with a trace of work content must be left behind.

Finally, people especially prone to Twitter and Instagram distraction should be strip-searched for devices by a professional before leaving home.

Pack for the trip you want

In other words, don’t bring fancy clothes. If you bring fancy clothes, you’ll want to wear the fancy clothes, which means you’ll want to go somewhere fancy, which means a lot of fancy prep time and fancy behavior and fancy etiquette and this is already sounding like far too much effort.

Going out for a decent meal while on a relaxing vacation should not entail any preparation more rigorous than walking the dog. Here’s a good benchmark: Any restaurant that won’t seat you while wearing a tasteful Simpsons t-shirt is probably too much work.

Also, no hiking shoes. Hiking is to a relaxing vacation as whiskey and Red Bulls are to a serene, civilized evening in Bangkok.

Packing and destination criteria speed round

Your relaxing vacation destination should have, or you should bring along, at least four of the following components/paraphernalia:

  • Any place with swimsuit weather
  • Hammocks
  • Body of water (pool, ocean, lake)
  • Lots and lots of towels
  • Reasonable food within 200 yards of your bed
  • Cocktails in primary colors within 100 yards of your bed
  • A vista that’s better than most TV shows
  • A large variety of reading material in the following genres: humor, adventure, sci-fi, teenage wizards, biographies of people who didn’t die in an especially tragic way, superheroes being awesome, and warlords that were so crazy they named a vampire after him

Relaxing vacation no-nos

Whenever anyone utters the following words/phrases, they need to put a dollar into their companion’s cocktail fund:

  • ‘What time is it?’
  • ‘Overslept’
  • ‘Pants’
  • ‘Should’
  • ‘Hard Rock Café’
  • ‘Work’
  • ‘Work out’
  • ‘Too much’
  • ‘Too late’
  • ‘Too early for [insert alcoholic beverage]’
  • ‘Too fattening’
  • ‘Too drunk’
  • ‘Too naked’
  • ‘The economy’

Do you have any do-nothing vacation tips to add?

If you enjoyed this serious guide on how to plan a relaxing vacation, seriously, you may also enjoy my serious guide to setting up a travel blog, seriously.