Why Going on Vacation Before Moving to a New City is a Gamechanger

From Vacation to Staycation

To be completely transparent, this strategy I would say beneficial for people who are still debating what city to live in next. I wouldn’t consider it is for those who have the U-Haul and the kids packed in a Toyota, so swipe up if that’s you.

Photo by Mantas Hesthaven on Unsplash

Okay, now that I have you guys here, let me break down how I came to this conclusion.

I just moved to New York City. I plan on at least staying for six months, and that time span depends on if I have a “New York Minute,” and all that I’ve ever wanted ends up just falling on my lap.

However, I had a vacation planned for New York a month before moving there was even a conception.

I immediately thought to myself how seamless this would be, followed by how profoundly stress I became of the whole situation. Packing for vacation and packing to move in did not sound ideal.


It ended up working out. Even better, if there is some unexpected weather, then you have all your other bags as a plan b. Would you look at that!

I had four vacation days (all of which were jammed packed, we ended up walking over 35 miles which I would not recommend). My family and I had some moments where they did help me buy things for the sake of having extra hands on the train, but otherwise, it was a full-on vacation. As stressed out as I could’ve been for the whole trip, I wasn’t, not even until the last second, and here is why:

We spend so much time working. You know this. We move cities for work, we travel for work, we are digital nomads, etc.

But how many times do you hear someone say, “You know I’ve been here five years and never went to that bar,” or “Even though I’m living in Japan, I mostly never leave the house because of work.”

You say to yourself, “I have time,” or “I’ll do it next week.”

But the next week comes, and you don’t do it.

You spend so much time sticking to the objective that you lose out on what the place has to offer. And suddenly you left, and you never know when you’ll go back there again.

The vacation is a moment to take some days off and do it all.

  • Explore the sights
  • Be a tourist
  • Eat until your stomach hurts
  • Dive headfirst into the space you are living in before you head off to work on Monday.

Don’t keep brushing off places you want to go to.

I discovered in those four days:

  • Familiarizing myself with nearly all of Manhattan (and a touch of Brooklyn)
  • Restaurants I already know to go to
  • Places to further explore because I had the chance to go there before

And that brings me so much ease as I venture out on my own now.

Tip: Find/make a friend who is a local in the area

Having my sister take a staycation here was a blessing in disguise because she knows where to go and where to eat and what to do. They can provide you their view of the city or you both can have a tourist moment and do activities neither have done before.

All of this is to say that at the end of your time there, even if you end up spending your time at home or work (at home), you can say that at least you did something.

I still hate the fact that I lived in East Bay and never went to Alcatraz.

I was not about to make the same mistake again.

So, next time you think about moving somewhere, having some days ahead to enjoy where you’re heading to next. Just make sure the Airbnb/Hotel can accommodate an obscene amount of suitcases.

A 20-something who stutters and trying to figure out how to deal with it on top of adulting shenanigans and discovery