The 21-Point Scouting Trip Checklist (What To Test Before You Relocate)
How to visit as a future resident
A reader emailed me in December.
He and his wife are planning a scouting trip to their target destination.
They want to figure out if their place is “the place” to retire to.
Love to read this, since this is exactly the right way to go about it.
You can only read so many articles about a place, until you need to go and see it for yourself.
But here is what usually happens.
People fly in, stay somewhere cute in the touristy part of town, eat well, walk around, and come home thinking they found paradise.
Then they actually move.
And six months later everything is different:
The pharmacy does not carry their medication.
The internet dies in the middle of an important call.
The bank needs documents they never thought to bring.
The neighborhood outside of the tourist area has noisy construction sites.
Going for a 10-day vacation in the tourist part of Rome, visiting the Colosseum and eating pizza every evening is not “research”.
You are not there to enjoy yourself (well, of course also that).
But mostly you are there to test whether your actual boring daily life works in this place.
The checklist I created can be used for your scouting trip, to make sure you’re not missing anything.
Before You Go
Before we get into what to do during the trip, a few things to sort out before you leave.
Trip length
Go for three weeks minimum. Six weeks if you are able to.
Anything less and you are still in vacation mode, and vacation mode is not “living mode”.
Around week two or three, vacation mode wears off. That is when you start seeing the place a little clearer.
Alert your bank
Call them before you fly, or your card gets frozen on day two when “suspicious activity” shows up in a country you have never been to.
Annoying problem, easy to prevent.
Medications
Bring everything in the original packaging.
Bring prescriptions and a medical certificate from your doctor explaining what you take and why. Some countries ask questions at customs (most do not).
But the one time they do, you want the paperwork.
Passport validity
Check that you have at least six months left before expiration.
Some countries will not let you in otherwise. Takes two minutes to check, saves a disaster at the gate.
The boring prep is what avoids annoying and avoidable disruptions.
If you are between 50-75 and want to emigrate within the next 0-5 years, and don’t want to navigate healthcare, banking, visas, taxes and country selection by yourself, reply to this mail with “Retire”.
You’ll get a private invite to the “Retire Abroad Priority List” with some of my best tactics for retiring abroad.
The Checklist
21 things to test, grouped into seven categories:
Healthcare
Daily Life
Housing
Money
Social
Visa and Admin
Mindset
Print this out and take it with you. At the end of this article, you can download the full checklist as a PDF, with extra pages to take notes along the way.


