What is transition day like on Remote Year?

This isn’t a topic I have seen anyone else write about, so I thought it might be interesting for you to get some insight into what our travel days are like. Each month, we all transition as a group to the next city we’ll be spending a month in. As part of my program fees, Remote Year plans out all of the logistics of getting from one city to another, and they book it for us. This includes booking our flights and arranging for transportation to/from the airport. This is a blessing for some and a curse for others (I’ll let you guess which camp I fall into :)).

And I’ll preface this by saying that I literally picked my flight to Lima based on the plane type (i.e. the 737 MAX — before it had all of those issues!) – so I am not your average laid back, easy going traveler. I have an opinion/preference on all sorts of things the average traveler likely doesn’t, and I expected going into Remote Year that the travel days would probably be one of the tougher things for me to adjust to.


About a week before transition day, you’ll receive an email with all of the transition information for your move to your next country. This includes your address and roommates for the next city, as well as the final flight details and transition day schedule.

Checking out from your apartment / pickup

On transition day (typically a Saturday), you are typically picked up fairly early in the morning (around 8-10am), regardless of what time your flight is. The city team needs you out of your apartment so that they can clean and check the condition of all of the apartments before the next RY group arrives (often the same evening). Remote Year coordinates and pays for the transportation from your apartment to the airport.

In Lima, we had busses pick us up around 8:30 am, and we were all taken to an Irish bar for the day, where we had brunch, played trivia, and hung out until the busses came back to take us to the airport at 2 pm.

Luggage storage on the back patio at Molly’s
Brunch at Molly’s while we wait for busses to the airport

In Santiago, we were picked up from our apartments around 10:30 am and driven straight to the airport for our 2pm flight to Medellin.

Airport check in always feels a little crazy – I am used to traveling alone, so rolling in with 35 of my closest friends means that even if there wasn’t much of a line before we arrived, there will be a long one when we all show up at the same time.


For Lima – Santiago (a 4 hour flight), we flew Sky Airlines. Sky Airlines is a low-cost airline based in Santiago, which I can best describe as pure hell. Haha. Kidding, but not really. They are essentially the Spirit Airlines of South America, so you get what you pay for. In this case, the seats were extremely cramped, and there was no food or beverage service (even water was not provided without cost).

For Santiago – Medellin (a 7 hour flight with a layover in Bogota), we flew Avianca. Avianca is the national carrier for Colombia and is part of the Star Alliance. While nothing fancy, this flight was on par with any other international economy flight I’ve been on. Remote Year did alright with this one.

Remote Year has you fill out a bunch of surveys before you embark on your year long journey, one of which includes things like whether you prefer a window or an aisle seat, what your dietary requirements are, or whether you’d be interested in paying for upgrades on flights. While it’s a nice thought, I don’t see those preferences actually being taken into account, at least not on this inter-continent flights. I’d really prefer that they gave me my own booking, so that I could easily log in and choose my seat, bid on upgrades, etc. Instead, the entire tramily will be on one reservation number, and many airlines will give you a hard time trying to select your seats on a reservation you didn’t book.

Arrival at destination

When you arrive, after picking up your luggage and going through customs and immigration, the local Remote Year city team will be waiting for you. They will typically have snacks and water for you, and they organize the busses that take you to your new home. This is often when you receive your sim card for the month, if you have opted to pay for this service.

In Santiago, this pick-up felt a little chaotic. There wasn’t any info provided to us about where to meet the team, and several of us ended up standing outside on the curb our own for a while, while we tried to find the group. We waited a while for the busses, and then had to walk the equivalent of a couple of blocks (with our luggage) to reach the busses.

In Colombia, the city team was waiting for us at baggage claim, had plenty of snacks, and had assigned us busses ahead of time, which were waiting outside the doors when we arrived. Smooth sailing.

Apartment check in

As we’re all spread out in multiple apartments (and multiple buildings) throughout the city, the busses will each likely make several stops to drop people off. In Santiago, we arrived to our apartment around 1:15 am. We were dropped off and walked to the lobby of our apartment building, where we were handed keys and directed to the appropriate building/elevator. Waiting in the apartments is always a piece of paper with the wifi info and any other pertinent apartment information.

In Medellin, we arrived around 12:15 am. We were walked to our apartment door, and each of us tested our key to make sure we could get into the apartment without any issues. The city team also had us log into the wifi before she left to ensure that was also working. This was evidence of a seasoned city team – both of them have been in their positions for over a year, and for one of them, we were here 22nd Remote Year group.


Transition days are often long days, regardless of what time your flight is, or how long of a flight it is. The unglamorous side of moving every month means that you spend a full day (or more) each month traveling to the next location, and it’s not always an airline or a schedule you would have chosen for yourself. There is a nice benefit to not having to sort out your own transportation when you arrive, and of course, being greeted with snacks and water is a nice welcome as well.