The Daily Drop team recently got back from a company retreat in Costa Rica. Surfing, sun, good food, and⌠yes, a fair amount of travel chaos. Planning travel is a lot like planning a wedding⌠no matter how prepared you are, thereâs always something that doesnât go to plan.
Here's the thing about working at a travel publication: you start to believe the chaos that happens to other people won't happen to you. You know the tricks. You've logged the miles. You have the apps, the lounge access, and the backup plans.
Costa Rica said: hold my guaro.
Hereâs the story of what happens when things donât go to plan on the road - and how to deal.
Getting Bumped Is Not the End of the Story
Our colleague Daniel had his domestic flight within Costa Rica quietly reassigned on him. No notification, no explanation, just a new departure time that would land him two hours late and unravel the rest of his day. His original ticket was non-refundable and non-changeable, which is travel-speak for: "officially, youâre screwed."
Quick pause for anyone new to this: when an airline bumps you to a different flight (meaning they change your flight without asking), your options depend on the type of ticket you bought and the airline's policies. Cheap fares often come with restrictions that make it hard to change things. But "hard" and "impossible" are not the same thing.
Daniel asked if there was anything they could do, and a few WhatsApp messages with a manager later, he had a new ticket in hand. An actual physical plastic chit that he handed directly to the pilot before boarding a single-engine prop plane.
The real lesson here isn't just about asking nicely (though, yes, definitely always do that). It's about the time buffer Daniel had built in.
What travel experience actually buys you is the instinct to ask, and the habit of leaving yourself room to breathe.
When the Airport Itself Is the Surprise
A few others had a completely different kind of adventure on the ground at SJO (San JosĂŠ's Juan SantamarĂa International Airport, the main international airport in Costa Rica).
After landing and clearing customs, Emily, Greg, and Brendan followed the signs for connecting flights to their domestic leg. And then the signs just stopped. No airline counters. No clear path back to a gate. They wandered outside, asked for directions, and were pointed down the street, as in the actual street outside the building, toward a domestic terminal that had no physical connection to the international one whatsoever.
This was a group of people who have collectively been to more airports than most people have been to the gym.
They got turned around at SJO. It happens to the best of us.
Emily's silver lining from that same trip home: she had a two-hour layover in Atlanta (Hartsfield-Jackson Atlanta International Airport, the world's busiest airport), and her Global Entry membership got her through customs in under five minutes while the non-Global Entry line stretched toward the horizon. Global Entry is a U.S. government program that lets pre-approved travelers skip the regular customs line when returning from international travel. Emily paid $0 for hers because it's a perk reimbursed through her travel credit card.
She also spent that layover at the Amex Centurion Lounge in Atlanta as a guest of her colleague Daniel, who holds the American Express Platinum CardÂŽ. Emily's verdict on the $50 guest fee: absolutely worth it for the dinner, the drinks, the Wi-Fi, and the company.
Zoe's Return Trip Deserves Its Own Category
Our colleague Zoe's journey home was less "travel chaos" and more "travel chaos speed run." Buckle up.
She was booked on a four-flight itinerary on May 15th: ACO (TobĂas BolaĂąos International Airport, a small domestic airport in Costa Rica) to SJO (San JosĂŠ) to PTY (Tocumen International Airport in Panama City, Panama) to KIN (Norman Manley International Airport in Kingston, Jamaica).
Zoeâs first flight left 35 minutes early. She arrived just after it took off. She described seeing the dust still rising off the runway.
Now, a quick note for anyone who hasn't dealt with small regional airports: at smaller airports in places like Costa Rica, not every flight listed on the schedule actually operates every day. The next direct flight Zoe could realistically catch wasn't until 9:30 pm that evening, and it was on a different airline entirely.
This mattered because Zoe had a connection in San JosĂŠ she absolutely could not miss: an 8:47 am flight to Panama City. Missing that first leg meant potentially missing everything after it.
That wasn't going to work. Zoe needed to be in Jamaica by Friday evening for her aunt's 60th birthday party on Saturday.
So, she made a call. She'd already booked a backup: a separate flight from San JosĂŠ to MIA (Miami International Airport) around noon, arriving just after 5 pm, followed by a second flight from Miami to Kingston just after 6 pm. American Airlines wouldn't sell those two flights as a connecting pair because the layover was less than an hour, which is shorter than their minimum connection time. But Zoe had done the math herself: she had no checked bags (just a backpack), and she had Global Entry, which means no waiting in the customs line in Miami.
She cancelled the Copa itinerary, got a partial refund, caught the 9:30 am domestic flight from ACO to SJO, then the noon flight to Miami. The Miami flight landed 20 to 30 minutes early. She sprinted through immigration, cleared customs in minutes thanks to Global Entry, and made it to her Kingston gate right as they were boarding.
She made it to the party.
So What's the Takeaway?
The people on this team have been to a lot of airports. They've navigated a lot of complicated itineraries. And Costa Rica still managed to humble them in three completely different ways in the span of about 48 hours.
If there's a thread running through all three of these stories, it's this: the trips that go sideways don't go sideways because experienced travelers donât pay attention. They go sideways because travel is genuinely unpredictable, and the difference between a disaster and a good story is usually preparation before the trip.
Build in buffer time. Know your options before you need them. Travel light when your connections are tight. And if someone changes your flight without asking, it is always worth asking what they can do about it. Know what your credit card covers if your flight gets cancelled. This article covers how to rebook yourself, just in case.
A Note About Where We Were
The retreat that sent us all scrambling home through Central America was hosted by Pura Vida Adventures, a surf retreat operation on the coast of Costa Rica. If you've ever thought about combining a team trip (or a personal trip) with a real surf experience, they're worth looking at. Tierza and her team took excellent care of our crew. Greg even went home with the Tower of Stoke Salsa Lizano Award, which is exactly as chaotic and wonderful as it sounds.
