Dear Yanni...Travel Insurance — Yay or Nay?

Dear Yanni...Travel Insurance — Yay or Nay?

This week Yanni dives into the best practices for travel insurance and same day round-trip business travel.

Dear Yanni,

I had bad travel luck on my last trip, and it got me wondering: Should I become one of those people who gets travel insurance when they travel? I’ve heard it argued both ways, but I honestly can’t tell whether it’s a life-saver or a scam.

-Insurance Ignorant in Indianapolis

Short answer, most insurance isn’t going to do what you expect it to — like save you in a flight cancellation jam. We’ve all seen the “one more thing before you go” tactic on many airlines’ websites to get you to book a car or travelers’ insurance. The reason it’s there is that you’re probably eager to finish the transaction and less eager to read 14 single spaced pages of legalese on what the heck you’re buying for $24.99.

A lot of travel insurance is aimed at extreme catastrophes. If you don’t believe me, I invite you to read the fine print and the alarming definitions of those catastrophic qualifying events for reimbursement. If you’re after protections for logical stuff like lost bags, disruptions and delays you’re partly in and out of luck. 1- many of those events are already reimbursable by airlines (lost bags, staff/aircraft-related delays); 2- it doesn’t matter what insurance you have, no one’s sending Iditarod-trained sled-dogs to save you when everything shuts down due to a blizzard.

Chances are you may have coverages you don’t even know about. Check your credit cards’ benefits or call and ask about the coverage you already have for the nuisances of lost baggage or extreme disruptions. You may be surprised to find that you already have some tools in your wallet. Just be sure to book the travel you want covered on the card with the coverage. And while it may be a pain to file to be reimbursed from an airline, there are consumer protections. Do keep in mind that each airline has their own process- some giving automatic credits, while others make you jump through hoops. Also, for travel within Europe/on a European carrier there all sorts of protections from the EC 261 regulation- it covers passengers for delays with up to nearly $700 for a disruption, which can more than pay for the extra croissants and morning coffee while you waited- “make it a double, please.”


Dear Yanni,

A lot of my business travel is for a single meeting or client visit. Historically, I’ve spent the night when I make these trips, but with a new child, I’m starting to think I should try to make it a one-day trip. Is this too risky? Am I just asking to end up scrambling to find a last-minute hotel when my flight inevitably gets delayed or cancelled?

-One-day Wonder in Washington

You wake up, stroll into the airport, fly to a meeting and get back home in time for Taco Tuesday. The. Dream. Is it the impossible dream? No. Is it the oft-implausible one? Yes. Same-day round-trip travel is risky business if not done right. If done well, it can be a savings on time, overnight stays and can be good for traveler efficiency and/or morale.

Be more realistic, less optimistic. Can one, in theory, fly from White Plains to Fort Lauderdale for a meeting in Miami at 1pm and turn back around to a New York area airport that same night for a nightcap in the city? Sure. But then fog happens at HPN airport, and then you’re circling over the Everglades because flights are held due to a passing thunderstorm, then there’s a backlog of people waiting at the car rental facility in FLL, then a lane is closed on I-95, then… well you get the point. We all love to imagine the world running efficiently; ever notice how people will reference where they live from a city as if there’s never traffic? “I’m just 20 minutes from the city”... on a Wednesday at 2am you are, sure. Well, somehow the same unicorn visualization of a world without other people in it is often how folks approach same day travel. Don’t be that person. Ask yourself, is it possible by schedule? If yes, next ask yourself if there were a delay of 90 minutes somewhere could this be a problem? If yes, then proceed only if able to accept being late to client meetings or stuck somewhere overnight, and don’t throw a fit when that happens.

When you book travel matters. We are often incentivized to book flights as far in advance as possible to save the most on a flight. However, if travel can be flexible by a day or two, then it may behoove one to wait until as close to the date as possible and to keep an eye on the disruptors for that week like weather, major events (marathons, conventions etc) and choose accordingly. It may cost more, but more reliability is worth the cost of entry. Time of day for your outbound flight also matters. While first-thing-in-morning, why-am-I-up-this-early [not-even-birds-are-awake-yet] flights can be rough for many of us, the aircraft for many of these flights are often there and waiting for the first flight as most airlines build overnight buffers to atone for cumulative delays from the day prior, which means that first-out flights can benefit from that schedule.

Consider alternatives. Some travel corridors have many options. Think parts of Europe, Asia and the Northeast. The number of travelers in a place like New York that will fly to Boston or Washington, D.C. after getting burned before by flight delays from simple weather events like clouds (literally clouds and light drizzle will ground short-haul flights for hours) is baffling. Unless you find your innermost zen in a crowded airport or stranded on a tarmac in a 47 aircraft-long taxi line, why not consider a train or even renting a car and driving? In particular, when planning in advance during the most disruptive weather seasons, and given that rail travel is more flexible in terms of rebooking or cancelling, consider this as a reasonable option. You know how people say “planes, trains and automobiles”- don’t forget that the latter two are viable alternatives.


About the Author: Yanni Poulakos
Yanni has had the travel bug from a young age. From traveling to over 50 countries and stints spent living in Asia, South America, Europe and the Caribbean, his insights into hacking personal and business travel are grounded in first-hand experience. As a former road warrior, he once covered every province in Italy in 6 weeks by car, served as a travel manager for dozens of colleagues across the US and Europe while leading a fundraising team, and customized exclusive travel experiences for a smattering of politicians and celebrities. No matter whether at home or on the road, Yanni stringently adheres to his approaches to nutrition and self-care, with a fervent commitment to help others do the same.