Should I Cancel My Summer Vacation or Fall Trip?

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By Megan Spurrell, Condé Nast Traveler

It's been months since the new COVID-19 reality, and the question of when we'll travel again remains nebulous.

Many travelers are wondering: Should I cancel my summer vacation or fall trip? Or should I postpone? When do I make the final call? When you choose to rethink your travel plans can impact the amount of money you're able to recoup and the flexibility you'll get in rebooking. We spoke to three industry experts about what to consider—and when to start the process—when it comes to postponing and rebooking your travel plans over the next six months. Here's what they said.

Create your own timeline and deadlines for postponing

There's no one-size-fits-all answer on how far out to start postponing your travel plans: it completely depends on who you booked with and what their terms and cancellation policies look like. Do your due diligence now—including reading any fine print—and understand when you need to make a decision by.

"Discuss the repercussions of canceling," says Jack Ezon, a global travel specialist and founder of Embark Beyond. "Are there cancellation policies you need to think about? Is this a time-sensitive decision?" Figure out what current cancellation policies look like for everything you booked: your flights, your accommodations, your cruise, any tours or experiences. Know when those deadlines are approaching, and figure out when you need to start taking action.

If that time is months away, force yourself to cool your jets—and wait it out.

"Generally speaking, it’s better to be canceled on than for you to cancel on a discretionary basis," says Gary Leff, the author of ViewFromtheWing.com and an expert in points and miles. "If you’re canceling voluntary, not because travel is being canceled on you, your position is less strong for a refund—in terms of getting refunds from providers, in terms of filing claims with insurance companies, and certainly with airfare." Leff says this holds especially true with airline reservations, which you can cancel up until the scheduled departure time. "I would not be addressing your flights weeks in advance."

For trips into early summer, Ezon's team is telling clients that they should anticipate postponing their travel. "For anything from mid-June and beyond, we’re encouraging people to wait and see," he says. "That June date is fluid, but that’s what it looks like today. It's important to keep revisiting that, and remember things are changing at lightning speed." That all said, Ezon's team still has plenty on the books for July and August. "As long as there’s no [financial] penalty to wait, and you're not being asked to place additional deposits or put more money on the line, there’s no reason to cancel [right now]."

Reach out to those you booked with before you need to postpone

Though your timeline should be based on cancellation policies, know that none of those rules are written in stone—especially in an unprecedented situation like this one.

"Have a conversation with the person you're working with," says Leff. "Don't just read the agreements and assume those are the options you're currently facing. The person on the other end doesn’t want to lose your business, so they might give you greater flexibility. They’re also going to want your business when things return to usual."

If you booked through a travel specialist or third party, let them go to bat for you. "Having a transparent discussion navigated by a travel advisor can be extremely helpful and mutually beneficial," says Ezon. Not only do these travel experts have the experience—and time—to talk these things through with vendors, but their collective bargaining power can be useful to travelers and travel companies.

If you can afford to, consider postponing your trip instead of canceling altogether. You might be able to negotiate something more favorable for when you do take the trip later on, and, you'll be supporting travel providers in a time of need. "In general, our philosophy is we're all in this together," says Ezon. "We're an advocate for our travelers first and foremost, but we also need our vendors and suppliers to stay in business, not just for moral reasons, but to sustain this business. If there are no small tour operators and beautiful boutiques [left], our clients won’t get to experience those things when this is all over."

Proceed cautiously on new bookings

Some travelers are still making summer and fall plans, even though they aren't sure they'll be able to see them through. For some, scheduled events that haven't been called off, like summer or fall weddings, are placing guests in limbo. There's also the appeal of cheaper fares and flexible cancellation policies.

For opportunists eyeing low fares, Leff encourages travelers to wait it out. "There isn’t an imperative to jump on good fares now," says Leff. "As flying comes back, it won’t be like flipping a switch and the planes are full. I wouldn't feel a need to jump on a good price today, because there will be good, possibly great, fares later."

"The best thing anyone can do right now is to understand what their options are," says Megan Moncrief, chief marketing officer at travel insurance comparison site Squaremouth. "The industry as a whole is doing what they can, providing refunds, vouchers, and credits at an unprecedented rate. As a consumer, I wouldn’t feel confident traveling this summer, though I would feel comfortable booking travel in the fall—but I’d want to know my options."

Ezon agrees that any new travel booked should factor potential risk from the get-go, and what it will look like should you need to cancel. "What is the viability of getting your money back?" says Ezon. "And how are you paying? That's very important when it comes to tour companies especially. If you pay by wire or check, you have very little protection, especially if that vendor goes bankrupt or closes shop. If you pay by credit card, cards will usually protect you, depending on the card. If you have travel insurance, that can also protect you."

Know what insurance will cover

Though most travel insurance plans do not cover pandemics, there are ways to navigate existing plans to meet your current needs. "There is still coverage if you contract the virus, or if you’re quarantined, and there’s also coverage for the financial fallout from this, say employment layoffs, or financial default of the provider," says Moncrief. On sites like Squaremouth, customers should make sure those scenarios are included in any plan being purchased right now.

Of course, you can also spend more on a cancel-for-any-reason (CFAR) plan to protect yourself as thoroughly as possible. "CFAR is the still your best option, especially if you just don't feel safe or don't want to go [when the time comes]." It works exactly like it sounds—you can cancel for any reason, no explanation needed. You won't get 100 percent of your money back, and you have to follow strict rules in how you book—and you must purchase the insurance within a small window of booking the trip itself. Read more about this in our cancel-for-any-reason insurance explainer.

Though waiting to make the call on upcoming travel plans can be tough, Leff says the emotional upside can be worth it, too. "Keep your trips as something to look forward to through this, until you have information to make a decision," he says. "Keeping something on the books gives you something concrete to hang on to, at least from a personal standpoint. You can look forward to when the world is better, healing."