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There’s a lot of questions in the travel world right now. Will your reservation be canceled? Even if it isn’t…can you travel?

Should you?

A lot of the answers to these questions are changing in real-time. Right now, I have a trip to New Zealand and Fiji on the books for August, taking advantage of the recent Alaska Airlines/Fiji Airways deal a few weeks ago. For now, I haven’t canceled anything and am hoping for the world to be back to normal before August, but who knows.

What if you have a trip in the works, or that New Year’s Resolution trip to plan? If your travel plans are uncertain, I think they usually fall into two categories

  1. Book now (but make sure everything is refundable)
  2. or…wait

Should You Book Flights?

This one depends a lot on which airline you’re flying and what their cancellation policy is. If you’re booking through a travel agent or online travel agency be sure to confirm the policies with them. Personally, I like to lock in dates and book cheap flights for all my trips as far in advance as possible.

Right now, of course, everything is a bit up in the air. Check out our post on airline cancellation policies for COVID-19 here.

Southwest is the major exception to this rule. There’s no harm in booking your travel in advance with Southwest because they don’t have any change or cancellation fees! Now, if you pay for your flight with a credit card or Southwest gift cards, your refund will turn into a travel voucher. The travel voucher is only good for the named traveler and expires after one year. Better than nothing, but still a bit complicated. For ultimate flexibility, book your Southwest flight with points!

Almost always, travel reservations are more expensive when you want the ability to refund them. Go look at any airline, and compare the prices for refundable tickets against nonrefundable tickets. Still, if you’re worried you might need to cancel the trip, there’s definitely a case to be made. Just like an insurance policy, you’re paying a little extra, to make sure you have peace of mind. What about buying refundable tickets when you’re traveling for work?

Speaking of Travel Insurance..

Travel insurance is great when you’re dealing with uncertainty. Most high-tier credit cards come with travel insurance built-in, or you can buy a policy. You’ll have to choose what kind of policy you’d like. Travel insurance companies usually sell either an annual travel policy or shorter, per-trip policies. I have to assume most travelers only purchase the shorter term policies, but annual travel policies can be a great investment for frequent travelers.

No matter what kind of insurance you’re using, be sure to check the policy coverage. Travel insurance policies almost always cover your trip if you need to cancel or reschedule for the illness, death, or severe injury of you or a traveling companion, and often extend to family members as well. There’s often coverage for severe weather or terrorist/war activity as well.

Where to Stay?

Hotel reservations might be the easiest category here, since there are usually very good cancellation policies. In fact, I’ll usually book my hotel as soon as I have even an inkling of a trip idea in my head! I can almost always cancel my hotel booking as long as I do it a week in advance. Steer clear of any repaid rates – you’ll usually save a couple bucks, but you’ll forfeit the money if you have to cancel!

(SEE ALSO – What can you do when Marriott cancels an impending reservation?)

If you’re opting for AirBnB, VRBO, or some other booking engine, make sure to check the cancellation policy. I’m usually a big fan of AirBnB, so here are its cancellation policies. If you’re not sure about your upcoming trip, make sure you book a place with a Flexible Policy, giving you up to 14 days prior to the beginning of your stay to cancel with a full refund.

What About Restaurant and Activity Reservations?

This stuff I’d definitely hold off on booking. First, these are likely the easiest to make once your travel plans are confirmed. Most (but certainly not all) dinner reservations, tours, and activities can be booked once you arrive. Your hotel or credit card concierge can even help! Second, there’s a smaller chance of cancellation fees and deposits you’ll lose. Again, there are exceptions to the rule, but I’ve never been charged a deposit fee for dinner reservations. Unfortunately, deposits for tours and activities are sometimes non-refundable.

(SEE ALSO – American Express Gold Card Review – The Best Card for Foodies!)

If you do already have activity reservations, it’s worth calling and canceling. It’s always nice to give the tour operators a heads up. If you cancel your dinner reservation, the restaurant will be able to turn around and sell it again, rather than leaving the table open for you for 15 minutes. Having worked in the restaurant industry most of my life, we appreciate that!


Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers. Other links on this page may also pay me a commission - as always, thanks for your support if you use them
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