When is the best time to book holiday travel this year—if at all?

Many people are looking to reunite with their loved ones for the holidays—perhaps for the first time this year given COVID-19. And with the airlines in dire straits, there’s a common assumption that booking travel in general this season will be cheaper because of the pandemic. But this is not necessarily true.

Pre-pandemic, the best time to book holiday travel was typically pegged at around three to six weeks in advance. But this year—as if you needed to hear or read this one more time—everything is different.

Jeremy Prout, director of security solutions at International SOS, a global medical and travel services firm, recommends booking now (or by mid-October at the latest) for flights and hotel accommodations during the month of December 2020. And flight and hotel availability could be limited owing to either border restrictions or economic impact—so either way you want to ensure your reservation.

“There are a lot more risks and protocols to take into consideration, and that’s why planning far in advance of your expected departure is the safest bet,” says Prout. “Knowing these guidelines can change at the drop of the dime, it’s also important to continuously monitor those health guidelines on a regular basis and right before you leave for your trip, just in case anything changes.”

Even for domestic travel, many U.S. states have issued mandatory quarantines so it’s important to brace for the possibility of a quarantine if you are going to travel to another state, notes Brian Kelly, founder of the popular U.S.-based travel site The Points Guy.

“If you’re planning to fly home for the holidays, or are still hoping to take your annual holiday season vacation, know that you’ll need to do way more research than you normally would—and take more risks,” Kelly says.

Still, while 2020 is fraught with new challenges and decisions when it comes to travel, Kelly says some deals have started to return, so now might be a great time to use points and miles.

“There are definitely deals out there right now, and if you decide to travel for the holidays, it may cost fewer miles than it has over the past few years,” Kelly says. “For example, if you want to fly from Newark to Miami for Thanksgiving, it’ll cost you just 5,000 United miles to fly the Thursday before Thanksgiving or just 6,000 miles to fly on the Saturday before. Keep in mind that even though there isn’t currently a mandatory quarantine upon arrival in Florida, there will be one coming back to New Jersey. On American [Airlines] through much of November and December, you can fly from Houston to Jackson Hole [Wyo.] for just 10,000 miles each way.”

A good rule of thumb, according to Kelly, is that traveling on the holiday itself—such as Thanksgiving, Christmas, or New Year’s Day—will usually get you the cheapest rate, and that’s generally true every year.

However, keep in mind that while many locations are reopening, COVID-19 is still a huge threat on a domestic and international level, so part of travel preparation should include doing extensive research on health guidelines at the destination and any other areas you may be stopping by or returning to prior to booking accommodations.

Airlines and hotels have taken extraordinary measures to ensure safety during the pandemic, Kelly says, but he concedes there is still a level of risk, adding it could be good to contact your doctor for additional guidance before departure. “But that being said, I have traveled safely to Croatia, Antigua, and Tahiti and have had incredible trips with minimal crowds,” Kelly notes. “I have had the ability to explore once-crowded and touristy places nearly to myself, so there is a reward for travelers willing to travel this year—and there is a ton of award seat availability.”

“Travelers also need to consider the financial obligations that could arise with an unexpected quarantine [or] border closure, such as lodging and meals, as well as consider what implications on your career could be, should you become sick on the way home from travel and need to quarantine for two weeks at home,” Prout says.

If your flight is canceled by the airline, you are entitled to a full refund, Kelly notes. And if you choose to cancel your flight reservation, and the flight takes off, most major U.S. airlines—including United, American, Delta, Alaska, Hawaii, and Southwest—have permanently dropped change fees for most domestic flights. Still, if you want to make sure you can cancel your trip for any reason, The Points Guy recommends that you purchase “Cancel for Any Reason” insurance. However, as Kelly explains, this is the most expensive option, so be sure to first weigh the option of changing your trip to another date given that there are no longer any change fees. 

Travel insurance could be a good idea in some scenarios, but it’s not always a guaranteed safety net. Prout specifically suggests purchasing insurance for any airline travel taken during the pandemic: “With that said, insurance policies vary from company to company, so it’s important to contact flight insurance providers—or if purchasing insurance via the airline, contact the airline—prior to purchase to discuss COVID-19 policies and have a full understanding of what they are able to do or will cover in an instance such as a flight cancellation due to a border closure.”

For travelers who fail to reach out to insurance providers or the airlines before departure to confirm what can be refunded or credited in the case of a COVID-19 related cancellation or border closure, Prout recommends the following three steps. First, if travelers have purchased travel insurance, they should contact their insurance provider to determine next steps. Second, if you purchased your trip on a credit card, you might be able to cancel or get a refund for the tickets purchased through the credit card company. In some cases, the credit card provider could be able to help with even a partial refund, if not a full refund. Third, for business travelers especially, keep your managers (as well as your family) in the loop about your travel plans. If you are short on financial resources at any step of the way, your contacts back home might be able to book return flights on your behalf or provide emergency funds.

Regardless, International SOS continues to advise against nonessential travel during the pandemic. Though Prout says the firm recognizes that with the upcoming holiday season, it’s likely that many people will be looking to travel in order to be with family and friends.

“If you do choose to travel, it’s important to evaluate your own risk level, which you can do by looking at your personal health (age, weight, physical shape, underlying medical conditions, etc.), as well as the risk level of anyone you are going to visit,” Prout says. “For example, if someone you are going to visit is elderly, or has an underlying health condition, they are considered high-risk, and I would strongly advise against traveling to visit them at this time.”

Experts stress continuing to follow CDC guidelines for curbing the spread of COVID-19, including practicing good hygiene, wearing a mask at all times when visiting areas outside your home, and not traveling if you’re feeling sick. (A full list of mitigation measures can be found on the CDC website.)

But in the case you or a traveling partner become sick and test positive for COVID-19 while in transit, you will need to find an isolated location to quarantine for two weeks, as well as enough personal protective equipment (PPE) and medical supplies to sustain yourself.

“Although there are several tracking tools to predict where the next outbreak will occur, the reality is that a COVID-19 outbreak could happen at any time and any place, and local government leaders can impose restrictions and change guidelines quickly,” Prout says. “Travelers need to anticipate those various instances that could happen, should one of the locations they are visiting, traveling through, or even returning home to, have a sudden outbreak.”

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