Your Guide to When, Where, & How

As fall and winter breaks approach, there’s still hope for a great getaway even if you haven’t booked anything yet.

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For many travelers, the 2020 holiday season was a bust (thanks, COVID). Does it have to be that way this year? Lingering uncertainty has lead to a last-minute decision-making mindset when it comes to travel. (We’ll blame the pandemic, though many of us suffered this affliction well before 2020.)

“Everyone has been playing the wait-and-see game,” says Joshua Bush, CEO of Bryn Mawr, Pennsylvania–based Avenue Two Travel, and a member of AFAR’s Travel Advisory Council (TAC). “However, it’s not the year for that strategy.”


Apparently, while some of us were dragging our feet on fall and winter travel, there were plenty of people who did plan ahead (curses), likely feeling the pull to get together with friends and family after a year of missed opportunities. Availability may be scarce in certain holiday hot spots and prices may be on the rise, but there is still hope.

“Many people booked trips for this year’s holidays and now that final payments are coming due, they are deciding to cancel for a number of reasons,” says William Kiburz, vice president of St. Louis–based Coronet Travel Ltd, another TAC member. Kiburz says that people who planned several potential holidays are now canceling the plans that didn’t make the cut; they may back out because of a lack of reliable flights or the crush of COVID testing requirements and preflight paperwork. (Their overplanning is our gain?)

“So, this can actually be a great time to look,” says Kiburz.

Travel advisors, insiders, and travel booking sites gave us the inside scoop on what availability is left, at what cost, and when and where to book holiday travel.

Tips for finding holiday travel deals

Repeat after us: Book your holiday travel ASAP. Say it again so we know you’re paying attention: Book your holiday travel ASAP.

“Pricing for holiday airfare at the moment is quite good,” says Willis Orlando, member operations specialist for airfare deals newsletter Scott’s Cheap Flights (a great way to track said holiday airfare deals). “We’ve seen more last-minute deals both domestically and internationally in the last few months. If you haven’t locked in your Thanksgiving plans yet, you may still have an opportunity to grab one of those $155 round-trip coast-to-coast flights we’ve been seeing pop up lately.”

Scott’s Cheap Flights warns that the odds of snagging low-cost tickets decline the closer we get to Thanksgiving. Once we’re about three weeks out from Thanksgiving, “you can expect prices to soar,” the service warns in its 2021 Thanksgiving Travel Guide.

Travel booking site Hopper agrees that time is of the essence to get a decent price for the holidays. Hopper recommends booking both Thanksgiving and December flights no later than Halloween. After that, airfare is expected to increase 40 percent leading up to the week of Thanksgiving, and for Christmas, the absolute last call for booking flights is Thanksgiving (November 25) .

Travel booking site Expedia reports that the most expensive travel dates around the holidays are the Wednesday before Thanksgiving (November 24) and Thursday, December 23. Those planning a post-Christmas trip should avoid departing on Tuesday, December 28.

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“Historically, shifting departure dates to the week before or after each holiday will yield savings. For example, departing on or before November 19 in 2019 resulted in a savings of nearly 15 percent compared to departing the day before Thanksgiving. For Christmas, departing between December 13 and 17 could save travelers more than 10 percent. Traveling on Thanksgiving and Christmas Day also often results in cheaper fares,” Expedia told AFAR in an email.

Canceled flights, vacation rental scarcity, and overbooked hot spots—how to handle holiday 2021 potential trouble spots

Getting desperate for a good deal? Consider flying on Thanksgiving or Christmas Day.

Service issues with flights and hotels

Let’s talk about the elephant in the holiday travel room: potential service problems. By now, you’ve likely seen or heard about the massive issues with flight cancellations (Southwest being the latest to make headlines). There’s some concern the issues may persist into the busy holiday travel season.

We’ll revisit some tips we shared in a recent story about flight cancellations to help travelers avoid getting stranded:

  • Book the earliest flight out you can. “The first flight of the day is more important now than ever,” says William J. McGee, an aviation expert and author of the book Attention All Passengers. “You should book that 6 a.m. departure,” as delays tend to pile up later in the day.
  • Try to take a nonstop over a connection, even if that means an increase in airfare. As McGee notes, “Why double your chances of a problem if you can avoid it?”
  • Get to the airport earlier than usual and prepare for crowded conditions—at all stages of the journey. “Travelers are facing unforeseen delays such as scarce parking and long checkpoint lines, long before they can get to a gate,” Southwest Airlines advises.
  • Build some buffer time into your plans. Hopper recommends that you “consider flying in a day early.” The company also offers a “rebooking protection” feature that gives travelers the option of choosing a flight on another airline if their flight is disrupted or canceled.
  • Know your rights as a flier. Airlines are not required to compensate passengers when flights are delayed or canceled due to problems such as bad weather that are deemed beyond their control. If your flight is canceled, you’re entitled to a full refund, even on a nonrefundable ticket, if the airline canceled the flight, not you.

With hotels, the issue is a slightly different one. It’s not that your reservation will be canceled, but that the service you receive when you get there won’t be up to snuff due to ongoing staffing issues.

“With rates in certain destinations higher than 2019 and service levels at an all-time low due to staffing shortages” travelers need to make sure their “expectations [are] aligned with the current environment,” says Avenue Two Travel’s Bush. Heading into the festive season, hotels and resorts could still have “reduced capacities, fewer food and beverage outlets, and less overall staff.”

Bush says this is where having a travel advisor can really help. Tuned-in travel sellers can secure dining reservations, spa appointments, and book private cabanas, “ensuring you still get the vacation you were hoping for despite service level changes. The way you traveled in 2019 is very different than the way you travel successfully today. Reservations have become compulsory when it comes to in-destination plans, especially on peak holiday dates,” says Bush.

Everyone is looking for snow and sun

Thinking of heading south of the border for the holidays? You’re not alone.

Because we clearly haven’t reinvented the holiday travel wheel, the majority of travelers this season are searching for popular ski resorts or chasing the sun in warmer-weather destinations like Hawaii, Florida, and Mexico, according to Expedia.

Part of the issue is that longer-haul international travel is still less attractive to many due to the pandemic—there are travelers who remain concerned about health and safety issues (including for as-of-yet unvaccinated children) or who are deterred by overwhelming COVID vaccine and testing requirements for international travel. That means some closer-to-home destinations are even harder or more expensive to book than they may have been prepandemic.

Another potential problem is that with the U.S. border reopening to European and other foreign leisure travelers and to travelers from Canada and Mexico crossing by land in November, the competition for reservations in popular domestic travel destinations is heating up.

Expedia reports that U.S. hot spots seeing strong demand for holiday travel this year include ski towns like Jackson Hole, Florida beaches, and national parks such as Yellowstone.

Kiburz tells us that for those struggling to find the right domestic holiday trip, Coronet Travel works with Alpine International “who can handle any ski or winter destination bookings.”

According to Hopper, the most popular domestic destinations for holiday travel—which in our last-minute travel book might be ones to avoid—are Orlando, Dallas, Phoenix, and Puerto Rico. For international travel, Cancun and Mexico City in Mexico are seeing a rise in bookings.

Vacation rentals

Airbnb reports that Oahu is among its most searched destinations for the holidays.

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You know what could be great this holiday season? Let’s get the family or some friends together in a house to celebrate making it through a pretty awful 18 months. Sound like a good idea? Yeah, it did to everyone else, too. Vacation rental behemoth Vrbo tells AFAR that “travelers started locking in their holiday rentals as early as July.”  

There’s been a 45 percent increase in demand for Vrbo homes near ski resorts, when compared to 2019, and warmer beach locales have seen more interest, too, which means it’ll be harder to find homes in some of the most popular snow-filled and sun-drenched destinations.

Vrbo suggests looking into alternative ski destinations, such as Winter Park, Colorado; Mammoth Lakes, California; Pocono Mountains, Pennsylvania; and Gatlinburg, Tennessee. Be sure to check our après-ski guide for additional ideas on where to go to embrace winter activities and the post-slopes scene.

The top-trending destinations (read: ones that could give you booking problems) on Airbnb for the Christmas holiday time frame are:

Maybe this is the year to plan a road trip to a more under-the-radar state park, to one of these alternatives to the most popular national parks, or to one of our favorite U.S. small towns instead.

Holiday 2021 travel alternatives

New York can be magical in winter.

Big cities for the big holidays

Some of our favorite cities—New York, San Francisco, and Boston—continue to “offer up some the best deals around in terms of hotel prices, with savings for the holidays ranging from 10 to 35 percent compared to 2019,” Expedia reports.

“If you’re headed to a city that historically has relied heavily on business travelers such as New York, Chicago, or San Francisco, you can expect broad availability and lower prices than in years past,” says Scott’s Cheap Flights’ Orlando.

He notes that in Northern California’s Bay Area, prices are still down more than 30 percent compared to prepandemic levels, “as a dearth of business and international travelers has left loads of hotel rooms open.” 

Head to newly opened and far-flung international destinations

Fiji is opening to vaccinated U.S. travelers on December 1. We’re just saying.

For those willing to jump through some international travel hoops (COVID vaccination and testing requirements among them), some of the most newly opened (to U.S. travelers) destinations may offer a great way to get away from the crowds.

In recent weeks, international locales including Argentina, Canada, Chile, Fiji, Singapore, and Thailand have all announced reopening plans, meaning now is the time to book before travel there starts really rebounding.

Kate Doty, managing director of Geographic Expeditions and an AFAR TAC member, says she can still book clients in destinations that include Thailand, Nepal, India, Sri Lanka, Maldives, Kenya, Tanzania, Zambia, Zimbabwe, Namibia, South Africa, Jordan, Turkey, Mexico, Panama, Fiji, Chile, Argentina, and Colombia this holiday season.

Costa Rica has less availability than the above destinations, but she said she can probably still make it happen.

“If you are open and have time, there are amazing adventures available,” she advises.

International travel during the COVID-19 pandemic

International travel requirements and restrictions continue to evolve throughout the pandemic. Check the U.S. State Department’s detailed COVID-19 travel information and country-specific advisories, which are updated regularly. We often cross-check these references with entry requirements that are published by each individual country’s foreign or public health affairs office for the latest.

Additionally, all international passengers age two and older flying into the U.S. (including returning U.S. citizens and permanent residents) must provide proof of a negative COVID-19 test procured within three days before boarding their flight to the United States.

The CDC also has detailed recommendations for travel during the pandemic, both for vaccinated and unvaccinated travelers.

Barbara Peterson contributed reporting.

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