36 Invaluable Holiday Travel Tips and Hacks for 2021


Planning a trip is daunting even under the best of circumstances. But sprinkle in a pandemic and a few of what are, historically, the worst days to travel each year, and you’re looking at airfare at a premium, a rental car shortage, an inevitable abundance of cancellations and delays and, of course, all of the subsequent crowds attempting to navigate the same set of ever-changing rules and regulations that you’re facing. Yes, we’re talking about the holidays, which, in case you needed reminding, are right around the corner.

Last year, despite the predictions of experts and against the CDC’s advice, millions of people flocked to the airport during the week of Christmas, with more people traveling through security checkpoints in a handful of days than they had since mid-March. They were unprecedented times met with exactly the outcomes you might expect: long lines, delays, missed flights, angry passengers and, later, corresponding outbreaks.

That said, we’ve been at this for quite some time now, which means we have the experience and foresight to know what to expect this year. The general consensus? It’s going to be even crazier. According to data collected by Kayak, while travel interest for the winter holidays is still slightly down compared to 2019, they’re seeing significant momentum around international and domestic flight searches when compared to 2020 (up 155 percent and 212 percent, respectively). So buckle up. 

“While there are some travelers who feel they are not ready to travel due to the Delta variant, there are countless others who see the pandemic as a longterm chronic issue that will not prevent them from traveling,” says Damon Corkin, Founder and Travel Director of Andean Discovery. “Many travelers are realizing that whether it’s a trip to the local grocery store or a trip on a plane, the same inherent risks exist as soon as you take a step outside your home.”

With that in mind, and to make things moderately less frustrating, we went ahead and asked a panel of expert jet-setters — agents, bloggers and various other industry professionals — for their top tips and tricks for navigating a rockier-than-usual holiday season. The result is a compendium of wayfaring wisdom that will make budget-friendly holiday travel feel more accessible and the process as a whole more palatable.

As long as you book soon. Like, now. Because you really, really need to book now.


1. Prepare for tighter regulations surrounding vaccination and air travel
“I don’t expect to see as many cancellations (after all, this industry also has to recover). However, the rules will be very strict and only those who can prove they are protected against the virus will be able to fly freely.” — Torben Lonne, DiveIn

2. Do your homework on entry requirements early and often
“Keep in mind that travel restrictions have been changing quite often, so make sure you’re up to date on the current requirements at your destination. This is especially important for international travel, as entry requirements could be different in two to three months.” — Steve Oliverez, InsanelyCheapFlights.com

3. Expect an increase in airfare
“Since there will be less travel routes available, there will definitely be an increase in the price of airfare — particularly if airlines [move to prevent] unvaccinated passengers. Book tickets at least a month or two months in advance. Sales on flights usually happen around midnight.” — Dan Alder, Levvvel

4. … but keep an eye out for the occasional deal
“A lot of airlines added flights in the summer as travel rebounded, but then the Delta variant took the steam out of that rally. Travelers should be on the lookout for rare deals on airfare, as some routes may have been recently added but not filled yet due to variant fears. Once flights are full, prices should skyrocket as they usually do this time of year because even with new routes there are still fewer options than pre-pandemic and airlines are still trying to make up for financial losses incurred in 2020 and 2021.” — Chris Atkins, Central America Fishing

5. Consider going south
“Among Kayak’s most popular destinations for the winter holidays, 5 out of 10 of the most affordable flights are down South, including Nashville (#1), Austin (#5), Dallas (#7), Miami (#8) and Atlanta (#10), all with airfares under $315.” — Kayak

6. Search for flights on Sunday
“You can get the best deals by booking tickets on a Sunday. Evidence shows ticket rates during Sundays are at least 30% lower than those posted on Fridays. Airlines refresh their ticket prices every week. As such, they jack up the rates toward the end of the work week to utilize the current ticket pricing range.” — Michael Jeffcoat, The Jeffcoat Firm

7. Be flexible
“Flexibility is key! I have a teacher couple planning a delayed honeymoon over their Thanksgiving break and space is very limited. But by flying on Thanksgiving day it saved thousands in airfare. Their feeling was they could have a turkey dinner anytime but now is the only time they can book that dream honeymoon suite with the savings. I am also finding great rates the week prior to Christmas. Since so many are still working virtually, why wait until the day after Christmas?” — Sarah Kline, Time For Travel

8. Book your Thanksgiving and Christmas flights yesterday
“Thanksgiving flights should be booked between 30-60 days in advance of the holiday. Booking within this period will most likely get you a better Thanksgiving deal in comparison to the weeks leading up to the holiday. For more generous fares, look to fly on less-popular days — most notably, Monday, November 22. Avoid flying out on Sunday, November 28 — it’s so expensive. Based on past history, December holiday flights are best booked mid-September. But the month has already passed, so I recommend booking as soon as possible. Book more than three weeks before Christmas, as within those first three weeks of December, prices dramatically go up for holiday travel. If you can, opt to fly out on Christmas Eve, as prices are normally lower then — I advise avoiding traveling on Sunday, December 26, as prices are super high on this date.” — Brandon Berkson, Hotels Above Par 

9. Use third-party booking sites
“I have three pieces of advice: Download fare-tracking apps like Hopper. When searching for flights, use websites that compare different airlines and third-party booking engines — my favorite is Kayak. And for the December holidays, book your ticket before December 1.” — Brandon Berkson, Hotels Above Par

10. Familiarize yourself with individual airline policies
“American Airlines and Southwest airlines will be the heavily booked airlines because Southwest has a lenient cancellation policy, and American Airlines is offering no-fee cancellation for all tickets that are higher than basic economy. However, these are the only two airlines flying out of the U.S. that have a sufficiently lenient cancellation policy, and the ‘value’ tickets will likely book quickly. I would recommend anyone booking an international flight and plans to use these airlines, and anyone who doesn’t want to pay for a first-class ticket to book at least two months out.” — Carlos Grider, ABrotherAbroad 

11. Consider alternatives to commercial aviation
“Scheduled airline services are still operating at a reduced capacity, which along with a shift in people’s overall travel behavior, has assisted in the boom in demand for private jet charters. Travelers are also still turning to private charters due to the increased safety and health precautions they provide from COVID. Private jet companies have been experiencing a diminished supply of aircraft and have had to increase prices, so we recommend booking travel arrangements for this method of air travel as soon as possible.” — Air Partner

12. Know which days to avoid
“Based on current and past inquiries and bookings, we can predict the busiest days for Thanksgiving travel will be Wednesday, November 24th and Saturday, November 27th, and Thursday, December 23rd, Sunday, December 26th, and Saturday, January 1st for Christmas/New Year’s travel.” — Air Partner

“This year, November 28 is expected to be 2021’s busiest travel day, which falls the on the first Sunday after Thanksgiving. Currently, the team at CheapCaribbean is expecting to see an increase of roughly 70-80% more consumers traveling this holiday season compared to last year, however they are still anticipating fewer travelers than 2019 due to ongoing travel restrictions and concerns. The team is expecting resorts to have more last minute availability this holiday season than in 2019, but still advise travelers to book soon.” — CheapCaribbean

13. Get PreCheck or Global Entry
“Be prepared for long lines and bring your patience along with your carry-on luggage. Check your passport’s expiration dates. Also, Global Entry/TSA/Clear are all products we highly recommend as well as Airline Lounge privileges.” — Phyllis Polaner, Smartflyer


14. Stay at a smaller hotel or resort
“My prediction is that smaller resorts or isolated accommodations will be the most popular because they allow people to stay safe during their trips, away from big crowds. It is much harder to implement safety measures in a large hotel, which is why travelers may choose alternative accommodation options.”— Torben Lonne, DiveIn

15. Know your cancellation policy before you book
“Book hotels and car rentals on platforms [e.g., Hotels.com] that allow you free cancellation so you can squat on something today and then that gives you a little bit of time without rushing to double-check other options.” — Kara Harms, Whimsy Soul

16. Don’t expect an upgrade to be available at checkin
“Book the room category you want, not one with cheapest prices. Upgrades will be far and few between. Ask your travel professional for added amenities that will add value to your stay and relax and enjoy!” — Phyllis Polaner, Smartflyer

17. For a less restrictive holiday, consider a private home rental
“Despite the Delta variant, we are seeing an influx of holiday bookings and we are nearly completely booked. From our perspective, with private home rentals, we are seeing extended families opt for private home vacations where they can enjoy the traditions of Christmas without the restrictions of a hotel setting. These private home rentals are going fast, and travelers need to book now. [We’re also seeing an influx of] travelers who are ditching common city destinations and opting for experiences in nature or booming towns near National Parks.” — Larry Mueller, Cuvée

18. Expect outdoor destinations to be more popular than usual
“Since the onset of the pandemic, outdoor travel has become the go-to vacation as travelers look for affordable, accessible and less crowded alternatives to hotels or homes. We know now that the camping boom will remain steady throughout the holiday season — in 2020, trips booked on Pitchup.com between October and December increased by 111% from the same period in 2019. Based on last year’s steady bookings during the holidays, I expect that travelers this holiday season will seek nontraditional accommodations like campgrounds, RV parks, camping pods and other unique options to protect their wallets, avoid heavily trafficked hotels and find relief from ‘cabin fever’ — and select family members — right in the heart of nature.” — Dan Yates, Pitchup.com

“Although we’ve come a long way in this pandemic, it’s important to remember it’s still not over, so I think families and friends are still going to be focused on finding creative ways to gather safely through group activities like skiing, hiking and other outdoor recreational pastimes. So, in correlation to all this pent-up travel demand, things will only get more hectic and expensive day by day, as more people book these ‘making-up-for-lost-time’ trips.” — Brandon Berkson, Hotels Above Par

Car Rentals

19. Book you car rental the day before yesterday
“Rental car searches and prices for the holiday season (November 12-January 7) are up across the board compared to both 2019 and 2020. In fact, rental car searches are already up 230% compared to 2019 and up 243% compared to 2020. Prices follow a similar pattern, with the average cost per day seeing a 75% increase compared to 2019 and a 66% increase compared to 2020. Kayak typically recommends booking your rental car two weeks in advance for a good price (based on 2019 data). But given the shortage we saw this summer, you may want to plan further in advance to ensure you’re not left without one when you need it most.” — Kayak

20. Beware your cancellation policy
“There was an incredible shortage of rental vehicles throughout this summer travel season, and rental companies haven’t been able to meet the demand yet. This problem is unlikely to be resolved by the holidays, so if you wait, there’s a good chance you won’t be able to rent anything. Right now, you can secure a rental vehicle for the holidays, so do it now. Currently, a rental economy-size car costs between $230 and $575 for a week. Make sure to choose an option that lets you cancel your reservation without penalty so that you have the option to change your plans without charges.” — Melanie Musson, AutoInsurance.org

21. Expand your search and look for bundles
“If you can’t find the car type or price you’re looking for, consider expanding your search to include neighboring cities. [Another] common mistake travelers make is booking trip components separately when they could maximize savings by bundling bookings into a package deal. For example, those who need both flights and a hotel can often find better deals, potentially saving hundreds of dollars, by booking them together.” — Christina Bennett, Priceline

22. Know that vaccine and testing requirements are not exclusive to air travel
“Many rental car companies require proof of vaccination or a negative PCR test. We ran into this many times throughout our travels over the past year. This was surprising to us; we knew that airlines required this kind of testing, but didn’t realize that many car rental companies expect the same thing.” — Laura Peters, Laura & Mike Travel

23. Mind the startups
“Instead of going to traditional car rentals, look for startups like Kyte that have a better fleet of vehicles always available for them.” — Jonathan R. Smith, CamperGuide.org

24. Familiarize yourself with peak travel times
“More drivers are now on the roads than even before COVID-19 – so you’ll likely have plenty of company on your holiday road trip. The new rush hour is Thursdays at noon, not Monday mornings, so plan holiday travel accordingly.” Arity


25. If you can’t find what you’re looking for, consider a travel agent
“I know this sounds self-serving, but it’s true now more than ever before — work with a travel advisor! We have relationships with suppliers and we are aware of where the deals are and when you can take advantage of them. In addition, we can often get better rates than travelers can get on their own.” — Lauren Doyle, The Travel Mechanic

“More travelers will use planners: A study by the ASTA (American Society of Travel Advisors) found that after the pandemic is over, nearly half of travelers (44%) are more likely to use a travel advisor (as compared to 27% of travelers who always or often used a travel advisor prior to the pandemic), suggesting an increased demand in organized travel. With ever-increasing confusion tied to COVID testing mandates and travel restrictions, many travelers are still quite risk-averse.” — Mark Hoenig, VIP Traveler

“If you’ve never used a travel professional before, now is the time. They know the best, most reliable flight patterns, and will be connecting directly with the property to ensure your room is right. They can even get you added, sometimes exclusive, amenities.” — Phyllis Polaner, Smartflyer

26. Travel with cash
“I would advise travelers to take extra cash with them as COVID has proved how unpredictable the market can be in recent times.”— Finn Cardiff, Beachfix

27. Get the travel insurance
“It’s important that those booking holiday travel consider travel insurance, and not the kind you buy at checkout during the flight booking process — the kind that offers comprehensive coverage for flight delays caused by the airline for things like breakdowns, bad weather, and your unexpected or involuntary quarantine. Additionally, travelers should consider trip cancellation insurance that covers lost, prepaid travel expenses if they contract COVID-19 and can no longer go on their trip. As always, Cancel for Any Reason (CFAR) travel insurance provides the most flexibility to travelers.” — Amanda Hand, G1G Travel Insurance

“The most important thing we are adding on is Travel Insurance and Emergency Policies. Even if you’ve never taken out travel insurance before, DO IT. Many destinations are actually requiring it now for entry: Trip Interruption for any extended stays (including testing positive and not being able to return home … most of the better policies will cover the costs to a specific daily limit), medical coverage to pay for any hospital bills, and medical evacuation coverage, especially some of the Caribbean destinations that have limited ICUs.” — Phyllis Polaner, Smartflyer

28. If you don’t have a valid passport at present, you may be SOL
“Travelers should also be aware that it’s taking longer than usual to receive updated passports. The ripple effect of COVID-19 and the economy of scarcity along with worker shortages has created a massive backlog of between 1.5 and 2 million passport applications, according to a Travel + Leisure article. In fact, the U.S. Department of State, which issues passports, reports that routine service can take up to 18 weeks from the day an application is submitted to the day a new passport is received. If you’re planning to travel abroad for the holidays this year, and your passport is currently expired, you may need to stay closer to home.” — Greg Jung, Seven Corners

29. Push your big trip to after the holidays
“The best piece of advice, if you are looking to take a vacation (as opposed to wanting to spend time with family), is it’s best to avoid travel over Thanksgiving weekend, Christmas and New Year’s. If you can swing it with work, try to travel in early December or mid-January instead. While it’s tempting to want to make use of the ‘free’ days off for public holidays, you will pay up to three times as much for the privilege.” — Joshua Borenstein, VIP Traveler

Destination Specific

30. Expect crowds if you’re headed to South America
“Holiday travel this year is far exceeding holiday travel in 2020. Thanksgiving has never been a busy travel season to South America; however, due to both re-bookings (guests changing their travel dates from Fall 2020 to Fall 2021) and last-minute bookings (guests booking within 90 days of a trip), Thanksgiving 2021 is shaping up to be quite a busy week. The number of groups we have traveling in November 2021 is double the number of groups who traveled with us in November 2020, primarily due to vaccinations and borders reopening.” — Damon Corkin, Andean Discovery

32. Miami and Chicago are calling
While travel prices have largely rebounded to, and in some cases above, 2019 levels, domestic round-trip flight prices are down about 20% for the holiday season compared to 2019. Miami and Chicago are the most affordable options this holiday season, with average round-trip airfares clocking in at $239 and $240, respectively.” — Christina Bennett, Priceline

32. There are great deals to be had in the Caribbean
“The Caribbean and Mexico are hot! The proximity and openness to U.S. tourists combined with recently added flight routes is likely driving the search interest behind this year’s top holiday hotspots with 6 out of 10 trending destinations within the Caribbean and/or Mexico. Punta Cana, Cancun, St. Thomas, Cozumel, St. Lucia and St. Maarten are all seeing an increase in search share of at least 79% compared to 2019. Flights to Latin America are on sale. If a trip to Latin America has been on your bucket list, this holiday season is the time to go, with price drops between 19 and 30% to some destinations compared to 2019.” — Kayak

33. … but you should still avoid peak travel weeks
“For Marriott in the Caribbean and Latin America we are seeing solid demand for the weeks of November 21 (Thanksgiving) and December 18 onwards up until January 7 (Christmas). Travel last year was quite restricted and many were not able to or did not choose to travel. An important point to note is that travelers are extending leisure trips, which is reflected in longer stays around Thanksgiving and the holidays.” — Diana Plazas, Marriott International Caribbean and Latin America

34. If you want some peace and quiet, avoid the following places:
“The 2021 holiday season is seeing the second highest increase in travel bookings since 2020, with a 43 percent year-over-year increase (and is expected to continue increasing). Travelers are flocking to Florida, Hawaii and the Caribbean, with Hawaii taking the #1 spot as the destination with the highest number of bookings. Top destinations for Thanksgiving are Florida, California, Arizona, South Carolina, Colorado, Nevada and Utah. Top destinations for the winter holidays are Florida, Hawaii and the Caribbean. Ski season travel is also already up 204 percent from last year, RedWeek’s best year on record. This isn’t just a pandemic anomaly; there are three times the bookings we saw this time in 2020.” — RedWeek

35. Don’t forget about your boat
“We’re seeing boat charters, tours, and other water experiences booking like crazy in many Caribbean destinations over the holidays. Usually, boat rentals in these locations don’t book this far in advance but we are seeing surges over Thanksgiving week and at the end of the year for Christmas/New Year.” — Val Streif, GetMyBoat

36. Go where the other travelers aren’t
“I am advising clients to consider destinations that are less popular. Destinations that are less popular are ones that are international and/or have a vaccine/COVID testing requirement. The harder-to-enter countries turn off other consumers, meaning if you are willing to go through the hoops, you can score yourself a deal and pretty awesome vacation.” — Lauren Doyle, The Travel Mechanic

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