Traveling in 2021? Here’s What You Need To Know

By | Senior Writer
Last Updated: August 19, 2021
Thinking of Traveling in 2021? Here's What You Need To Know

It’s time to think about your travel plans for 2021. Perhaps you have travel booked, or maybe you’re just thinking about it. Either way, these are some travel trends and important things to know and consider before booking and traveling in the coming year and beyond.

Timing is everything

According to Forbes, picking the right time to travel (and to book) in 2021 and beyond is important. Those who book too soon may have to cancel due to border closures and travel restrictions. If you wait, prices may rise as there’s a crazy rush to travel.

It’s true — timing plays a big part in traveling in 2021. Taking trips in January of 2021 will be different from holiday travel in 2021. We can’t predict the future, but it may be best to consider fall and winter travel this year.

Whether we’re still in the throes of coronavirus or things have improved, taking a summer vacation is also never a bad idea. Plus, if COVID cases are still high, summer weather makes it easy to do outdoor activities, dine al fresco and social distance.

RELATED: Travel During COVID: Essential Tips For Flights, Hotels & More

Booking cancellable/changeable travel will still be key

Timing is a less stressful concern if you book cancellable or amendable travel. Airlines are making this easy for passengers. Carriers such as Alaska, American, Delta, Hawaiian and United have permanently eliminated change fees for standard economy and premium tickets. Hotels and rental properties are offering generous cancellation policies too.

It’s never been easier to cancel travel, just read the fine print and make sure to understand the cancellation terms before booking.

RELATED: Get Updates and Book Flight Deals as They Arise

Things To Know About Traveling in 2021
Did you know? You can browse and book pre-mapped-out itineraries with the Winetraveler App.

People will go further and stay longer

Jetting off every other weekend isn’t quite as easy as it once was. Travel takes a bit of conscious organization these days, from making sure your rate is cancellable to triple-checking border and arrival rules to getting travel insurance that covers COVID-19. 

Travelers may take fewer trips in 2021, but these trips may be longer and more curated. As airlines have dropped many routes, you may find it takes longer and requires a few layovers to get to your chosen destination. Once you’ve gotten your negative COVID test to show proof to enter a country, or carefully organized a socially distanced itinerary, it’s worth staying at your destination a bit longer after all that hassle. 

People may be traveling even further in 2021, too. After a year stuck at home, many have realized that if they want to take that bucket list trip, they have to seize the moment. 

We spoke to Chelsea Brown, founder of Millie, a company that curates female-focused travel to Jordan and beyond. She is confident that the far-flung, bucket list trip will return, especially because many people have had time to save during quarantine.

She told Winetraveler, “Because travel will initially take more effort, we’re going to be seeing those committed travelers out there first – those with wanderlust or family and business obligations. And they will have very specific destinations and thoughtful goals for their trip.”

“I also think that ‘bucket list travel’ will become very popular. We’re currently at home researching that dream trip we’ve been putting off and perhaps saving for a while in quarantine. Once travel becomes accessible again, our dream trip awaits,” Brown said.


And Brown isn’t alone in her opinion. When travel influencer and blogger Valerie Joy Wilson, aka Trusted Travel Girl, launched some 2021 group trips a few months ago, she was surprised and thrilled when they sold out almost immediately.

“I started with a Peru trip which sold out, and my Cambodia trip sold out within six minutes, “ she explained. “I think they sold out so quickly because people are stressed and want to travel, but can’t fathom planning anything at the moment. People want things planned, and they can show up, have a great time and not have to plan. People are willing to travel further and visit places they’ve always wanted to explore, but previously been too nervous to visit on their own. Covid has shown people that life is short, so book that trip.”

RELATED: Top Recommended Wine Regions To Visit in 2021

Working Remotely While Traveling

Working remotely and personal travel will meld together

Remote work is likely here to stay, regardless of how the COVID-19 pandemic evolves. And even now, many are choosing to work remotely in a different location, combining a vacation along with work.

There are many ways to do this in 2021. As long as you have a solid Wi-Fi connection and the right tech tools, you can work from anywhere.

We spoke with Nick Ellis, hotel expert and editor at The Points Guy, who told us he thinks the concept of work is forever changed.

“It stands to reason that companies will continue to allow flexible working arrangements, and thus give workers more opportunity to spend extended amounts of time in a different place so they can work and relax simultaneously. Americans are notorious for not taking full advantage of their vacation days, but the new normal with regard to working could change that, as more and more people realize they can be just as productive sitting poolside as they would be in their home office,” Ellis said.

If you’ve decided this sounds like a pretty good plan, the next step is selecting where to go. And the Caribbean is welcoming remote workers with open arms.

Take Aruba, which created the ‘One Happy Workation’ program targeting U.S. citizens. Visitors can get special rates at participating accommodations (many include Wi-Fi or all-inclusive meal plans) for up to 90 days. Barbados is offering one-year visas to anyone wanting to work from the Caribbean Island with their ‘Welcome Stamp‘ program. Antigua and Barbuda are offering a special ‘Digital Nomad Resident‘ program which offers a two-year visa to remote workers. 

And it’s not just destinations catering towards remote workers. Hotels are getting in on the digital nomad fun too — even large chains like Hyatt and Marriott. The Work from Hyatt program includes perks beyond just a hotel room, like a separate workspace, waived resort fees and daily food and beverage credits, among others.  The Work Anywhere with Marriott program offers varying passes; the most interesting is the play pass, which includes work benefits as well as vacation benefits for a combined business/leisure stay.

Ellis is especially intrigued by Hyatt’s new program.  “I’m excited about the Work From Hyatt program, particularly at its all-inclusive properties, like the Hyatt Zilara Cap Cana in the Dominican Republic, “ he told Winetraveler. “It’s a still-new beachfront property, and since it’s all-inclusive there’s no need to worry about ancillary costs for food and drinks while on the property, which makes your extended stay worry-free.”

Valerie Joy Wilson is also in agreement, saying, “With so many people working remotely, marrying a week of vacation with a week of working remotely is something we’re going to see a lot more of in 2021. People will actually be able to use their vacation time.”

So, grab your computer and consider spending part of 2021 basking in the Caribbean sunshine. After all, emails can just as easily be sent poolside, it seems.

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Preparing for travel during and after Covid 19

Staying healthy while traveling will still be a major priority

Health concerns in 2021 when traveling will mimic those of 2020. The main one?

You guessed it: COVID-19.

We spoke to Rebecca Wolfe Acosta, RN, MPH and Co-Founder/Executive Director of Traveler’s Medical about how you can stay safe and healthy while traveling in 2021. 

“This is not going away in 2021,” Acosta told Winetraveler, “Covid should be a big part of your travel planning.” And it’s true. The virus shows no signs of stopping, so you need to factor it into your travel plans by packing the right items (masks and sanitizer) and understanding the risks, as well as the rules and regulations of the destination you’re visiting.

She also suggests you ask yourself the following questions before traveling:

    • Do you know all the rules and regulations about entering your destinations? This could be things like entry requirements, curfews, mask mandates and more.
    • Do you have insurance? Does it properly fit your needs and cover Covid-19?
    • Are you willing to risk getting sick in a destination where you don’t speak the language or the culture is very different from your own?
    • Can you afford 14 additional days in a hotel to quarantine, or pay other bills that might pop up if you get sick while traveling? Don’t forget about the financial risks that may come along from contracting Covid-19 on the road apart from medical bills.
    • Have you gotten all your other vaccines? With so much emphasis on Covid, don’t forget about other important illness prevention. If you’ve packed the masks and sanitizer on your safari trip but forget to get malaria pills, you could end up extremely ill with something that isn’t Covid. Acosta suggests checking out your chosen destination on the CDC website before traveling out of the country for important information.

Acosta has a number of helpful tips when it comes to staying healthy on the road. She advises doing lots of research before traveling to understand the current risks, as well as the risks you may bring to a delicate community or emerging country. “People can be thoughtful when planning, and should find something that works for them and is safe for everyone involved,” she said.

She also recommends really doing your research when it comes to travel insurance. Make sure there’s a hotline you can call if you get sick. “It doesn’t matter if your destination has great care if you can’t get a hold of someone to guide you to it,” she added.

Finally, don’t expect a potential vaccine to be an immediate band-aid for Covid (and the travel industry). Acosta thinks that access to affordable and rapid testing may be a game-changer for the travel industry, at least towards the beginning of 2021 when a vaccine is unlikely to be fully deployed.

Travel in the Caribbean 2021 and Beyond

Plan to visit international spots that haven’t been closed to Americans

We know you may be dreaming of that epic Paris adventure or jaunt to Rome, but with recent coronavirus outbreaks plaguing a number of European countries, it’s worth it for some to be cautious.

But this doesn’t mean U.S. travelers are out of luck. Many Caribbean countries are (and have been) open to U.S. travelers for months now, like Belize, Mexico, St. Lucia and Aruba. Turkey and Croatia have also been open to visitors throughout the pandemic. 

It may be a safer option to consider travel to spots like these, rather than a risky bet on other EU countries.

RELATED: Browse Winetraveler’s Itineraries and Travel Guides to Start Planning Your Next Trip

What can you do to prep?

There are a few things you can do to prepare for 2021 travel. 

    • Research travel insurance policies.
    • Research destinations/hotels/activities/airfare for places you want to go to. Make sure to understand entry requirements and other rules before booking anything.
    • Put holiday purchases on a points-earning credit card to keep building up your stash of miles and points. We spoke to Sarah Silbert, Credit Card Editor for Personal Finance Insider, who gave us some useful tips when it comes to building up your points and miles balances. “Top rewards credit cards like the Chase Sapphire Preferred have been offering record-high sign-up bonuses to new applicants, and taking advantage of these deals could help you save money on travel when you’re ready to book a long-overdue vacation. Just remember that credit card rewards aren’t worth it if you can’t pay your balance in full each month — the key to using cards responsibly is to only charge what you can afford to pay off,” Silbert said.
    • Continue saving. One perk of traveling less is that maybe you’ve saved up some extra cash for a longer, fancier or more luxurious experience in 2021.

While it may still seem daunting to travel in 2021, it is a definite possibility to travel safely next year, especially if you keep these key considerations in mind. Happy travels!

If you enjoyed this itinerary, consider joining the Winetraveler Facebook Group for additional insight and travel inspiration around the world. You can also pre-register for the Winetraveler Wine Club to receive unique wines and itinerary suggestions to your door.

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