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Tips for Remote Work

Remote Work

When I started a wedding and travel planning company last year, I never would have imagined that I’d still be telling people not to travel to certain destinations or that they should be cancelling their weddings to safely elope instead in 2021. Even though The Nomad's Direction specializes in planning COVID safe weddings and vacations, it still took a lot of research and trial and error to get to a place where I felt comfortable telling people they could travel. As the pandemic continues on and many of us have returned to our old jobs or new ones, it's inevitable that some of us will be asked to travel for work, may be looking to become digital nomads, or may simply need a change of scenery from our home offices. 

But there is hope! Many destinations are beginning to offer select deals to digital nomads in hopes that they will be able to repair the tourism economy in areas that rely heavily on it. Places such as Madiera, Portugal, Bermuda, Barbados, Antigua and Barbuda, Aruba, Mauritius, and even the United Arab of Emirates, rely on tourism to sustain their local economies. Many are offering long term work visas to ensure that digital nomads can safely work and travel while creating or giving back jobs to the locals. 

As vaccinations become more widely available and travel becomes a more feasible option for remote workers in 2021, it’ll be important for everyone to continue being vigilant about safety in public spaces when traveling. Airlines have been stepping up with enhanced cleaning protocols, new executive orders have been signed in the US regarding regulations for domestic and international travel, and The Mayo Clinic released tips on safe travel during COVID. For those of us who need to work while on the road, things such as these can help keep us and others safe while stimulating the hard hit travel industry. 

In my line of work, I have to travel often, whether it’s to coordinate elopements and micro weddings around the country or going on research trips to locations that my clients request often. One of the locations that kept popping up this year was Costa Rica. From early on, Costa Rica offered a great place for honeymooners and digital nomads alike to participate in outdoor activities, stay in eco-lodges away from others, and to simply recharge on the beach or on stunning jungle hikes. It was also one of the few countries that was allowing United States citizens with little to no requirements and no proof of negative COVID tests (at the time of writing). Many of my Costa Rica inquiries focused on adventure tourism, specifically surfing and yoga retreats, so I began reaching out to different companies that were taking COVID seriously and doing what they could to help the local economy at the same time. One of the biggest things I look for when planning travel for others is how they are dealing with COVID safety measures regardless of what the country’s requirements are. I found Surf With Amigas and loved that they were requiring negative tests even if the country was not and that all of the included activities were outdoors and socially distanced. Staying just steps from the ocean on 500 acres of protected jungle land didn’t hurt either! 

Even when I’m traveling for fun, running my own business means there's always a new client to contact, a future trip to plan for someone, or a wedding timeline to work on while on the road. I’ve found there are some key tips for traveling safely in 2021 and still getting your work done:


Before booking travel anywhere, it’s important to do some research on your destination’s entry requirements, quarantine rules (if any), and restrictions about what is open and what you’re allowed to do. Keep in mind that restrictions are always changing so you’ll need to be prepared to make changes at the drop of a hat. It’s important to follow CDC safe travel tips no matter where you go. I like to start my research on different requirements for travel on  the International Air Travel Association’s interactive international COVID regulations map. You can search by country and see up to date information on what the various restrictions and requirements are. Once you have an idea of the restrictions, go to your destination’s government websites to confirm them.

When I booked my trip Costa Rica was not requiring a negative COVID test for entry and the United States wasn’t requiring one for re-entry. A few days before we left, things changed and suddenly the US needed a negative test to let me back in! I ended up having to change my flights to accommodate for time to get tested in San Jose before returning home. It wasn’t my initial plan, but by being flexible and keeping a cool head, I was able to make changes to my trip in about 20 minutes! Surf With Amigas ended up being able to get a doctor to come to us, so I ended up getting an extra day in the city. As travelers, most people are used to last minute changes, but it’s important to be prepared for them. Have a backup plan when planning travel and use your research to have an idea of things that could change while you're away.


It’s weird to say, but by packing extra masks, snacks or items you might need, you can cut down on the amount of time you have to spend out in a crowded store or market. By now we’ve all been in the situation where we went to put on our mask before entering a public space only to realize we’ve lost it. If you know you have an extra mask or two in your bag it’ll make things a lot easier and safer. The same goes for packing extra items like snacks, reusable water bottles and the like. In addition to being able to pull your favorite treats out of your bag wherever you're working, you can also avoid unnecessary shopping (and hopefully save some money for your next remote work trip).

Working in Costa Rica


In an ideal world, everywhere we travel would have wifi, but that’s realistically not the case. Gone are the days of realizing your AirBnB wifi is out and popping out to a local cafe to get some work done. Where I live in NYC, we just started being allowed to dine indoors, let alone sit in a small cafe all day sipping coffee and answering emails! While planning my research trip to Costa Rica, I had to accept that due to the remote location, WiFi would be nearly non-existent. I was able to plan my work schedule accordingly beforehand, spending my time drafting blogs, editing photos and videos and working on wedding timelines for my clients. But even if I don’t know I won’t have WiFi on a work trip, I always try to set myself up with things I can do with no internet before leaving, just in case. 


Chances are if you’re traveling for work in a more vacation focused destination, you’re going to want to explore and unwind. When I work from the road I like to make a short To-Do list for each day. If you’re not into lists, block out some time in the morning or evening when you know you can work. If you know there’s a boat tour in the afternoon that you want to check out, spend some time working beforehand so you’re not stressing about everything you have to do while not working. It’s different depending on the type of work you do, but for me, I put experiencing all the location had to offer at the top of my priority list during the day, then do my more computer based work in the evenings when I’m able to focus. By doing it this way I’m able to report back to my clients with an honest and accurate review of the location and activities, but I still get my normal every day work done as well.


Whenever I travel for weddings, I pack one blazer, two shirts and multiple pairs of jeans and trousers to make the most out of the items I pack. When I travel for fun or on a work/fun trip like Costa Rica, I make sure to pack clothing that can be worn day and night, depending on how you accessorize. But the best multi-use item I’ve found for traveling for work is my Knack Bag! Before I got my Knack Bag, it wasn’t uncommon for me to have a computer bag, my camera bag, a tote bag with clothes, and another bag full of wedding equipment on any given day. I love that I can pack everything I need for a week-long trip and then easily convert it to a regular backpack for day trips or meetings. 

No matter where you work or what you do, we can all work together to travel safely in 2021!

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