Working Remotely: How to Plan a Long-Term Trip

Congratulations! You applied to a handful of remote job listings, proved that you have the skills to work remotely, and signed an offer letter. What could be better?

Many people choose to work remotely for a variety of reasons that include flexibility, staying at home with the kids, and working from your pajamas. You decided to work remotely for one reason in particular: the ability to travel.

Regardless of if you’ve spent time traveling in the past, living the working nomad life is an entirely different experience. You can no longer be a simple traveler because travel is now your life. Do you know how to balance work and travel simultaneously? Do you know how to maximize your productivity in a new place and not become disorganized? Experienced travelers might not think those are important questions, but they are. You might not believe that you need travel planning advice, either. However, no matter how much you’ve traveled in the past, being a vacationer is very different from being a working nomad. Here are some tips to keep in mind.


Getting Your Worker’s Visa

Visas (not the spending kind) can be a tiring and complicated issue. They have comprehensive rules and regulations that vary depending on the nation, so it’s imperative that you deeply research what’s required for your destination in question.

If you’re lucky enough to get a visa on your arrival, then it’s taken care of for you, and you don’t need to worry. Otherwise, you need to investigate the rules for applying for a visa. You might need to go through an agency, or possibly through the local embassy. You should also prepare all of the documents you might need to get your visa while doing your research. Typically, documents such as bank statements, airline tickets, and proof of hotel/accommodation are required. If you don’t have these, the company you work for should be able to provide them.

Ensure that you don’t leave applying for your visa until the last minute. You could find yourself in a sticky situation if you do. Make sure that the embassy has enough time to process the visa to save yourself the trouble.

Also, remember that having a visa might allow you to stay in the nation longer than having a visa-exempt stamp. Some countries allow you to stay for 30 days without a permit, but you can stay for an additional 30 if you have one.

The Travel in Traveling

Those who are experienced travelers undoubtedly have their tricks that they’ve learned when it comes to finding the best deals. Some of you might get lucky. Your new remote company might take care of booking the flight for you. If you need to book flights yourself, it’s recommended that you don’t wait until the last minute. Make sure you give yourself the proper amount of time to find a good deal and learn everything you can about the airline and the flight. What are their luggage guidelines and prices?

Preparation is the key element when traveling. Always ensure that you know your arrival time and try to work it so you arrive during the day if it’s a new place. Transportation is still easier to find during the day. If you can book your taxis ahead of time so they can meet you at the arrival gate, even better. Ask yourself what other transportation options are available to you. Always make sure you know how to get from the airport to your accommodation, as well. Consider downloading the map to your phone so you can follow along.

When you’re preparing for your trip, remember that not all airlines guarantee internet access on their flights. It’s possible that you can connect to meetings and emails while 30,000 feet in the air, but if there is no Wi-Fi during the flight, you’re at a loss. On the chance that you won’t be able to connect, ensure that you travel during a time where you won’t lose a day. Taking a vacation day or going on the weekend is recommended.

All Accommodations

Depending on how long you’re traveling for, your accommodations could change. If you’re staying for an extended period, like a few months, getting an apartment might be more economical. However, it’s suggested that you book a hotel, hostel, or even AirBnB first, and search for an apartment on arrival. Always ensure that you have an agent who can help narrow down apartment listings to suit you in safety, convenience, and budget.


Insurance is highly essential when you travel, and before you start traveling for the new company you are working for, asking questions about the protection they provide is crucial. Make sure that you read all of the fine print because you don’t want to be left responsible for thousands of dollars should something happen. If the trip is suddenly cancelled, is that covered by the company? If your electronics get stolen, does the company cover it? Do they provide you with health insurance?

Vaccinations and Medical

Depending on where you’re traveling, vaccinations might be a requirement, especially when traveling overseas. Continents such as South America and Africa require proof of vaccinations, whereas some others recommend it. You can typically investigate the vaccines needed by visiting a travel doctor or looking at the government’s health website.

If you have medical conditions that require you to take medications, ensure that you visit your doctor, so they can sign off on any bulk prescription fills. Also, confirm with the health insurance company that there aren’t restrictions.

Working for a company that allows you to travel is a lot of fun, but it can be a headache, especially if you have to sort out the travel specifics yourself. Talk to the company you are working for, ask them for their advice and ask them if anyone from the company has ever traveled to the place you’re visiting for them. The more information you have, the better. Your new position might be important to you and it’s likely that you want to do anything you can to impress them. Your safety is always more important.

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Working Remotely: How to Plan a Long-Term Trip

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