How to Work Remotely: Tips, Tricks & Job Ideas

By | Senior Writer
Last Updated: July 17, 2022
Working Remotely: Tips, Tricks & Job Ideas • Winetraveler

As so many professionals are now working from home, trends are emerging — like working remotely. Being a digital nomad certainly isn’t a new trend. But because so many more people are no longer required to be in the office, the options to live and work in the destination of your dreams (whether it be permanently or temporarily) could now become a reality.

Working remotely takes a little organization and planning. Here are some of the things you should consider if you want to give it a try.

Remote Job Ideas

Your job (and your internet access)

First of all, think about the job you have. Does your boss feel that working from home is the same as working remotely? Make sure changing destinations isn’t going to negatively affect your professional situation.

Once Covid-19 is no longer a threat, will you be required to be back in the office? Do you love working from home so much that you’d consider changing careers? If you’re not sure your job is ideal for long-term remote work, consider something new. The options are endless, but some of the most popular remote work careers are:

    • Web designer/developer
    • Freelance writer/editor
    • Social media marketer
    • Virtual teacher/tutor
    • Accountant
    • Consultant
    • Computer programmer
    • Virtual assistant
    • Translator
    • Travel agent


What’s the one thing that all these jobs have in common? Internet access. So wherever you go, make absolutely sure you have a strong Wi-Fi connection. It’s key to your success.

Remote Work Location Tips

Temporary or permanent?

If you plan to work remotely, it’s time to think about this decision in terms of time. Are you thinking two weeks, two months or two years? Is this just a few weeks of working remotely combined with vacation, or a serious lifestyle change, where you sell your home and hit the road?

Obviously, this choice is a big one, and it may depend on a number of factors: your age, your family, your belongings, commitments and community ties. You may not want to sell two homes and move your family of five to Malaysia, but working remotely in a mountain cabin for the summer a few hours from home may be more feasible. Likewise, if you’re young, single and renting, packing up and heading abroad indefinitely may be just the right remote work adventure.

RELATED: 11 Seriously Awesome U.S. Road Trips You Can Take Right Now

How To Work Remotely

Choose by destination

So once you’ve decided to work remotely, the next step is deciding where. Depending on your interests, you might prefer a secluded mountain cabin in Montana or a beach hideaway in the Caribbean. 

However, keep in mind that travel restrictions may cramp your style, as well as visa requirements. For example, at the time of writing, U.S. citizens aren’t allowed to enter the European Union, so don’t expect that snowy cabin to be in the Alps, or that sunny getaway to be in Marbella. Even once you can enter the European Union, U.S. citizens can only stay up to 90 days visa-free, so plan accordingly.

In fact, visas are another thing to consider, and that’s why the Caribbean may be a good choice for remote work, especially if you’d like to stay awhile. 

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 — they even have a special family bundle where you can bring your spouse and children. Antigua and Barbuda are offering a special ‘Digital Nomad Resident‘ program which offers a two-year visa to remote workers. 

Consider your budget

Another thing to consider is budget. Working remotely in Hong Kong or San Francisco is going to cost decidedly more than in Mexico or Colombia. But speaking of Mexico, this country is a valid option if you’re looking to work remotely for about six months. U.S. citizens can also currently enter Mexico and stay up to 180 days visa-free, and it’s definitely an affordable spot to live and work.

And don’t forget about the U.S., either. There are plenty of destinations close to home you can temporarily relocate to for winter sunshine, ski lifts, mountain hikes or just a general change of scenery. If you live in a big city, a country house may be just the medicine you need. If you’re surrounded by mountains, an escape to the beach could be refreshing. Those with families should opt for lots of outdoor space.

Things To Know About Working Remote

Hotel or home rental

The case for hotels

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.

One-off hotels in spots like the Nautilus Hotel in the Maldives are offering work remote packages too. The catch? These start at almost $24,000 per week.

While many hotels will likely offer more affordable remote work packages than those starting at $4,000 per night, generally, for a long-term stay, a home or apartment rental may be the best choice. 

The case for home rentals

Rental websites like Airbnb are now catering to those working remotely by offering one-month stay options directly on their homepage. And hosts are also tweaking their listings to ensure they’re apt for remote work, offering amenities such as a comfortable workspace, super-fast Wi-Fi, luxury coffee makers, bicycles, fully-equipped kitchens, laundry facilities and other things that may be appealing to working professionals.

And the longer your stay, the more a home rental makes sense. Being able to have a larger space than just a hotel room to call home for several weeks or months, the ability to do your own laundry and being able to cook your own meals will save you money and ensure you’re comfortable. After all, remote work isn’t always a vacation: it’s working while living elsewhere. Having access to the amenities you need to work efficiently and live comfortably are really important, especially for a long-term stay.


Your health is important, so make sure that wherever you plan to work remotely, you have access to healthcare. Covid-19 won’t just disappear in 2021, and it’s affecting destinations around the world. If you’re especially worried about it, make sure to consider the rules, regulations and Covid-19 policies in place at your destination. Stay informed about mask requirements and virus counts in your destination of choice, whether it’s the neighboring state or a new far-flung country.

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

For those leaving the country, make sure to understand all the health risks, not just coronavirus risks. Is Zika an issue? Malaria? Can you drink the tap water? Is there a hospital close by, and will your insurance cover you there? Doing the research will ensure you’re aware and prepared if any health situations should arise, Covid-19 or otherwise.

Bottom line

Working remotely seems exotic, and it can certainly be a wonderful way to cure your wanderlust while still growing professionally. Just do your research, and make sure to pick the right amount of time, the ideal destination and the perfect accommodation that fits the length of your trip, your budget and your family.

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One Comment

  1. For those that have been toying with the idea of remote working, I think now is as good a time as any to experiment with the option. Of course, this will be more applicable to some jobs than others, but I think there are ways to make it work.

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