Travel and Work Remotely: A Guide for 9-to-5 Professionals

The first time I seriously considered to travel and work remotely was back in 2014, when Remote Year was just gaining traction. I was working at a big tech company at the time, and the idea of traveling the world while keeping my job sounded exhilarating. I even had a long conversation with the person running their 12-month program, got super excited, and then… chickened out.

Fast forward to today, and oh, how times have changed! Remote work has gone from a niche lifestyle to a mainstream movement. The latest statistics estimate that over 9 million people regularly work and travel remotely, and that number keeps growing. With more companies embracing fully remote or hybrid models, international work visas tailored to digital nomads, and a surge in coworking-friendly accommodations, the barriers to working remotely while traveling are lower than ever.

Can 9-5 workers travel and work remotely?

Despite all the hype around the digital nomad lifestyle, one thing stands out: Most people sharing their experiences online are in creative fields – freelancers, content creators, designers, writers. They control their own schedules, choosing to work at 2 AM or take Wednesdays off if they feel like it. But what about those of us with full-time 9-to-5 jobs?

How do you balance remote work with back-to-back Zoom meetings? How do you navigate time zones without your boss side-eyeing your calendar? And, most importantly, how do you travel the world without compromising career growth?

That’s where we come in!

Why trust us with traveling and working remotely?

We’ve been fully employed in 9-to-5 jobs for the past three years while working remotely from across the globe. From the beaches of Hawaii to the heart of Europe, from safaris in Africa to remote islands in Australia, we’ve figured out how to make this lifestyle work—without skipping a beat in our careers. Promotions? We’ve scored them. Work efficiency? Never been higher. Travel experiences? Unforgettable.

The point is: You don’t have to quit your job, switch careers, or sacrifice financial security to live your dream life. And in this ultimate guide for high-earning 9-to-5 professionals, we’ll show you exactly how to do it. 🚀

Overcoming challenges in traveling and working remotely

Without further ado, let us jump into all the reasons you have given yourself to not partake in this dream life. Don’t get me wrong, it isn’t easy, but if you make it work like we did, there is no going back!

Time Zones

The first question everyone asks us is, “How do you handle the time zones?” After doing this for years, managing time differences has become second nature. The real trick, though, is choosing time zones that allow you to work sane hours while leaving plenty of time for travel and exploration.

For example, our work schedule is aligned with Pacific Time (Seattle/San Francisco/Vancouver). We choose our destinations to travel while working remotely based on the map above. Working from Europe is actually very comfortable for us—we spend our days sightseeing, then settle down to work from around 5 or 6 PM until 1 or 2 AM. On the flip side, working from places like New Zealand or Hawaii meant starting our day early at 6 AM, finishing up around 2 PM, and having the entire afternoon free to explore these incredible islands.

Wi-fi & Connectivity Issues

Good Wi-Fi is like oxygen when you work remotely—you don’t notice its importance until it’s gone. This is especially true when your days are packed with Teams or Zoom calls. Reliable connectivity becomes even more critical if, like us, you prefer working directly from your accommodation rather than finding coworking spaces, and especially if your work hours differ from local business hours.

After experiencing a few connectivity mishaps firsthand, we quickly learned how to avoid nasty surprises. We prioritize Airbnbs or Aparthotels over traditional hotels, partly due to internet reliability. A quick chat with our Airbnb hosts asking for an internet speed-test screenshot has now become standard procedure for us. Additionally, we always check reviews closely for any comments on Wi-Fi performance.

You can also reach out to hotels for internet information, though speeds can vary significantly depending on the room assigned to you. Still, if Airbnb isn’t an option, I’ve found Booking.com’s Wi-Fi ratings fairly reliable, particularly when there’s a common working area available. For instance, during a stay in Amsterdam, the DoubleTree hotel had unused conference rooms where I comfortably worked for a week at no extra cost—thanks to the convenient timezone difference!

Lastly, buying local SIM cards can be one of the best backup solutions, as data is relatively cheap in many countries. For example, while staying in Auckland, heavy rains flooded our building, knocking out the internet. We quickly grabbed a local SIM card offering 50 GB of data for NZD 100, which comfortably carried us through two days until service was restored.

Productivity & Career Growth

Work Ethic

If you genuinely enjoy your work, you’ll find yourself happily doing it anywhere in the world. Conversely, if your job isn’t something you look forward to, you’ll always find reasons to avoid it—no matter where you are. We’ve personally discovered that traveling and experiencing new cultures sparks our creativity and positively influences our productivity. Sure, there might be an occasional week where we put in 12+ hour workdays—but that’s manageable because we typically stay in each place for at least 3-4 weeks, ensuring stability and balance.

The Tech

Too many people have grown overly reliant on multiple screens. To many of you reading this (yes, I’m talking to you!), the thought of working without multiple monitors seems impossible. But we’re here to tell you that you don’t need to compromise. With innovative solutions like Xebec’s Tri-Screen or similar multi-screen portable attachments, you can easily recreate your comfortable workspace on the go. Adding a wireless keyboard and mouse to your travel kit is also hassle-free, making your mobile office as productive as your home setup.

Career Growth

Both of us have received multiple promotions while traveling and working remotely. We’re sharing this not to boast, but to emphasize that career progression and productivity aren’t compromised by remote travel. In fact, we’ve often found that new environments bring fresh energy and perspective, enhancing our overall performance.

Connections

One important thing to keep in mind as you grow in your career is that connections with others matter. We make it a priority to return home every few months and meet in-person with all the people we work with. This maintains that friendly rapport that is much easier to achieve in-person rather than on Zoom calls.

Note – This isn’t to say there won’t be a learning curve. You might need a trip or two to fully master the rhythm of balancing remote work and travel. But trust us—you’ll get there!

Visa Requirements

Navigating visa rules can seem overwhelming—I get it more than most. As someone who used to be an Indian citizen, I needed a visa to go practically anywhere. Becoming a Canadian citizen definitely eased things up, as we can now travel visa-free to Schengen countries, Australia, the UK, and about 170 other destinations. Most of these countries allow tourists to stay for at least 90 days, which is usually more than enough time (with the notable exception of the Schengen area).

However, don’t lose hope if you’re from a country with stricter visa requirements. There are countless examples of highly successful digital nomads from countries like India, who regularly secure visas and travel the world with ease.

The true game changers here are digital nomad visas. Countries like New Zealand, Portugal, Croatia, and Estonia now offer specialized visas tailored specifically for remote professionals. For shorter visits, standard tourist visas typically work just fine—but it’s crucial to confirm that remote work is permitted under these visas. Doing thorough research on each country’s requirements ahead of time has kept our travel experiences smooth, predictable, and stress-free.

Read our blog post on the new visitor visa changes by New Zealand which allows you to work remotely as a tourist. You can get your journey started as a digital nomad now!

Tax Considerations

Taxes can be complicated even when you’re not globe-trotting. We’ve simplified things significantly by following two simple rules: not staying in any single country for more than three months, and clearly maintaining Canada as our factual tax residence—regardless of where we find ourselves throughout the year.

We’ve come across people trying to avoid taxes by spending less than six months per year in their home country, but that’s illegal according to most countries’ tax codes. If you’re a 9-to-5 employee, your taxes are already deducted at the source by your employer. Attempting to dodge taxes is not only unethical—it’s a genuinely terrible idea.

It’s also essential to remember that from your employer’s perspective, prolonged work from abroad could trigger tax liabilities or compliance issues. Many companies have strict policies to avoid running into trouble with tax authorities, and others actively track how long employees are outside the country to manage risk.

Our recommendation? Always respect your company’s remote work policies and collaborate closely with an accountant who specializes in remote work and expat taxation. This way, you can enjoy your remote lifestyle without unwelcome tax surprises.

Health Insurance

Reliable international health insurance tailored specifically for remote workers—such as SafetyWing or World Nomads—is our go-to solution. Personally, I’ve always preferred SafetyWing, but the best choice ultimately depends on your traveling style and the types of activities you plan to do.

Always double-check the details of your insurance coverage, especially concerning emergency medical care and repatriation. Knowing exactly what’s covered ensures peace of mind, so you’re confidently protected wherever your travels take you.

Many big tech companies offer some form of out-of-country health coverage, sometimes extending up to 30 days. While generous, we strongly recommend against relying solely on this employer-provided insurance, as it can trigger unintended complications or policy violations at your workplace. Always have your own dedicated travel health insurance plan as a backup.

Managing Finances

One of the most important considerations when traveling long-term is managing your finances effectively. Even if we’re talking about high-earning individuals here, money doesn’t grow on trees—being smart about expenses is crucial.

For instance, do you have a mortgage back home? Paying for hotels or Airbnbs while also managing your mortgage payments can quickly become expensive. We typically rent out our place to cover our monthly mortgage payments. House hacking, if possible, is another fantastic way to cover your travel expenses entirely or at least substantially reduce them.

Do you have car payments? Consider renting out your vehicle on Turo to offset this expense. Utilities? Don’t forget to turn down your hot water tank and adjust thermostats before you leave—a small action that saves significant money over time.

Most importantly: travel credit cards! Oh, I can talk for days about these. If you’re a U.S. resident (or even have an SSN from a previous stay in the U.S.), you’re essentially sitting on a pot of gold. There are endless credit cards with amazing welcome bonuses you can leverage for travel. Plus, using travel-oriented credit cards like the Chase Sapphire Reserve or Capital One Venture X for everyday expenses allows you to rack up points rapidly.

Lastly, we recommend diligently tracking your monthly expenses. Whether through a fancy app like Rocket Money or just good old-fashioned Excel spreadsheets, monitoring your spending helps you understand your habits, categorize expenses clearly, and adjust accordingly as you move forward.

Eating Healthy

While healthy eating might not be at the top of your priority list, it definitely ranks high on ours! When you travel and work remotely for the majority of the year, you’ll quickly realize that constantly eating out isn’t healthy, or budget-friendly. This is yet another compelling reason we prefer Airbnbs or hotel rooms with full kitchens (not kitchenettes! big difference!).

Our tried-and-true method involves first locating the nearest supermarket to our Airbnb and stocking up on all the essentials we need to cook wholesome meals. Additionally, we travel with a small set of essential spices and utensils that we know aren’t always readily available in Airbnb kitchens. Cooking our own meals helps us feel much more at home, even when we’re far from it, and allows us to reserve dining out for places we genuinely look forward to experiencing.

Exercising & Staying Healthy

Whether we’re at home or traveling, we always try to prioritize our health by exercising as often as possible. We understand that everyone has different requirements and levels of exercise, so here are some suggestions based on what works for different people.

For those looking for light to medium intensity workouts, we recommend 21-day yoga challenges or calisthenics routines. These usually take about 30 minutes a day and can easily be done right in your accommodation, whenever your schedule allows. If you’re someone who enjoys running, traveling is perfect, since every new place gives you a fresh set of surroundings to run in, which keeps it fun and motivating.

For those needing a heavier workout routine that involves gym time, your options will depend on where you’re traveling. In countries like the US or Canada, something like ClassPass works really well to get access to open gym time in a flexible way. In many countries (Australia, the UK, Canada, US, etc.), there are nationwide chains of low-cost gyms where you can get a one-time membership and access multiple locations as you travel.

And if none of these options are available, I’ve often just walked into a nearby gym and asked about a weekly or monthly pass—or even passes for a set number of days. As long as you ask nicely, in my experience, most gym managers are more than happy to find something that works for you!

Looking to stay fit while traveling? Read our complete guide on budget gyms around the world and at-home workouts tips! 

Mental Health and Loneliness

It happens, and we get it. Even though we travel and work remotely as a couple and are quite content in our little bubble, we know that many of you draw energy from being around others and crave more social interaction.

If that sounds like you, we recommend joining organized tours, local meetups, or group classes at gyms or studios. These can be great, low-pressure ways to meet like-minded people. Bars with trivia nights, karaoke, or live music also tend to be more social and open to conversation, especially if you’re traveling solo. We also frequently end up making new friends as we travel. Look at our new besties from our Antarctica trip!

And don’t underestimate the power of staying connected with your own circle. We make it a point to call friends and family regularly, often with long chats that ground us and make us feel more in touch with our world—no matter where we are.

Kids

Yes, we left the toughest one for the end. We personally do not have experience traveling with kids (or even having them!). But we see a lot of folks traveling with their kids. From what we gather, these people have chosen to home school their kids part-time or full-time. If you really want to travel the world, and are open to home-schooling your kid, it might be an excellent way to raise your kid with a broadened horizon and cultural sensitivity and knowledge. Give it a thought!

How to choose the right destination to travel and work remotely

Choosing the right place to travel to and work remotely isn’t as simple as picking the most Instagrammable destination. There are a few practical things we always consider before deciding on a place. And over time, it’s become a bit of a ritual for us.

Step 1

Start by figuring out how much time you have for this trip. Are you planning to be away for a couple of weeks, a month, or longer? This is super important because your stay duration will directly influence how much you can see and how fast you need to move. Our personal rule? We stay a minimum of 2–3 weeks anywhere. We’ve learned the hard way that lugging suitcases around every few days gets old really fast—and it starts eating into your energy, your routine, and eventually, your productivity. Go slow to go fast. That’s the mindset that’s worked best for us.

Step 2

Next, figure out which countries are high on your list, and more importantly, whether it’s the right season to visit them. If your top destination is in the middle of a rainy season or unbearably hot, maybe it’s worth pushing it down the list and picking a better alternative for now.

Step 3

Once you know your timeframe and your potential destinations, consider what your work schedule looks like. If you’re working 9 to 5 Pacific Time (like we do), time zone compatibility becomes a real factor. Not all countries are easy to work from if you’re logging on at 2 a.m. local time. So ask yourself: is this destination practical for the hours you’ll be working?

Also, don’t go in with the mindset that you’ll be out exploring every single day. That’s a fast track to burnout. Instead, aim to enjoy the region more like a local. We plan to go out twice or maybe three times during weekdays, and then use weekends for day trips or exploring deeper. This is why longer stays feel more grounded. You can keep up your work rhythm without feeling like you’re missing out.

Step 4

Once you’ve shortlisted your destination, it’s time to check flights. We love using the “Explore” option on Google Flights as it gives you a broader view of what’s affordable around your desired region. Sometimes, flying into a nearby airport instead of your final destination, then hopping onto an ultra low-cost carrier (like Ryanair in Europe or Jetstar in Australia) can save a ton of money.

Step 5

After that, move on to accommodation, and this one’s critical. If you’re working full-time, the place you stay will directly impact your day-to-day experience. We always check for reliable Wi-Fi, and we’ll often reach out to the host or hotel for a speed test screenshot. If you’re someone who thrives in coworking cafés or open lounges, and your timezone makes that doable, you can factor that in too. But in general, we prefer places that give us the option to work from home comfortably.

Pro tip: filter pricing properly on sites like Airbnb. You’d be surprised how many affordable places get buried unless you manually lower the price range slider. And don’t forget to compare with local aparthotels or even booking.com—sometimes, they have better deals or amenities more suited to remote work.

So in short, choose your destination based on the season, your priorities, how long you’ll stay, cost to get there, and cost to live there. The right place isn’t always the most famous one—it’s the one that supports your lifestyle while letting you soak in a new culture without stress.

Take your time. Go slow. Let the place feel like home. That’s where the magic is.

Why Travel and Remote Work Go Hand-in-Hand

The biggest win of working remotely while traveling is simple: you don’t have to pause your life to explore the world.

You can stay financially secure, keep growing in your career, and still wake up in a new city every few weeks. For us, this lifestyle has sparked more creativity, brought more balance into our routines, and helped us live more intentionally. Travel breaks up the monotony of daily work life, while work gives structure and purpose to each day—so the two actually complement each other really well.

It also helps you become more adaptable, better at time management, and a lot more resourceful. And honestly, few things beat finishing a day of meetings and stepping out to watch the sunset in a place you’ve never been before.

How do I get started?

If you’re new to this whole travel and work remotely lifestyle, don’t worry, we’ve got you, my friend. By the time you’ve read through this entire post, the only thing left to do is find a little courage to take that first step. After that? Trust us, the world will do the rest. Once you’re out there, the motivation comes naturally.

Our suggestion? Start small. Pick a destination where you can stay for 2 to 3 weeks. If flights are pricey, choose something closer to home. We started with Chicago, for example—a city that was perfect for testing the waters. We’d start the day with a morning coffee by the emerald-green river, work through our usual 9-to-5, then head out in the evenings to explore the bar and restaurant scene. Simple, easy, and so rewarding.

Also, don’t plan your first trip during a peak work period. If your first experience involves 12-hour days glued to your laptop, you’ll barely see the place you traveled to. And then you’ll feel guilty for “wasting” the trip. That’s not the feeling you want to associate with this lifestyle. Give yourself space to enjoy the destination.

And finally, stay flexible. Things won’t always go to plan—Wi-Fi may go down, time zones might be tricky, or your favorite café may be closed for renovations. Roll with it. Flexibility is the superpower of traveling and working remotely.

Start small, stay open, and let the world show you how good this can get.

Frequently Asked Questions (FAQs)

What kind of internet speed is enough for remote work?

For most people in meetings all day (Zoom, Teams, Slack), a minimum of 20 Mbps download / 5 Mbps upload works fine. (I’ve used 5-10 Mbps as well in some places, and it seemed to be ok) But if you’re on video calls with multiple people, sharing large files, or working in cloud environments, aim for 50+ Mbps download and 10+ Mbps upload. Always ask for a speed test screenshot from your host or check reviews, don’t trust the listing alone.

How can I keep my location private while working remotely?

If you’d rather not share your exact location with your employer as you travel and work remotely, use tools like a VPN to mask your IP address. An additional layer of security we use is to have a VPN-enabled router, like GL iNet, and then connect our laptops to that. Also, avoid casual giveaways—like local time references or check-ins on public Slack channels. That said, make sure you’re still aligned with your company’s remote work policy if you’re going international.

Are there Airbnb filters that help ensure a better remote work setup?

Yes! Look for listings with Dedicated workspace (Airbnb’s filter)

Can remote work cause depression?

No! Not if you manage it properly. Make sure you travel slow, keep your social connections going and keep a close track of your finances. That’s all you need to stay happy!

Where do I find remote work jobs?

There is no dearth of remote work jobs that can allow you to travel and work remotely, even if all you hear about is return-to-office (RTO). Look at forums like FlexJobs, LinkedIn, WorkingNomads or WeWorkRemotely for an incredible number of options.

What should I consider with check-in and check-out times for work trips?

Check-in at 3 PM and check-out at 10 AM doesn’t mix well with back-to-back meetings. Depending on what time we are working, we keep an open mind about which days to travel on. In Europe, it is easy to travel on any day of the week, as long as we are checked-in by 5 PM to start working. In places like New York or South America, we usually check-out/in on weekends since our work timing would leave us without a workspace otherwise.

What gear should I always carry for working remotely?

We never travel without:

• A universal travel adapter
• Noise-canceling headphones
• A wireless mouse
• Optional: portable second screen (Xebec or similar) if you’re used to multi-monitor setups

How do I handle work calls in tiny or noisy accommodations?

It happens! Our go-tos:

• Use noise-canceling headphones with a mic
• Sit near a wall to reduce echo if you’re in a bare space
• Have a virtual background ready in Zoom
• If things get rough, we’ve even done calls from parked rental cars or stairwells (not glamorous, but effective)

Check out our blog post on the top destinations to work remotely and travel from!

Final Thoughts

At the end of the day, this lifestyle isn’t about quitting your job, chasing Wi-Fi across beaches, or stuffing your calendar with bucket list items. It’s about designing a life that lets you grow professionally while staying curious about the world.

You don’t need to be a digital nomad or an influencer. You just need to take that first step – thoughtfully, intentionally. And trust that the rest will unfold. If we’ve learned one thing over the past few years, it’s this: you don’t have to choose between career and adventure. You can have both.

So go ahead. Pick a place. Block your calendar. And start imagining what work-life balance could really look like when the whole world becomes your backdrop.

We’re rooting for you. 🌍💻✈️