The 7 Bucketlist Destinations of My Digital Nomad Dreams

After more than 10 years of the grind, I finally have some time on my hands. What now?

That's the question on my mind lately. Our headhunting agency, Support Shepherd, is growing fast! We're close to hiring 2,000 remote workers from the Philippines, and we've recently brought on a COO based in the US. Suddenly, my schedule has opened up, and my to-do list has some wiggle room. What's next on my adventure?

Thanks to the wonders of remote work, life has turned into a non-stop journey. I'm excited to announce that it's finally time for me to embark on a personal quest that combines my passion for work with my love for exploration.

Beyond building my own business, there's always been a desire to see the world beyond the office walls.

As someone who firmly believes in the magic of work-life harmony and the "pura vida" philosophy, I want to share with you the seven must-visit destinations that are fueling my digital nomad dreams.


How the World is Opening up for Digital Nomads

The working world has had quite the makeover recently. The traditional office isn't the only place where business magic happens anymore.

With the rise of cool co-working spots, internet connections that don't quit, and a worldwide community of kindred spirits, the entire planet has transformed into our playground. Being a digital nomad isn't just about clocking in from faraway places. It's about the adventures and friendships we create along the way.

While I've roamed through various nooks and crannies of the Philippines and Southeast Asia, it's high time to spread my wings a bit further.

My Digital Nomad Bucketlist

With tech wizardry making remote work a breeze and more folks jumping on the virtual work bandwagon, it's time to unleash my inner explorer. If I could wave a wand and start my journey, here's where I'd kick things off.



1. United States: Where BBQ Meets Business

My first stop on this wild ride is the good ol' United States.

It's a big deal because it's my maiden voyage to the land of the brave and the free. Plus, it's a golden opportunity to reunite with Marshall, my co-founder, who's been holding down the fort in Texas. We've been tight online, but nothing beats a face-to-face chat for taking things up a notch in the business world.

Why it's great for digital nomads:

The US is a hub for all things innovative, which makes it a goldmine for digital nomads. There are endless chances to network, collaborate, and dive into exciting work adventures. With co-working spaces galore and a startup scene that's sizzling, it's a dream come true for remote-working wanderers.

The cultural hotpot here is a blast. From the entrepreneurial buzz of Silicon Valley to the work-hard-play-hard vibe, it's all in sync with my mantra of finding the sweet spot between hustling and having a blast.

When I'm not punching the digital clock, here's what I've got on my to-do list:

  • Soak in the live music scene and munch on mouthwatering BBQ in Austin.

  • Take a gastronomic tour from Tex-Mex tacos to finger-lickin' barbecue delights.

  • Stand in awe at the Grand Canyon, one of Mother Nature's finest creations.


2. Iceland: Chasing Dreams and Northern Lights

Iceland, with its fire and ice landscapes, has always been my dream.

Why it's great for digital nomads:

Iceland's tiny population and solid internet setup are a digital nomad's dream come true. Plus, those jaw-dropping views from your window are sure to kick your productivity into high gear.

Iceland's "pura vida" vibes hit close to home. It's all about savoring the moment and finding joy in the simple things – a philosophy that jives perfectly with my work-life harmony mantra.

When the work cap comes off, here's what's on the menu:

  • Catch the electrifying Northern Lights show during the winter months.

  • Tour the Golden Circle, where otherworldly landscapes await your exploration.

  • Take a dip in the famous Blue Lagoon for some serious rejuvenation.

3. Lisbon, Portugal: Old World Charm with a Nomad Twist

Lisbon, the capital of Portugal, is a charming city that effortlessly blends history, culture, and modernity. That’s my next stop.

Why it's great for digital nomads:

Lisbon knows how to roll out the welcome mat for remote workers. It's budget-friendly, the expat community is all smiles, and the weather's just right. Cozy coffee shops and co-working spaces are a dime a dozen, making it a work-play paradise.

The Portuguese have a knack for family, community, and finding joy in life's little pleasures. Sounds a lot like my work-life harmony vibe.


When the laptop's closed, here's my Lisbon agenda:

  • Wander through the charming Alfama neighborhood, where history oozes from every corner.

  • Dive face-first into Portuguese pastries like Pastéis de Nata.

  • Let the soulful tunes of Fado music transport me to a different world.

4. Japan: Tech and Tranquility

Japan is a country of contrasts, where ancient traditions coexist with cutting-edge technology. This jaw-dropping dance has always fascinated me, making it a top destination on my bucketlist.

Why it's great for digital nomads:

Japan delivers the digital goods with speedy internet, efficient trains, and a tech-loving culture. It's a haven for nomads who crave reliability and high-tech efficiency.

Japanese culture is all about discipline, precision, and respect, qualities that sync up with my work ethics. But don't let that fool you; they know how to kick back and enjoy life – a must for my work-life harmony vision.

When the screen dims, here's my Japan wish list:

  • Get zen in Kyoto's serene temples and gardens.

  • Dive into the bustling metropolis of Tokyo, where tradition and innovation shake hands.

  • Sample everything from sushi to ramen and savor the flavors of Japan.

5. Greece: Island-Hopping, Ouzo Sipping

Greece has been calling my name for as long as I can remember. With its rich history and stunning Mediterranean landscapes, Greece has always captured my imagination.

Why it's great for digital nomads:

Greece checks all the boxes – stunning views, affordability, and locals who are all about the warm welcome. The Mediterranean vibe and the laid-back lifestyle create the perfect backdrop for work and play.

Greek also culture revolves around "kefi," the joy of life's simple pleasures. That's my kind of philosophy.

When the keyboard goes quiet, here's what's on the Greek agenda:

  • Explore the ancient wonders of Athens, including the legendary Acropolis.

  • Island-hop through the Cyclades, savoring the beauty of island life.

  • Dive into fresh Mediterranean cuisine with the sparkling sea as your backdrop.

6. Switzerland: The Ultimate Office with a View

With its pristine landscapes and reputation for clockwork efficiency, Switzerland a destination that embodies the perfect blend of work and leisure.

Why it's great for digital nomads:

Switzerland has got the remote work game locked down. Solid infrastructure, reliable internet, and efficient public transportation make it a digital nomad's dream. The awe-inspiring natural beauty doesn't hurt either.

The Swiss are all about discipline, precision, and punctuality – values that sit well with my dedication to excellence. But they also know how to kick back and enjoy the finer things in life.

When I'm not on the clock, here's what I've got in store:

  • Take a train ride through the Swiss Alps for views that belong in dreams.

  • Explore the charming cities of Zurich, Geneva, and Lucerne, each with its unique charm.

  • Dive into Swiss chocolate and cheese – a culinary adventure that complements the breathtaking landscapes.


7. Canada: Balancing Work and Wilderness 

Last but not least, Canada. Where wilderness meets warm-hearted locals, it’s a place that has long beckoned to my adventurous spirit.

Why it's great for digital nomads:

Canada is all about safety, quality of life, and a friendly atmosphere. It's got the infrastructure digital nomads dream of, with co-working spaces and innovation hubs galore. And the breathtaking natural beauty is the icing on the cake.

Canadian culture is all about diversity, inclusivity, and finding the perfect balance between work and life. Sounds a lot like my work-life harmony dream.

When the laptop's stashed away, here's what's on my Canadian checklist:

  • Lose myself in the stunning Banff National Park, nestled in the Canadian Rockies.

  • Dive into the multicultural vibes of cities like Toronto and Vancouver.

  • Immerse in the unique French-Canadian culture of Quebec.

Ready to tick off your bucketlist?

Excitement is bubbling up as I gear up for this incredible journey through my digital nomad bucketlist, I can't help but feel the excitement bubbling up.

When these destinations promise a unique blend of work opportunities, cultural immersion, and natural beauty that aligns perfectly with my values of work-life harmony and the "pura vida" philosophy — is any one really to blame?

But enough about me! What about your digital nomad dreams?

Whether you're a newbie or a remote work master, I hope you get to explore the world with open arms, just as I am doing now. 

Ready to learn and grow together as we redefine the way we work and live? The world is waiting!

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