How to Choose Your First Digital Nomad Destination (Without Overthinking It)

You’ve said goodbye to your 9-to-5, and now you’re dreaming of your first destination as a digital nomad. The world is wide open, but having numerous choices could feel overwhelming.

 Hmmm...where should you go first?

This is one of the fun parts of your new lifestyle, so take a deep breath and enjoy the process. The right choice balances adventure, practicality, and the main experience you're looking for on your trip. 

For my first nomad trip, I was convinced Colombia would be my destination—it had always been high on my travel bucket list. But when I started planning with a nomad’s mindset, I realized the Philippines was a better fit for me.

In this blog post, I’ll walk you through how I ultimately chose the Philippines and share the lessons I learned to help you pick a destination you’ll love.

1. Start Simple—The Goldilocks Principle

Your first digital nomad destination should feel just right—like a satisfying bowl of oatmeal, not too hot, not too cold. Choose a city with solid infrastructure: reliable transportation, abundant ATMs, well-maintained parks, and coworking spaces. Settling in should be relatively easy. Some destinations that fit the bill include:

• Chiang Mai, Thailand
• Medellin, Colombia
• Lisbon, Portugal
• Oaxaca, Mexico
• Bali, Indonesia 
• Barcelona, Spain
• Cape Town, South Africa

While it might be tempting to blaze your own trail, I recommend avoiding overly challenging destinations for your first outing. Hold off on the ayahuasca tour through the Amazon for now. You don’t want to dive into the ghost pepper of destinations when you can ease in with a mild, delicious Pad Thai.

Your first trip should be a winner, giving you confidence for bigger, bolder adventures later on.  

2. Follow Your Heart (And the Wi-Fi)

Wi-Fi is part of the infrastructure you should seek out, but it’s so critical it needs to be highlighted on its own. 

Nomads need Wi-Fi like we need water—and it needs to be fast. I learned this lesson the hard way as a newbie nomad during a trip to Puerto Princesa, Philippines, one of the most stunning tropical destinations in the world. I imagined spending my days hiking and kayaking, then catching up on work in the evenings.

Big mistake. 

The slow internet turned what should have been a quick 10-minute task—uploading image-heavy client reports—into a grueling 45-minute ordeal each night. Even a few extra seconds of waiting for files to load or messages to send can add up fast, stealing hours of your week—time that could be better spent exploring.

Before settling on a place to stay, research coworking spaces, cafes, and average Wi-Fi speeds. Before booking a hotel room or Airbnb, ask your host to send a screenshot of the WiFi speed to ensure it’s up to par.

3. Don’t Be a Time Zone Zombie

By August 2014, when I went full nomad and moved out of New York, I initially had my heart set on Colombia. Warm weather, low cost of living, and amazing food made it seem perfect. But here’s the thing—I had to be strategic. 

My outsourced team of writers was based in the Philippines, with a 12- to 13-hour time difference. Staying up all night to manage projects and troubleshoot issues left me drained and frustrated. I realized that if I didn’t address this, I’d burn out before my nomad journey even really began.

Relocating to the Philippines was as exciting as it was practical. Suddenly, I was in the same time zone as my team, making communication much easier and freeing up my nights for sleep or exploration. Every aspiring nomad should consider timezone challenges. 

Does your dream destination align with your work schedule? If not, you might end up a timezone zombie, staggering through meetings and missing out on the adventure you signed up for.

4. Decide: Budget vs. Bougie

Let’s talk money. Are you a $1 street taco kind of person, or would you rather rooftop sushi? Budget-friendly hubs like Medellín and Bali offer incredible value, while Lisbon and Tokyo lean on the pricier side. The key is knowing your style and what you’re willing to spend on comfort versus adventure.

When planning your first trip, research average costs for accommodations, food, and coworking spaces in potential destinations. Tools like Nomad List or Numbeo can give you a realistic sense of what to expect.

When I moved to the Philippines, I found a cozy beach bungalow in Lapu-Lapu with stunning ocean views for about a third of what I paid for my one-bedroom apartment in Queens.

If I’d stretched my Queens budget, I could have lived in pure luxury in the Philippines—think resort-style living or high-end condos. But I’m a simple guy. That ocean view felt like my own slice of paradise, and it reminded me that living well doesn’t always mean spending more.

Here’s the takeaway: Whether you’re budget-conscious or prefer the finer things, there’s a destination to match your travel style. Identify your non-negotiables, like location, comfort, or proximity to attractions, and prioritize your spending accordingly.

5. Consider the Culture Shock Factor

Your comfort zone matters when choosing your first destination. Language barriers, customs, and climate can enrich or overwhelm your experience. Here’s the “Culture Shock-o-Meter”:

• 1 (Mild): Bali – A nomad-friendly hub with Western conveniences.
• 10 (Wild): Mongolia in winter – Remote, freezing, and full of surprises.

Colombia initially seemed like a cultural jackpot: vibrant cities, rich traditions, and amazing nightlife, and relatively close proximity to the US. But as I dug deeper, I realized that most Colombians don't speak English (less than 5% of the population). Despite practicing Spanish, I wasn’t confident I’d speak it well enough to fit in right away. 

By contrast, about 70% of Filipinos speak English, many with high proficiency. After all, they were helping me write for my clients. That gave me confidence I’d settle in easily. 

I also later found out that The Philippines was once a US colony and while they have their own rich and distinct culture, many aspects—like language, government, media, and fashion—are heavily influenced by the U.S.

Although my first few weeks felt like I’d landed on another planet, I was having a great time and adapted surprisingly quickly.

Similarly, I suggest choosing a first destination where adapting to the local culture feels manageable or English is widely spoken—unless you already speak the local language.

6. Nomad Hotspots vs. Hidden Gems

Nomad hotspots like Bali and Chiang Mai are popular for a reason: they’re equipped for remote workers. But lesser-known gems can offer charm and authenticity without the crowds.

When deciding, ask yourself: do you want Bali’s coworking bliss or the charm of working from a café in the French countryside? Initially, Colombia’s active nightlife, beautiful beaches, and vibrant culture drew me in. But the Philippines stood out for its incredible diversity. With hotspots like Manila and Cebu City, it offered all the amenities a remote worker could need. 

At the same time, the country is home to hidden gems like Bantayan Island, Olango Island, Batanes, Siquijor, and Apo Island. The Philippines is an archipelagos with over 7000 islands.  You could live there your whole life and still not see everything. And knowing I’d feel welcome—socially and professionally—sealed the deal.

7. Chase the Weather (Unless You Love Freezing Fingers)

Climate can make or break your experience. Imagine sweating through Zoom calls in tropical humidity or shivering in an underheated apartment. Choose destinations that match your ideal weather vibes—sunny, mild, or comfortably cool.

Warm weather was non-negotiable for me. The Philippines’ sunny beaches and tropical breezes won me over. Plus, swimming alongside whale sharks—a dream ever since a diver in Belize told me about them—was the cherry on top.

8. Food Matters: Feed Your Soul and Your Stomach

Food isn’t just fuel—it’s part of the experience. Imagine indulging in fresh pasta in Italy or savoring spicy street food in Thailand. Your destination should cater to your taste buds as much as your wanderlust.

For me, culinary delights were a huge draw. Colombian arepas sounded amazing, but Filipino adobo quickly became a favorite. A place where food brings joy is always a win.

9. Put Safety First, Adventure Second

Safety is everything when picking a digital nomad destination. Even in places that feel safe, certain neighborhoods can be sketchy, and situations can change overnight. It’s all about knowing the lay of the land—what areas are good, what scams to watch out for, and who or what to avoid.

Take Colombia, for example. Plenty of people live there for years in relative peace and love it, but they know the safe spots. In Medellín, neighborhoods like El Poblado and Laureles are great for expats, while areas like Comuna 13 can be risky if you’re not careful. The same goes for Bogotá—Zona T is lively and secure, but some outer areas are better left alone.

Before you book that flight, do your homework. Look up crime rates, check out healthcare options, and read the latest travel advisories. A little research goes a long way in making sure you can enjoy your adventure without unnecessary stress.

10. Trust Your Gut: The One-Week Rule

Before committing to a destination long-term, spend a week there if you can. Think of it like a first date: it’s low commitment with the potential for something amazing. This short trial run lets you test the essentials—Wi-Fi speed, ease of getting around, and availability of coworking spaces—while giving you a chance to meet locals, soak in the atmosphere, and decide if it feels right for you.

When I finally made it to the Philippines, it didn’t take long to know I’d found a winner. Within days, I was captivated by the warmth of the locals, the stunning diving spots, and the growing digital nomad community. But beyond the obvious highlights, that trial week gave me insights I wouldn’t have gained otherwise. I discovered how easy it was to connect with people, manage daily life, and find reliable spots to work—all things that made it clear this was a place I could thrive.

Testing a destination gives you the freedom to explore without pressure. Maybe it’ll feel like home instantly, or maybe you’ll realize it’s not the right fit—and that’s okay. Either way, you’ll leave with valuable experience to guide your next choice.

11. Research the Visa Requirements

Whichever new country you land at, you’ll have to contend with visa requirement. Some countries make it easy with visa-free entry or visa-on-arrival policies, while others require more planning. For U.S. citizens, here are some common scenarios:

• Visa-Free Destinations: Countries like Mexico and several European nations in the Schengen Zone allow stays of up to 90 days without a visa.
• Visa-on-Arrival: Thailand offers a visa-on-arrival for U.S. citizens, but it’s limited to short stays. For longer terms, you’ll need to apply for a special visa, such as a tourist or nomad visa.
• Nomad Visas: Destinations like Estonia and Portugal offer dedicated digital nomad visas, allowing longer stays but requiring proof of income or remote work.
• Long-Term Options: The Philippines stands out as a unique choice. U.S. citizens can stay there for up to three consecutive years, provided they renew their tourist visa every two to six months. This flexibility means you can explore the country at your own pace without the anxiety of frequent relocations.

When I was deciding between Colombia and the Philippines, visas played a big role. Colombia’s 90-day visa policy felt restrictive compared to the Philippines, where I knew I could stay long-term and fully immerse myself in the culture. The ability to stay for years while renewing my visa periodically was a major draw, allowing me to explore the islands stress-free.

Where Will Your Journey Begin?

Choosing your first digital nomad destination doesn’t have to be perfect, but it should feel right for you. Whether you’re chasing fast Wi-Fi, affordability, safety, or a unique vibe, the goal is to find a place that makes it easy to work and adds a little spark to your day. Think about what you need to thrive and what excites you most—then start there.

Not sure where to start? Let’s figure it out together. Book a consultation with me, and I’ll help you pick the perfect spot.

I’ve been where you are, and I know what works—and what doesn’t. We’ll craft a plan that checks all your boxes and sets you up for an incredible first experience.

So, where will your adventure take you? Let’s make it unforgettable.