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?

Before you get lost in all the options, ask yourself: What do you actually want out of this adventure? Is it about soaking up a new culture? Finally visiting that dream destination? Or maybe just finding a place where the energy clicks and you feel at home?

Your first stop should be exciting and practical—somewhere that won’t blow your budget, has solid Wi-Fi, and helps you ease into the rhythm of nomad life without too much stress.

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 co-working spaces. Settling in should be easy. 

Here are a few beginner-friendly cities worth considering:

• Chiang Mai, Thailand – Calm, creative, and full of jungle energy. Great food, gentle pace, and an easy intro to Southeast Asia.
• Medellín, Colombia – Modern metro, eternal spring weather, and yes, the coffee lives up to the hype.
• Lisbon, Portugal – Sunshine, surf, sidewalk cafés, and those charming yellow tram cars weaving through the hills. You’ll come for the pasteis de nata and stay longer for the laid-back vibe.

• Oaxaca, Mexico – A slower pace, rich culture, and a city bursting with color—from handwoven textiles to street murals to vibrant markets. Artistic, earthy, and full of flavor.

• Bali, Indonesia – Wellness central with co-working spaces that look like jungle temples. Go for the views, stay for the smoothies.
• Barcelona, Spain – Beach city meets cosmopolitan buzz. You can work a few hours, then hit the sand or grab tapas in the Gothic Quarter.
• Cape Town, South Africa – Wild landscapes, fast internet, and a solid creative scene. Ocean on one side, mountains on the other.

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. Ease in.

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 a fish needs water—and it has 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. But things didn't go quite so smoothly.

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 you settle on a city, check co-working spaces, cafes, and internet quality on sites like TripAdvisor or Reddit. And yeah, ask the your Airbnb or hotel host to send a Wi-Fi speed screenshot—better to know before you hit "book."

3. Don’t Be a Time Zone Zombie

In Spring of 2014, when I went full nomad, I still had my heart set on Colombia. Warm weather, low cost of living, and amazing food made it seem perfect.  But I was thinking like a tourist—when I really needed to think like a nomad and a business owner.

At this point, I’d already built a remote team of writers, editors, and project managers to handle client work—most of them based in the Philippines. That 12- to 13-hour time difference was no joke. I was managing projects and putting out fires from my kitchen table in New York, often in the middle of the night, and it left me running on fumes. I knew if I didn’t get on the same schedule as my team soon, I’d turn into a full-on time zone zombie before I ever booked my first flight. That’s actually what tipped the scales for me—I chose the Philippines not just for its beaches and culture, but because it made my work-life flow easier.

When I landed in Lapu Lapu I was finally in the same time zone as my team, making communication much easier and freeing up my nights to sleep—or explore.  Time zone differences might sound minor, but they can make or break your experience. Every aspiring nomad should factor them in.

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 Barcelona 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 co-working 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, NY.

If I'd stuck with my NY budget, I could have lived luxuriously in the Lapu Lapu—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.

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 you’re picking your first destination. Things like language barriers, local customs, food, and even the climate can either make the experience feel exciting—or totally overwhelming.

To give you a general idea, here’s a rough “Culture Shock-o-Meter” based on what I and many other North Americans or Western travelers might feel:

• 1 (Mild): Portugal – Nomad-friendly, lots of English speakers, and plenty of Western comforts.

• 10 (Wild): Mongolia in winter – Remote, freezing, and full of unfamiliar routines.

Take Colombia, for example. On paper, it looked like the perfect intro to Latin America: colorful cities, rich culture, incredible nightlife, and not too far from the U.S. But once I started looking deeper, I realized English isn’t widely spoken—only about 4–5% of the population speaks it fluently. I’d been brushing up on Spanish, but I wasn’t confident enough to hold full conversations or really connect with locals right away.

The Philippines, on the other hand, felt way more approachable. Around 70% of Filipinos speak English, often fluently—and that made a huge difference. They were already helping me with client work, so I felt like I had a head start.

Later I learned that the Philippines used to be a U.S. colony. While the country has its own vibrant culture and identity, things like media, fashion, and even government systems felt surprisingly familiar.

I won’t lie—those first couple of weeks still felt like I’d landed on another planet. But I was having a blast and adjusted quicker than I expected.

So if you're just starting out, pick a place where the cultural learning curve won’t leave you totally wiped out. Either go where English is widely spoken, or somewhere you already know the language. You’ll settle in faster.

6. Nomad Hotspots vs. Hidden Gems

Bali and Chiang Mai get a lot of love—they’re remote work-friendly with fast Wi-Fi, co-working spaces, and built-in community. But some of the best spots aren’t on every top 10 list. They’ve got the charm, just without the crowds or the hype.

When deciding, ask yourself: do you want Bali’s co-working 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 

Climate is a huge factor. 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

Even in places that feel safe, certain neighborhoods can be sketchy, and situations can change overnight. Knowing the lay of the land helps: which areas are foreigner-friendly, what scams to look out for, and what (or who) to avoid.

Plenty of people live in Colombia for years in relative peace and love it, but they know the safe spots. For instance, Medellín neighborhoods like El Poblado and Laureles are great for expats, while areas like Comuna 13 can be risky if you’re not careful. Pickpocketing, dating app scams, and kidnappings are  not uncommon in certain areas.

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 co-working 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.

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?

Your first digital nomad spot doesn’t need to check every box—but it should make you happy. Maybe you’re chasing adventure, low cost of living, a better social life,  or just a place with good energy. Whatever your non-negotiables are, own them. Pick somewhere that makes it easy to get your work done and gives you something to look forward to when you close your laptop. That’s the whole point.

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.