There’s a funny thing about buying property abroad: the moment people start dreaming about it, they immediately picture the capital city. Parisian balconies, Lisbon’s tiled facades, Bogotá’s mountain views, Bangkok’s neon skyline.

The capital is shiny. It’s famous. It’s the first place you’ll see on Instagram when someone says “I’m moving abroad.”

But if you’re a digital nomad—or even a remote worker planning your first long-term base—the capital is often the wrong place to put your money.

And I say this as someone who loves capital cities. But when it comes to buying strategically, building passive income, and creating a lifestyle that actually works… the real gems are often hiding in the second cities, creative hubs, and overlooked regional capitals.

Today, let’s talk about the underdogs—the cities that quietly outperform their glamorous national counterparts when it comes to ROI, livability, rental demand, and long-term potential.

Before we hop around the world, let’s clarify what we’re looking for. A good digital-nomad-friendly investment isn’t just about low prices. It’s about:

Capitals might have more prestige, but second cities usually have more value, flexibility, and room to grow.

Now, let’s break down the real MVPs around the world.

Why Not Lisbon:
Lisbon is stunning, but with skyrocketing prices, housing shortages, and highly restricted short-term rental licenses, buying there has gone from “smart move” to “good luck.”

Why Porto Wins:

Best Rental Strategy:
Furnished long-term rentals, student flats, or remote-worker housing. Fantastic yields outside the historic center.

Why Not Mexico City:
Mexico City is magical—but it’s also a monster: chaotic, dense, and increasingly expensive. Rental competition is fierce.

Why Oaxaca Wins:

Best Rental Strategy:
Short- and mid-term rentals for tourists, artists, and backpackers. Many colonial homes convert beautifully into small guesthouses.

Why Not Bogotá:
Bogotá is high-altitude, chilly, traffic-heavy, and increasingly strict with rental zoning.

Why Medellín Wins:

Best Rental Strategy:
Boutique short-term rentals in tourist-friendly areas like El Poblado or Laureles, or mid-term units for nomads.

Why Not Kuala Lumpur:
KL has big-city energy, but it can feel corporate and overwhelming—great for business travelers, not always great for nomads.

Why Penang Wins:

Best Rental Strategy:
Long-stay rentals for retirees, medical travelers, and remote workers.

Why Not Bangkok:
Bangkok is electrifying, but the pace is intense, condos are pricier, and local rules can be tighter.

Why Chiang Mai Wins:

Best Rental Strategy:
Mid-term stays (3–6 months) for remote workers, artists, and wellness travelers.

Why Not Tbilisi:
Tbilisi is fantastic for culture and cuisine, but Batumi is the better buy right now.

Why Batumi Wins:

Best Rental Strategy:
Airbnb in summer, student and nomad rentals the rest of the year.

Let’s zoom out and look at the trends.

You’re not fighting hedge funds or giant developers.

Small and mid-sized cities tend to offer easier rental licensing and fewer bureaucratic headaches.

The capital may already be overvalued; the second city is still climbing.

Everything is calmer, cheaper, friendlier, and just… more livable.

As a nomad, you’re designing your life around comfort, freedom, and mobility. Second cities often offer all of that, plus the chance to buy before everyone else discovers them.

No market is perfect. Watch out for:

None of these are deal-breakers, but they’re important to factor into your strategy.

Forget prestige. Forget capital glamour. Forget the skyline on the postcard.

Ask yourself one question:

That’s the city your future tenants want too.
And that’s where your investment grows.

Second cities aren’t second-rate—they’re often the smartest move in an overpriced world.