The world’s best cities, ranked

🌍 Top 20 Best Cities in the World

1. Tokyo

Hypermodern yet deeply traditional. Food paradise, neon nights, quiet shrines, cutting-edge fashion, and the most efficient transit on earth.

2. Paris

Unrivaled for art, food, style, and sheer beauty. A city where life feels like theater, and even the everyday is elegant.

3. New York City

The ultimate city of ambition and reinvention. Intensity, diversity, and energy unmatched anywhere else.

4. Barcelona

Dreamlike architecture, Mediterranean beaches, and a cosmopolitan lifestyle — all with Gaudí’s surreal flair in the background.

5. London

Historic grandeur mixed with constant reinvention. Theater, museums, pubs, parks, and neighborhoods that feel like their own worlds.

6. Istanbul

Where East meets West, literally. Byzantine domes, Ottoman mosques, buzzing bazaars, and a rich cultural layering unlike anywhere else.

7. Rome

An open-air museum with astonishing history, yet still a living, chaotic, passionate city.

8. Berlin

Countercultural energy, thriving art and music, gritty cool. A city defined by reinvention and creative freedom.

9. Hong Kong

Vertical, cinematic, neon-soaked. World-class food and harbor views — a Blade Runner-esque metropolis with a strong cultural identity.

10. Lisbon

Pastel-colored hillsides, soulful fado music, trams climbing cobbled streets, Atlantic breezes — effortlessly charming.

11. Mexico City

Explosive creativity, ancient ruins, vibrant neighborhoods, and one of the best food scenes on the planet.

12. Sydney

Harbor, beaches, surfing, and an outdoors lifestyle paired with cosmopolitan dining and arts.

13. Buenos Aires

European elegance meets Latin American passion. Tango, steak, cafés, bookstores, and nightlife that goes until dawn.

14. Copenhagen

Scandinavian design perfection, canals, bikes, Michelin-starred dining, and a sense of hygge (coziness) in daily life.

15. Rio de Janeiro

Dramatic natural beauty — mountains, beaches, rainforest — paired with infectious music, dance, and carnival energy.

16. Marrakech

A city of colors, scents, and textures. Labyrinthine souks, Moorish architecture, rooftop riads — sensory overload in the best way.

17. San Francisco

Golden Gate vistas, countercultural history, tech-driven present, and a breathtaking natural setting.

18. Seoul

24/7 dynamism, from cutting-edge K-culture to serene palaces. Food, shopping, and nightlife on a global scale.

19. Cape Town

Where mountains meet ocean. Extraordinary natural beauty, vineyards, wildlife, and a cosmopolitan cultural mix.

20. Amsterdam

Canals, bikes, liberal spirit, intimate charm, and a global cultural footprint far bigger than its size.

👉 If you want, I can also break these into best for living vs best for visiting — since a city like New York or Tokyo might be exhilarating to visit but overwhelming to live in, while Copenhagen or Lisbon might hit the sweet spot for daily life. Would you like me to do that comparison?

Got it — let’s re-rank these cities with “living there as a North American” in mind. That means weighing:

• 🌍 Cultural excitement (still matters — you want stimulation).
• 🏡 Quality of life (safety, healthcare, walkability, green space, pollution).
• 💬 Language barrier (how workable English is day to day).
• ✈️ Connectivity & lifestyle compatibility (ease of travel, time zones, cultural fit).
• 💸 Cost of living (especially compared to NYC/SF).
• 🤝 Social ease (friendliness, openness to expats).

Here’s a re-ranked Top 20 Cities in the World to Live In (as a North American):

🏆 Top 20 Cities to Live In (as a North American)

1. Copenhagen

Effortlessly livable: safe, clean, bike-first, design-forward, English widely spoken, social welfare strong. Expensive, but an easy fit for North Americans.

2. Amsterdam

Compact, bikeable, very international. Nearly everyone speaks English. Liberal, open-minded, and easy to integrate.

3. Lisbon

Beautiful, relaxed, sunny, affordable (by Western Europe standards). Welcoming to expats, thriving creative scene, and English is common in younger circles.

4. Barcelona

Mediterranean lifestyle with cosmopolitan energy. Sun, food, culture. English not universal, but very liveable once you adjust.

5. London

Global hub with endless stimulation. No language barrier. Downsides: weather, expense, and intensity.

6. Berlin

Affordable (still, compared to Paris/London), open, progressive, and English-friendly. Creative scene thrives. Bureaucracy can be a headache, but expats love it.

7. Paris

Romantic and culturally unmatched. Harder bureaucracy, language barrier unless you speak French, but if you do — extraordinary.

8. Sydney

English-speaking, outdoorsy, warm-weather city with beaches + global culture. Far from North America, but lifestyle payoff is huge.

9. Tokyo

Utterly thrilling. Safe, clean, efficient. Language and cultural integration more challenging, but many North Americans fall in love.

10. Stockholm

Design, safety, equality, nature access. English fluency high. Expensive, winters long, but quality of life stellar.

11. Toronto

Closer to home, highly multicultural, globally connected. High cost of living, but easy cultural fit.

12. Mexico City

Vibrant and creative, affordable, warm climate. Large expat communities. Downsides: safety concerns, air quality, traffic.

13. Buenos Aires

Affordable, lively, deeply cultural. English less common, bureaucracy tricky, but lifestyle is rich and welcoming.

14. Vancouver

Nature + cosmopolitan. Mountains, ocean, multiculturalism, clean and safe. Expensive, rainy, but a dream for outdoorsy types.

15. Rome

Glorious history and food culture. More chaotic daily life (bureaucracy, infrastructure), but endlessly rewarding if you lean into it.

16. Seoul

Exciting, tech-forward, safe. Language barrier is real, but there’s a thriving international community.

17. Vienna

Orderly, elegant, and consistently rated high for quality of life. English not universal, but integration possible.

18. Madrid

Warm, lively, more relaxed than Barcelona. Affordable for a European capital. English less common, but lifestyle very appealing.

19. Montreal

Bilingual, cultural, vibrant. Easier as a North American to settle in, though winters are intense.

20. Cape Town

Stunning scenery, outdoors lifestyle, affordability. Downsides: safety concerns and inequality — but culturally and naturally extraordinary.

Perfect question. Lisbon is one of those cities that has exploded in popularity among North American expats in the last decade — and for good reason. Let me break it down with an eye toward why you or Stephen might find it appealing.

🌆 Lisbon as a Place to Live

1. Everyday Atmosphere

Lisbon is visually charming and emotionally uplifting. Pastel-colored houses, tiled facades, steep cobblestone streets with yellow trams climbing them, sunlight glinting off the Tagus River. Unlike many big capitals, it doesn’t feel overwhelming — there’s a gentleness to the pace of life.

It has a neighborhood feel — alfama with its winding alleys, Bairro Alto with nightlife and music, Chiado for cafés and culture, and riverside areas that feel open and airy.

2. Weather & Natural Setting

Lisbon enjoys one of the best climates in Europe:

• ~300 days of sunshine a year ☀️
• Winters are mild (light jackets, not heavy coats).
• Summers are hot but breezy thanks to the Atlantic.

You’re right by stunning beaches (Cascais, Costa da Caparica) and surf towns like Ericeira. Day trips to Sintra’s palaces or hikes along the coast are easy.

3. Cost of Living

Compared to New York, SF, London, or Paris, Lisbon is affordable — though rising fast due to demand.

• Rents are still cheaper than other Western capitals (though locals feel the crunch).
• Eating out is inexpensive and delicious: fresh seafood, pastries, wine.
• Healthcare is solid and far cheaper than the U.S.

4. Cultural Fit for North Americans

• English widely spoken, especially among younger people, so you won’t feel locked out.
• Welcoming expat community — lots of creative professionals, tech workers, digital nomads, writers. You’d find kindred spirits quickly.
• Lifestyle: people enjoy long café hangs, late dinners, weekend beach trips. It’s social and easygoing.

5. Why You (Jay) Might Like It

• Romantic, atmospheric, and photogenic — incredible for your photography.
• Literary vibe: historic cafés, writers who adored it (Pessoa, Saramago).
• A culture of conversation, music (fado), and philosophy that meshes with your intellectual + creative side.
• Perfect base for your writing + AI teaching work: international enough to keep you stimulated, affordable enough to give you time.

6. Why Stephen Might Like It

• If he appreciates food + drink: Lisbon is paradise. Fresh grilled sardines, vinho verde, pastel de nata, endless good wine.
• Socially warm: People are friendly, less brusque than Parisians or Berliners. Easy to strike up conversations.
• Great travel hub: quick flights all over Europe, especially cheap on budget carriers.
• Outdoorsy balance: the city itself is hilly and walkable, but beaches and hiking are right at your doorstep.

7. Possible Downsides

• Bureaucracy: paperwork can be slow, old-school, frustrating.
• Infrastructure: charming but occasionally creaky (steep hills, cobblestones, slower transit).
• Rising costs: expat boom has pushed up rents, and locals sometimes resent gentrification.
• Summer tourism crush: some neighborhoods feel overrun.

✨ Summary: Lisbon offers the best of both worlds — cultural richness and European charm with sun, affordability, and friendliness that make it easier for North Americans to integrate. It’s not just a city to visit; it’s one of the most liveable global cities if you want a mix of romance, community, and sunshine.

Do you want me to make a side-by-side comparison of Lisbon vs Barcelona (since they’re often the two “dream Mediterranean cities” North Americans consider)?

Ah, yes — Cascais! If Lisbon is the buzzing, colorful, creative capital, Cascais is like its elegant, seaside counterpart. It’s only about 30 minutes by train from Lisbon, so many people live in one and play in the other. Here’s how it stacks up as a place to live:

🏖️ Cascais as a Place to Live

1. Atmosphere

• Formerly a fishing village, now a chic coastal town with palm-lined promenades, beaches, yachts, and cobblestone streets.
• Feels more laid-back, affluent, and resort-like than Lisbon.
• Think: ocean breezes, pastel villas, a slower, calmer rhythm of life.

2. Natural Beauty & Outdoors

• You’re literally living on the Atlantic coast. Walks along the seaside esplanade, surfing, paddleboarding, and beach lounging are part of everyday life.
• Close to Sintra-Cascais Natural Park — forests, cliffs, castles, and hiking.
• Climate: same as Lisbon, but you get that constant fresh sea air.

3. Cost of Living

• More expensive than Lisbon, especially in housing.
• Upscale feel: think boutique shops, luxury condos, high-end restaurants.
• That said, still cheaper than places like California or New York seaside towns.

4. Community & Language

• Very expat-heavy, especially families, retirees, and international professionals.
• English is widely spoken. You’d almost never struggle day-to-day.
• Social life may feel more “expat bubble” than deeply Portuguese, depending on how you approach it.

5. Why You (Jay) Might Like It

• If Lisbon is a bit too hectic, Cascais gives you a serene base while keeping Lisbon accessible for culture/work.
• Perfect for writing: calm, inspiring coastal views.
• Photography heaven: ocean cliffs (Boca do Inferno), sunsets, harbors.
• Still close enough to Lisbon’s intellectual, literary, and AI/tech communities when you want stimulation.

6. Why Stephen Might Like It

• If he loves the outdoors and the ocean, Cascais is unbeatable. Surfing, swimming, sailing, biking trails — all on his doorstep.
• Relaxed lifestyle: more cafés by the water, less hustle.
• Easy to host visiting friends/family: who wouldn’t want to visit a picturesque coastal town 30 minutes from Lisbon?

7. Possible Downsides

• Less cultural density than Lisbon: fewer concerts, events, and intellectual ferment.
• Can feel sleepy in the off-season (especially compared to Lisbon’s year-round buzz).
• Higher housing costs, especially for beautiful properties with ocean views.
• Some neighborhoods are very expat-dominated — less “authentically Portuguese.”

✨ Summary: Cascais is ideal if you want coastal tranquility and beauty, but with Lisbon close enough to dip into when you crave urban culture. It’s often seen as the best of both worlds — especially for North Americans who like the idea of a softer landing in Europe, with English-friendly infrastructure and a beach-town vibe.

Would you like me to do a Lisbon vs Cascais head-to-head comparison — so you and Stephen can see which fits better as a base?

Great one — Lisbon, Cascais, and Geneva all scratch different itches. Let’s do a head-to-head comparison so you can see what kind of life each city offers.

🥂 Lisbon vs Cascais vs Geneva

🌆 Everyday Atmosphere

• Lisbon → Vibrant, creative capital. Bustling but not overwhelming. Music, trams, nightlife, a sense of history and soul.
• Cascais → Seaside calm, upscale, expat-friendly. Less intensity, more walks by the water and sunsets.
• Geneva → Polished, international, buttoned-up. Feels more like a global hub for diplomats and bankers than a playful city.

🌞 Climate

• Lisbon → Mediterranean-Atlantic: ~300 sunny days, mild winters, hot but breezy summers.
• Cascais → Same as Lisbon, but cooler breezes off the ocean, less urban heat.
• Geneva → Four seasons. Glorious summers by the lake, snowy winters. Less sunlight overall, and darker winters compared to Portugal.

💸 Cost of Living

• Lisbon → Affordable compared to North America and Northern Europe, though rising quickly.
• Cascais → More expensive than Lisbon (especially housing), but still cheaper than Geneva.
• Geneva → One of the most expensive cities on earth — housing, dining, groceries, everything.

💬 Language & Social Ease

• Lisbon → Portuguese is official, but younger generations + expat circles speak English fluently. Easy to integrate.
• Cascais → Extremely English-friendly; heavy expat presence. Integration even easier than Lisbon.
• Geneva → French dominant, but English is common in international institutions. Social circles can feel formal and harder to break into compared to Portugal’s warmth.

🌍 International Connectivity

• Lisbon → Great airport hub, especially to Europe, Africa, South America. Direct flights to NYC/Boston.
• Cascais → 30 minutes from Lisbon airport; same benefit.
• Geneva → Major hub for diplomacy, finance, NGOs. Airport connects strongly to Europe, less to the Americas.

🧑‍🤝‍🧑 Vibe & Social Life

• Lisbon → Café culture, music (fado, jazz, DJ scenes), creative energy, younger crowd. Friendly, warm, expressive.
• Cascais → More family-oriented and serene. Social life revolves around expat gatherings, cafés, and outdoor activities.
• Geneva → More reserved, international but formal. Social life often revolves around professional circles, not spontaneous neighborhood energy.

🌄 Nature Access

• Lisbon → Beaches and hiking day-trips, but you live in a city.
• Cascais → Daily seaside walks, surf breaks, biking trails, Sintra mountains right behind you.
• Geneva → Lake Geneva, Alps at your doorstep. Skiing, hiking, sailing. Arguably the most dramatic outdoor access of the three.

⚖️ Why You (Jay) Might Like...

• Lisbon → A writer’s city: romantic, photogenic, soulful, intellectually alive.
• Cascais → A calm, seaside base with inspiration for writing + photography, close enough to Lisbon’s cultural scene.
• Geneva → Pristine, elegant, order-loving. Might feel a bit too orderly compared to your taste for energy and conversation. But if you lean into outdoorsy weekends and international connections, it’s rewarding.

⚖️ Why Stephen Might Like...

• Lisbon → Food, nightlife, warm social energy. A fun base with good travel options.
• Cascais → If he loves the ocean and outdoors, Cascais could be heaven — less nightlife, more surf + relaxed vibe.
• Geneva → If he values order, safety, multilingualism, and outdoor adventures (skiing, lake swims), Geneva’s a great fit. But social life might feel reserved compared to Portugal.

✨ Bottom Line

• Lisbon = best for cultural energy + affordability.
• Cascais = best for daily seaside life + tranquility (with Lisbon close by).
• Geneva = best for outdoor adventure + polished, international prestige, but less warmth and much higher costs.

Do you want me to sketch out a “Which city fits which type of lifestyle/personality” matrix for you and Stephen — almost like a decision tool?