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Jake Sullivan

How to Live Like Royalty in Southeast Asia for Under $1,800 a Month

April 8, 2026April 8, 2026 by Jake Sullivan
How to Live Like Royalty in Southeast Asia for Under $1,800 a Month

Imagine waking up to a warm breeze, stepping out for a fresh mango smoothie that costs less than a dollar, and spending your afternoon at a rooftop pool that belongs to your own apartment building. This is not a fantasy built for the ultra-wealthy. It is a completely real, fully attainable lifestyle that thousands of … Read more

Categories Travel Tips

The Remote Work Lie: 8 Jobs That Sound Like a Dream but Are a Travel Nightmare

April 6, 2026April 6, 2026 by Jake Sullivan
The Remote Work Lie: 8 Jobs That Sound Like a Dream but Are a Travel Nightmare

Picture this: you’re sipping a coffee at a café in Lisbon, laptop open, ocean breeze drifting in, and your inbox stays perfectly quiet. It sounds like the best ad for the modern working life. And honestly, millions of people bought into exactly that story. In 2024, an estimated 35 million people worldwide identified as digital … Read more

Categories Travel General

Redlining the Air: Why These 8 Airlines Are Permanently Off Our Radar

April 6, 2026April 5, 2026 by Jake Sullivan
Redlining the Air: Why These 8 Airlines Are Permanently Off Our Radar

There’s a reason you instinctively feel uneasy when you board a flight with an airline you’ve never heard of. That gut feeling? It might actually be saving your life. Aviation is arguably the safest way to travel, but that safety is not guaranteed equally across every carrier on the planet. Some airlines operate in a … Read more

Categories Travel General

The Scam Census: 10 Cities Where You’re Guaranteed to Get Pickpocketed

April 5, 2026April 5, 2026 by Jake Sullivan
The Scam Census: 10 Cities Where You're Guaranteed to Get Pickpocketed

You plan the trip of a lifetime. You research the hotels, the restaurants, the hidden gems. You pack light, book smart, and land with wide eyes and a full wallet. Then, somewhere between the selfie at the landmark and the dash back to the metro, it happens. Your pocket is empty. Your phone is gone. … Read more

Categories Travel General

The Loneliness of the Long-Termer: 10 Things Nobody Tells You About Life on the Road

April 5, 2026April 5, 2026 by Jake Sullivan
The Loneliness of the Long-Termer: 10 Things Nobody Tells You About Life on the Road

There’s a version of long-term travel that looks like a sun-drenched Instagram feed: laptop on a rooftop café, a cold drink in hand, a view that makes your friends back home press the “like” button with barely concealed envy. It looks easy. It looks luminous. It looks like freedom. The reality, for most people who’ve … Read more

Categories Travel General
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