I love Tokyo. I think it’s one of the most fascinating cities in the world. I love the organized crowds where you would expect chaos. I love how it is a fast-paced, contemporary city that still honors its traditions. It’s also a massive city with an endless array of incredible things to see and do. No matter how many times I visit (and no matter...

After I graduated from college, my friends and I got really into poker. Every Sunday night, we would meet at our buddy Joe’s apartment and play for a couple hundred bucks total. It was our weekly ritual. With the HBO show Entourage in the background, we’d order food and, huddled around a small table, catch up before getting ready to go to our boring...

Medellín is the second-largest city in Colombia and a favorite among the digital nomad crowd. Nestled in the Aburrá Valley, the city has great weather year-round, earning it the nickname: “the City of Eternal Spring.” I spent a lot of time in Medellín. While the city has a troubled past, today, it’s a vibrant and innovative metropolis. I’d go back...

A few years ago, one night over dinner with some friends with whom I shared a love of gourmet food, sushi, great cocktails, politics, and movies, we realized that in all the years we’d known each other, we had never taken a trip together. As we all had lots of points and miles saved, we thought about how fun it would be to go somewhere spontaneously....

Berlin is a cool city. Multicultural and artsy, Germany’s capital city is home to artists and creatives from all over the world. A hub for freelancers, digital nomads, and entrepreneurs, the city also boasts excellent museums, a boisterous nightlife, and every type of cuisine imaginable. You could spend weeks (months!) in this city and not get bored....

Hello there! It’s been a while since I’ve written a real blog. Sure, there have been lots of how-to posts, itineraries, where-to-stay suggestions, and old-post updates to keep helping you travel on a budget. But it’s been over a year since I wrote anything personal — and it’s been even longer since I shared a story from the road. In the beginning...