Taiwan: Rewriting The Rules

Meet Jake Hemingway, an 8-year-expat in Taiwan who traveled from Taipei to Kenting by skateboard to promote Taiwanese culture and to advocate adventure, taking risks and living outside your comfort zone.

Jake Hemingway first arrived in Taiwan for a two year stint as a missionary. Eight years later, the American expat has made a life for himself in Taiwan and continues to be one of the country’s biggest promoters. He chose to rewrite the rules and take to the roads of Taiwan on a skateboard, covering 452km in five days to discover the length of Taiwan, from Taipei in the north to Kenting at the southernmost tip. Having grown a huge following of fans that follow along on his adventures, Hemingway regularly plans travel adventures by skateboard, bike or foot and hopes to encourage locals to see more of their beautiful home. He’s an advocate for personal freedom, stepping outside your comfort zone and not being held back by societal conventions.

Tripsle: What’s kept you in Taiwan for so many years?

Jake: There’s something unique here, in a way that’s entirely different from the US. To me, it’s a stunning little island. It’s so convenient to live here and travel around, you can go anywhere you like. You can also discover a very distinct culture here too. But the most captivating thing would have to be the hospitality of the natives. They are so enthusiastic, warm-hearted, and easygoing which continues to impress me.

Tripsle: Taiwan is renowned for it’s food, what are your favorites?

Jake: I am really fond of the snacks and street food in the night markets. Personally I prefer simple and local food. There are lots of famous night markets all over, like Shilin Night Market and Shida Night Market in Taipei, which are distinct from those in other towns and regions. It’s a popular spot for hanging out, shopping and whiling away a few hours at the local arcades too.

Tripsle: Any top Taiwan recommendations?

Jake: I would highly recommend braving a taste of stinky tofu when visiting the night markets. No matter whether you love it or not, it is a very traditional food here. You cannot find it in other places so whenever my friends and relatives come to visit, I’ll get them to try it out.

Tripsle: You have chosen to travel around Taiwan in a unique way, why travel by skateboard, bike and foot?

Jake: I’ve lived in Taiwan for eight years and there are still places I haven’t seen. Venturing by skateboard, bicycle or simply on foot allows me to travel in a different way. Modes of transport like a skateboard, which is relatively slow in speed, enable me to get a slow-motion look at everything I pass. By traveling in different ways, I can discover Taiwan from different angles.

Tripsle: What special and meaningful memories do you have from your trips?

Jake: On the journeys, we always encounter different people, some of them have become our friends and some of them have offered help to us. They are all so warm-hearted. I met a group of local, and we were initially stranger, but after a few chats, they have now become my traveling companions. They even went to the US to visit me. The journey has really given me great opportunity to meet new friends.

Tripsle: Do you have a favorite route?

Jake: I would say the route along the east, especially around eastern Taiwan and Hualien. You can choose to journey along the coast or through the hills. It depends on which kind of experience you are looking for. I love the natural landscape on the east coast: it’s not densely populated, there are less vehicles, and you are free to explore the natural beauty of the scenery.

Tripsle: Do you plan to explore Taiwan in other ways after your most recent trip?

Jake: We had a pretty tight schedule for the previous trip due to time restraints. So in the future, I plan to prolong the journey so that we’re not always in a rush. By taking more time, we can discover and understand more about this beautiful place – both for myself and for those who follow along on the journey.