Travel Diary: Stephanie Chai’s Tokyo Hit-List For A Weekend Of Food, Shopping & Fun With Girlfriends

When a wave of wanderlust hits, you can always count on Stephanie Chai’s Instagram account as the gateway to your next travel destination. The founder and CEO of TheLuxeNomad.com is always jetting off on an enviable new adventure around the world: This year alone, Steph has been on the road every 2 weeks, including Sydney, Niseko, Italy and Dubai. Ironic as it sounds, the intrepid beauty actually wishes to go easy on the travels – but one mustn't complain when running a luxury travel firm comes with its own perks. Occasionally though, Steph swaps her business cap with a tourist hat, like that time she and her best friends Jasmine Kamal and Deborah Henry went on a girls trip to Tokyo. Here, we catch up with Steph for recommendations in the glitzy city of food, culture, and sights, and pro-tips on assimilating to the Japanese culture.

1. Of all the destinations you’ve been to, why is Tokyo special?

Above Stephanie and her best friends, Deborah Henry and Jasmine Kamal. (Photo: Courtesy of Stephanie Chai)

Tokyo is an amazing city with various pockets to discover – the old and the new, the traditional and the slightly out-of-whack. I love how much thought the Japanese put into anything they’re doing. Food is always tasty, presented perfectly, and a work of art on its own. Buying something from a store? Even if it is small, they will take the time to wrap it in as an art form.

2. What was the highlight of this trip?

Above A funky spot at Omotesando. (Photo: Courtesy of Stephanie Chai)

This was planned as a fun girls trip with my best friends Jasmine Kamal and Deborah Henry. I was there from Monday to Friday for work, then I stayed on for a few days and my girlfriends flew over. The intention was to eat well, have fun, and shop a bit, which we did! In my free time, I headed to Omotesando. It is one of the shopping streets in Tokyo, akin to Fifth Avenue in New York if you will. It is lined with lush green trees with all the big luxury brand names and their uniquely designed stores framing the street.

3. What were you most excited about this weekend?

Above Two Rooms Grill at dinnertime. (Photo: Courtesy of Stephanie Chai)

I was just happy to spend time with the girls, hang out with friends who live in Japan, and eat delicious Japanese food. We went out for drinks in Two Rooms Grill, a trendy bar in Omotesando, and went to an underground rustic Japanese restaurant and had a good laugh there.

4. And the most fun thing you did?

Above View from the Ascott. (Photo: Courtesy of Stephanie Chai)

We had a 2-bedroom apartment at Ascott overlooking the Imperial Palace, which was amazing as it had just opened then. It’s a really nice place to stay in and I highly recommend it. Unfortunately, Jasmine loves to sleep in and by the time we went out, all the lunch places were closed but going to Ginza Six with the girls was fun. It is one of my favourite shopping centers as it might be the most beautiful mall I’ve ever been to. When it first opened, they had collaborated with Japanese artist Yayoi Kusama, so the interiors were adorned with her iconic bubble designs. The floor with restaurants is great, too – do stop by for high tea if you can!

5. How was the food like? what were the standout dishes?

Above Beef Yakiniku. (Photo: Courtesy of Stephanie Chai)

Favourite beef BBQ is by far Yakiniku Ushigoro in Roppongi (this outlet is the best but if it is full, head to the Ginza one). Must-try’s are: The oxtail soup, salad, the beef udon, and their special beef which just melts in your mouth… every time I go to Tokyo, I head here!

6. What struck you the most about Japanese etiquette?

Above Stephanie and her girls. (Photo: Courtesy of Stephanie Chai)

Tokyo is more a wildcard city but in Kyoto where I went for work, there is a proper way to go about things. For example, setting an appointment would require rigorous steps to ensure who we were speaking to, whom we had to talk to, and ensure the most out of our time there: They are very organised and orderly. The Japanese are also honourable, honest, and meticulous. Everything is done with precision. Another striking thing is that many elderly people are still working, which tells us a lot about the Japanese quality of life.

7. Any memorable takeaways from the culture?

Above Stephanie, Jasmine and Deborah enjoying Tokyo after sundown. (Photo: Courtesy of Stephanie Chai)

I’m generally animated and loud but in Japan, I dropped an octave lower. In the train, you don’t pick up your phone and chat as that’s frowned upon. You naturally assimilate and become more mindful of the way you speak, gently and definitely more polite than usual.

8. Surprising discoveries in Japan?

Above Ushiguro beef. (Photo: Courtesy of Stephanie Chai)

For an international city, Tokyo is still very true to its roots. And, there are so many amazing restaurants! Thanks to my friends who reside there, they knew which ones were good, made the necessary arrangements, and brought us to good neighborhood spots. On my own, I think I’d have trouble making a booking or even knowing places. The menus are in Japanese so in that sense, it’s not the most tourist-friendly.

9. What do you love most of this country?

Above Surprises are at every corner: Like this pram of 8 Persian cats. (Photo: Courtesy of Stephanie Chai)

I love the people and Japan itself. I love how structured and traditional it is; yet it’s modern and accessible. I remember when I was at the train station in Kyoto, there was a man who just stood there all day and greeted everyone with an 'arigato gozaimasu' and on this flip coin, I was walking down Omotesando and came across a man with a pram and eight Persian cats inside! He was just sitting and chilling on a bench whilst everyone walked by and fawned over his cats. That’s Tokyo – always a little quirky!

10. What would you recommend first-time visitors to do?

Above The streets of Tokyo. Photo: (Courtesy of Stephanie Chai)

Go sightseeing. Take a trip to see the Tokyo Tower - it stands taller than the Eiffel Tower, which inspired its creation. Besides being a favourite for the stunning views it provides, it’s also a communication antenna used for television broadcasting. Worthy of visiting is the Zozoji Temple, and Kyu-Shiba-rikyu as they are nearby. Go shopping and eat your heart out. Indulge in the freshest seafood, authentic sushi, and melt-in-your-mouth Matsusaka, Kobe, or Omi beef!

Topics

Stephanie Chai girly holiday weekend getaway luxe nomad Tokyo

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