The Best Decision I Made in Tokyo Was Hiring a Guide — Here's Why You Should Too

Shibuya, Tokyo
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I’m a seasoned traveler with an intuitive sense of direction and a knack for Google Maps. I have successfully navigated cities across the globe, from Kigali to Chengdu and La Paz. But on my first trip to Tokyo, I got really turned around to the point where it eroded my navigational confidence. So when I returned a few years later, I decided to consult a professional.

Omoide Yokocho, Tokyo
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Japan is known for its rental friends, people you can hire for an hour or two to keep you company as you dine out or go shopping. But I didn’t need a buddy, I needed an expert who could navigate the streets with ease.

I started by using a guide at my hotel, the OMO5, in Otsuka, a suburb north of the city. Every guest of the property has access to OMO rangers, in-the-know guides who help foreigners discover the surrounding neighborhoods and uncover locals-only spots.

In the lobby, I met my ranger, who was conspicuously dressed in a bright yellow shirt and wide-brimmed safari hat. He instructed me to choose a handful of experiences off an activities board. After I made my selection, we headed off for the first spot, a ‘hidden’ tempura restaurant in Otsuka.

OMO5 Tokyo
Courtesy of Hoshino Resorts

Once we were seated, my guide ordered me a selection of tempura (deep fried zucchini, prawns, and lotus root) and a glass of sake. He explained that the owners of the restaurant, an elderly couple, had lived in the neighborhood their entire lives and cooked together for more than 30 years. I felt like a true insider, as though I had been invited into someone’s home.

On the way back to the hotel, I followed the ranger as he confidently led me along the labyrinth-like streets, pointing out cool shops and other restaurants. It felt good to relinquish all control.

When I checked into another hotel, the Hotel Tsuki, which was located on the other side of the city, I wasn’t able to take my Omo ranger with me. So I requested the help of InsideJapan Tours, an outfit that set me up with an American guide named Tyler Palma. Tyler had been living in Tokyo for years and spoke perfect Japanese. I asked him if we could hit up a cool wine bar and try some local wines and he recommended Kiraboshi, an under-the-radar drinking hole near the Roppongi district.

Shinjuku, Tokyo
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In the dimly lit room, our sommelier, Keitaro Oyama, an industry vet for 22 years, poured wines from all over the country, paired with dishes that spotlighted local flavors. Some of the combinations I couldn’t have possibly dreamt up — like a bowl of dashi broth accompanied by a glass of sparkling wine.

At the end of the wine-and-food-fueled night, Palma hailed me a cab and gave the driver instructions to get to my hotel. I sat in the back seat, taking in the bright lights as we whizzed across the city. I didn’t even miss my beloved Google Maps.

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