While Japan is emerging as the latest travel destination, it feels more like coming home for Jake Tokayer. Teahouse Trails, Jake’s touring company, has become an industry leader in kosher tours for young adults, families and small groups. He has made it his mission to create immersive journeys that blend Japanese culture with a deep exploration of Jewish history in the Far East. These tours are meticulously curated for each group, offering a unique opportunity to connect with Japan’s rich traditions while uncovering its lesser-known Jewish legacy.
Jake started his business leading kosher backpacking tours, a style of travel best appreciated by young professionals eager to see Japan on a budget. Now, he focuses most of his energy organizing private tours for families and small groups, while still leading a few backpacking tours each year. Jake has also created kosher packages in luxury hotels. Now Chabad-affiliated chefs can prepare and serve kosher gourmet meals to groups both small and large.
Teahouse Trail’s owner ensures that each journey delves into the stories of ancient and contemporary Jewish history in the Far East. Participants can hear about the Jewish pioneers along the Silk Road, the rediscovery of a Jewish cemetery in Yokohama, and of the righteous among nations Chiune Sugihara. Visiting Kobe for Shabbat, visitors will meet its Jewish community and learn about the city’s pivotal role in providing refuge to Jewish families fleeing persecution during the Holocaust. Japan has a unique and often overlooked Jewish history, and Jake expertly weaves these narratives into the cultural and historical highlights of each trip.
Jake’s passion for connecting Jewish travelers with the Far East stems from a legacy deeply rooted in his family. Jake emphasized that he is “standing on the shoulders of giants,” because it all started with his grandfather, who first landed in Japan as an United States Air Force chaplain, and became a pillar of the Jewish community in Tokyo. As a chaplain, Rabbi Tokayer was stationed in the Far East for several years. He was fascinated by the unknown Jewish history in Japan and began to document it. At the time, there was even a small Jewish community of businesspeople and World War II refugees.
After returning to the United States, Rabbi Tokayer found that Japan never left his thoughts. He maintained close ties with members of the Japanese community and, not long after settling in New York, published an article in The New York Times about a Jewish cemetery he had rediscovered in Nagasaki. The piece drew the attention of the Lubavitcher Rebbe, whom Rabbi Tokayer had coincidentally already planned to visit in Crown Heights. During their meeting, the Rebbe offered a guiding principle: Focus on the living rather than the deceased. With this advice, the Rebbe encouraged Rabbi Tokayer to return to the Far East to serve as a spiritual leader for the Jews in Japan and scattered communities across the region.
What began as a two-year assignment in Japan evolved into a decade-long journey for the Tokayer family. Settling in Shibuya, Tokyo, Rabbi Tokayer became a prominent representative of Jewish life in the Far East. Jake’s father and aunt were born and spent much of their childhood immersed in the unique cultural and historical fabric of the region.
As a historian and scholar of Jewish history in the Far East, Rabbi Tokayer cultivated deep relationships and built a legacy of scholarship. His works, published in both English and Japanese, sought to illuminate what he described as “the page written out of history.” This mission defined his life, as he dedicated himself to educating others about the Jewish experience in the region.
For four decades, Rabbi Tokayer led kosher tours across Asia, sharing the stories of Japan’s post-World War II Jewish community and China’s ancient Jewish heritage. Jake’s first impression of Japan was at age 13, on one of Rabbi Tokayer’s tours as a bar mitzvah gift. He got to see where his father grew up and the fascinating Jewish history there. The experience left an indelible impression on Jake, shaping his appreciation for both his family’s and the Jewish people’s history in the Far East.
Like his grandfather, Japan never escaped Jake’s mind. During his gap year, Jake went back to Japan to backpack on his own. “My goal was to experience the history and wonders again.” And that he did. A year later, while he was a student at Yeshiva University, Jake tried his hand at leading a tour, just like his grandfather. He took three other students with him for a two-week kosher backpacking tour of Japan. That was the start of something great. After his military service in the IDF, Jake has led seven backpacking tours to Japan and taken over 80 people along with him. Teahouse Trails is a one-of-a-kind experience touring Japan through a Jewish lens.
Through his experience, Jake has become an expert in kosher logistics of premium adventures in Japan. “I am incredibly passionate about continuing the legacy of teaching Jewish history in the Far East,” he said.
Teahouse Trails has a kosher backpacking tour scheduled for March, in time to witness the country’s legendary cherry blossom season. There are few spots remaining. “March is a spectacular time to go. Everything is right there at your fingertips and there is so much to uncover and experience,” Jake said.
Japan is listed as one of the top three safest countries in the world for Jews. “You experience a totally different culture that you didn’t even know existed,” Jake. “The people are friendly and courteous, and the streets are famously pristine.”
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