How to Book
Fill out our CUSTOM TOKYO FORM or email us at custom@contexttravel.com to get started.
Itinerary Inspiration
- We could explore Old Tokyo and Uneo Park while discussing the role of a green public space in a dense city like Tokyo, and how Tokyoites lived in past decades.
- We could create a layover tour, getting you outside the airport and immersed in the impressive architecture and consumption culture of Tokyo, followed by an authentic meal with your guide.
FAQ
- How many days would you like the tour to be?
- Do you have specific goals for your trip?
- Which sites and venues would you like to prioritize? Do you want to just pass by or explore inside as well?
- Do you have any mobility concerns?
- Who are you traveling with? What are their ages and interests?

Jay received a Master's degree in Urban Planning from the University of Tokyo where he focused his research on the conservation of historic spaces and landscapes with a particular focus on food production and the agricultural families and communities in and around the city. Having been a resident of both rural and urban Japan, Jay has a particular appreciation for the visible transformation of the country's settled environments as ideas, resources, and the culture itself has changed over the past couple of centuries. While he has lived in a variety of cities and towns in the US, Syria, Russia, the UK, and Japan for study or work, he finally settled on Tokyo as home. He enjoys sharing information about its hidden history, constant development and endless layers.

Troy, born of a Japanese-American family, has lived nearly half of his life outside of the States. Given this, his study of cultural anthropology focusing on contemporary Japanese culture, and 14 years involved in education while living in Japan may be a natural result of this upbringing. He feels fortunate that life in Japan has allowed him to continue his passion for travel and people and afforded him ample opportunity to help others discover new vistas, ways of thinking and experiences in places ranging from Japan to Thailand to Papua New Guinea. Troy firmly believes that everyday scenes and events can provide some of the greatest insights into a new place and the key to an appreciation of the richness of a culture can often be found by simply learning to recognize the "mundane" patterns as they are reproduced in different contexts and varied over time.

Kara has suffered from wanderlust for most of her life. Leaving her native New York to bicycle across America as a teen, she then backpacked through Europe for a year before landing in Japan, where she has made her home since 1985. After graduating magna cum laude with a degree in Art History at Tokyo’s Sophia University, along with certification in Fine Art Appraisals at New York University, she founded her own art gallery supporting emerging young Japanese artists. She has curated numerous exhibitions, organized symposiums, and lectured frequently at colleges including the prestigious Keio University. Kara is a regular contributor to magazines and newspapers on Japan’s art scene, and is the author of “Contemporary Art Walks” in a Tokyo guidebook published by Stone Bridge Press. Media appearances include interviews in 'Newsweek', 'New York Magazine' and prime-time TV shows. She speaks and reads Japanese fluently, and spends her free time pursuing first-hand experience of Japan’s culture and subculture. With a particular interest in indigenous Buddhist practices, she has endured rigorous Yamabushi training with ascetic mountain-dwelling monks, and traveled 30 countries including remote areas such as Lombok and Mt. Kailash in Tibet. More of an urban explorer these days, Kara’s current passion is unraveling hidden aspects to Tokyo, always with a unique insight into visual anthropology.
Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.