Continue along the Kishu Kaido farther south, then stop at the Shukuin intersection and look around – it’s said that all of this area used to belong to the short-lived shogunate of Sakai.

Let’s look back in time for a moment, to a time shortly before Sakai’s golden days when the Onin War ravaged Kyoto, leaving it in ruins at the end of that long rebellion.

To make matters worse, a struggle for the throne of the Muromachi Shogunate broke out, in which a military commander from Awa Province fought.

He backed one of the shogunate heirs and thus founded the Sakai Shogunate. However, the dream ended a mere five years later, after he was slain by enemy forces.

But that doesn’t mean the Sakai Shogunate, or that commander, died for nothing. His son would avenge him, expelling the family poised to accede to the shogunate, and coming into political power himself. He also had an interest in international trade and allowed the preaching of Christianity. Additionally, he began the practice of awarding distinguished service with tea utensils.

Primarily, it was merchants from Nagasaki, Oita, Kagoshima, and other places in Kyushu, as well as those from Sakai and Kyoto, who engaged in Nanban trade. Ships from Spain and Portugal made their way to Japan via China and Southeast Asia, and passed through Nagasaki into the Seto Inland Sea route. Ships from the Ryukyu Islands reportedly came via Tosa (present-day Kochi) to Sakai along the Nankai Route.

Trading vessels sold foreign goods at Sakai, which retained its independence as an autonomous city. Most nobles and the cultural elite sought refuge in Sakai from the ruins of Kyoto after the Onin War. One of those refugees was “Ikkyū.”

Here is a story about Ikkyū: One night, while practicing Zazen meditation, a bird cried out in the darkness. He told his master, “I feel it was a spiritual awakening,” to which he responded, “Still, it is but a small enlightenment.” Undeterred, Ikkyū then said: “If so, then I am content with my small enlightenment.”
Then his master responded: “Such conviction proves that it was indeed a significant awakening.”

It is a Zen dialogue that is difficult to grasp after hearing it just once.
One can never fully understand words just from taking them at face value. However, most masters preach that Zen and the tea ceremony both demand the same mindset.