See photos of a meal at Vintage Cave

The Hawaiian Islands are celebrated for distinct local cuisine—fresh pineapples, bowls of poke, the infamous loco moco, and a healthy love of Spam—but Honolulu certainly doesn’t scream haute cuisine.

Tides are shifting though. A generation of chefs inspired by James Beard winners Alan Wong and Roy Yamaguchi is changing the face (albeit slowly) of Oahu’s culinary landscape. On the North Shore, Opal Thai’s simple set-up and charismatic owner have made Haleiwa more than just a legendary surf destination. In Kailua, Alejandro Briceno and Lindsey Ozawa translated the success of their post-club favorite, V-Lounge, into a more traditional American-Italian joint that marries sleek furnishings with a locally sourced menu from chef Kevin Lee (a former sous chef at NYC’s Dovetail). Then there’s Town, a Honolulu hotspot where we recently found Alan Wong eating at the bar, straight off a flight from San Francisco.

Further off the radar is the ambitious and, frankly, mysterious Vintage Cave. Why off-the-radar? For one, this $295-a-head high-roller spot is situated through a discrete door in the middle of a parking lot under the Ala Moana Center mall. Investor Takeshi Sekiguchi dropped $20 million on the restaurant, filling the space with Picasso drawings and Baccarat crystal (it’s estimated that there’s $1 billion worth of art down there). Then he did the unthinkable—handed a relatively untested chef a blank check to create the restaurant of his dreams, with one caveat: Don’t compromise.

That chef is 29-year-old Chris Kajioka, a Culinary Institute of America grad and Hawaiian native whose resume includes short stints at Per Se and the Willows Inn. Getting to grips with the exclusivity of Vintage Cave isn’t easy—after this year, the restaurant will become fully members-only, with entrance fees starting at $5,000 and climbing toward $500,000—and Kajioka’s not immune to the insanity of it all. But he’s also not taking anything lightly, focusing all of his energy on crafting an extravagant, 20-plus course tasting menu that seeks to give patrons their money’s worth—even if that means shaving a few extra black truffles here and there for good measure.

When we caught up with him on a recent trip to Honolulu, Kajioki spoke candidly about his goals, his pedigree, and the various challenges of appealing to the 1 Percent while trying to thrill the most curious of eaters. Here, in his own words, is the story of Vintage Cave so far.

Interview by @onceuponabite