Oprah Winfrey hops to Kona the week of a wine-and-wellness summit

Oprah Winfrey flew from Kahului to Kona on the morning of May 23, 2026, a 26-minute hop in her Gulfstream G700 (N540W) at 15,000 feet. The brief inter-island leg — just 357 knots at peak — is a routine connector between the Maui and Hawaii Island properties she has owned for years.

Kona is host this week to the Hawaii Food & Wine Festival's Island of Hawaii showcase, a multi-day event running May 21–24 that draws chefs, vintners, and philanthropists — a circuit Winfrey has supported in the past, per festival materials. No public appearance by Winfrey has been confirmed, but the festival's signature farm-to-table dinners and ocean conservation panels align with her well-documented interest in food systems and Hawai'i stewardship.

The flight follows a week of unusual routing: Telluride to Santa Barbara, then to Kahului on May 22, and now onward to Kona. Winfrey's primary Hawaiian base is on Maui, where she owns more than 1,000 acres; the Kona side offers access to her property near Kealakekua and the island's west-coast resort corridor. For a media mogul who has called her private jet "the best gift to myself" — per a FIV Magazine profile — this is simply the most efficient way to cover 120 miles of Pacific coastline between meetings.