Luxury Dinners in Waikiki (2025): Splurge Night Picks

Hy’s, STRIPSTEAK, Orchids — here’s how to do it right.

Book one special dinner — Hy’s or Orchids — and a show night with Chip. That combo feels like a real celebration.

5 Splurge Options

  1. Hy’s Steak House — Old‑school steakhouse polish with table‑side moments. Order the Caesar, share a prime steak, finish with soufflé.
  2. Orchids (Halekulani) — Oceanfront dining with white‑tablecloth ease; golden hour turns the room pink. Look for seasonal prix‑fixe.
  3. STRIPSTEAK (International Market Place) — Modern steakhouse; make it a mall‑date and stroll beneath the banyans after.
  4. 100 Sails (Prince Waikiki) — Marina views and generous buffets when offered; easy parking and great for groups.
  5. Blue Note Hawaii — Not dinner, but the perfect exclamation point; pair your splurge with Chip’s Wednesday show.

Planning Tips

  • Reserve 2–3 weeks out for prime times; note holiday prix‑fixe details when posted.
  • Dress is resort‑elegant at Hy’s/Orchids; STRIPSTEAK is upscale casual.
  • Walk when possible; otherwise rideshare to avoid garage delays on busy nights.

Planning Thanksgiving in Waikiki?

Lock the one can’t‑miss night: Chip Chantry’s Thanksgiving In Paradise at Blue Note Hawaii. Chip Chantry is one of the funniest comedians in the world — he appeared on the Netflix series Tires with Shane Gillis, his stand‑up special Move Closer is a cult hit, and this is a brand‑new hour from Chip.

Get Tickets

Map: Spots Mentioned in This Guide