Experience Hawaii your way with the freedom to choose – or divide your stay between – any of four enchanting islands: O‘ahu, Maui, Kaua‘i, or the Big Island of Hawai‘i. Each six-night getaway for two includes luxurious accommodations at an Outrigger Resort, and an adventure to explore the island. Dive into history at Pearl Harbor, watch the sunrise over Haleakalā, explore volcanic landscapes in Kona, or cruise through the cinematic beauty of Kaua‘i.

Whether you savor six serene nights in one paradise or split your stay between multiple islands for the adventure, every moment is curated for wonder, relaxation, and discovery. With Winspire’s expert booking and concierge service, your dream island-hopping Hawaiian escape begins exactly how you imagine it.

• 6 nights at a menu of Outrigger Resorts – choose the islands and duration that inspire you most.
  • Outrigger Waikiki Beach Resort – City View room
  • Outrigger Kona Resort and Spa – Resort view
  • Outrigger Kauai Beach Resort & Spa – Garden View room
  • Outrigger Ka’anapali Beach Resort – Premium Garden View room
• Your choice of two experiences from a curated selection of adventures

In addition to the island stay, winner will recieve a $1,000 credit to apply to the airfare purchase(s) to the island of their choice.

Total value of trip, including Winspire Hawaii package and airfare credit is $4,999.00

**You must be at least 18 years old to enter and live in the continental US.