Voting in the HAWAIʻI Magazine 2027 Readers' Choice Awards opens November 6, and yes, there is a trip attached. One lucky voter will take home two round-trip tickets on Hawaiian Airlines and a four-night stay at Waimea Plantation Cottages on Kauaʻi, a prize worth roughly $2,000 to $4,000 depending on where you fly from and when. We think that's a smart way to reward the readers who actually know these islands, and it's worth entering even if you'd vote anyway. Before you cast a ballot, spend some time with our guide to Discover Kauaʻi's Best Kept Secrets: Where Adventure Meets Island Luxury and our thoughts on How to Explore Kauaʻi With Respect for Its Resilient Communities. A vote is a small thing. Knowing what you're voting for is the point.
Here's the practical part. Register at vote.hawaiimagazine.com with an email address and submit at least one valid vote in any category. Registration alone doesn't count. You get one giveaway entry for the whole entry period, no matter how many categories you vote in or how many days you return, so there's no reason to game it. The entry period runs through December 20, 2026, at 11:59 p.m. Hawaiʻi Standard Time, and the winner is drawn at random from eligible registered voters within about 30 days after that. If you win, you'll have five business days to respond. Miss that window and an alternate gets pulled. Set a reminder now if you're the type who lets email pile up.
The prize itself is a good fit for the way we like to travel. Waimea Plantation Cottages sits on Kauaʻi's west side, away from the resort rush, and a four-night stay there pairs naturally with the slow, rooted kind of island experience we keep pointing readers toward. Read our piece on How to Visit Kauai's North Shore After the Floods with Respect and Awareness and you'll understand why we'd rather see a winner linger in one place than sprint between islands. Know what the prize doesn't cover: airfare taxes, baggage fees, meals, parking, ground transportation, gratuities and incidentals are on you, and the tickets and cottage come with blackout dates and booking restrictions. Budget for those before you start dreaming.
Our takeaway is simple: enter once, vote honestly, and treat the ballot as a chance to champion the places that made your own trips memorable. The businesses that top these categories get real attention from travelers planning their next visit, so your vote carries weight beyond the sweepstakes. Watch the December 20 deadline, and watch your inbox in January. The real question is whether the winner uses those four nights to explore or to finally slow down.