Sweepstakes To Scams: What Changed With Free Hawaii Trips

For years, Beat of Hawaii was the place to find Hawaii travel sweepstakes. We posted dozens annually. Most came from well-known companies, including airlines, hotel chains, credit card companies, and travel brands. They weren’t just fluff. At least two of our readers, whom we are aware of, won trips from those contests, including one who sent photos after landing a $12,000 Maui vacation. It wasn’t unusual back then. It was exciting, and it was real.

That era slowly faded after COVID. Not because of one defining scam or single bad contest, but because something quieter happened. The good ones disappeared. The odds stretched. The fine print and the resulting spam emails grew. People got suspicious—or just stopped caring. Eventually, we did too.

The golden age of Hawaii sweepstakes.

Back then, many contests were simple. Enter your email address and, optionally, your mailing address, and wait. Even back then, it was recommended to use a separate inbox to deal with the spam, which tells you something in and of itself. Still, it often felt like a fair trade for the real chance at a dream trip. Companies like REI, Coca-Cola, Hawaiian Airlines, and Hilton were all involved. You could dream a little. And once in a while, someone won.

Eventually, though, the questions slowed. Even now, several Hawaii sweepstakes still float around. But they’re mostly ignored. Even the real ones no longer gain traction. The energy is gone. It’s not just about odds—it’s about trust. Something shifted.

Sweepstakes scam touches Hawaii.

Just recently, a Hawaii resident lost more than $50,000 after responding to a fake sweepstakes letter. It looked official and came by mail. The instructions? Wire money to pay taxes and claim your prize. That was all it took.

In a real sweepstakes, if you win a prize valued at $600 or more, the sponsor is required to report it to the IRS using Form 1099-MISC. The value of the award is treated as ordinary income, and you report it on your tax return the following year.

If someone says you need to pay taxes before receiving your prize, that’s a red flag. That’s not how legitimate sweepstakes work.

Why Beat of Hawaii pulled the plug on sweepstakes.

The contests didn’t turn into scams, exactly—but the space around them got blurry. We began to see promotions with confusing conditions, limitations, and exclusions, unfamiliar sponsors, and entry forms that felt more like data collection exercises than anything else.

Even writing about them became arduous. Some campaigns were barely more than thinly disguised marketing tools. Others were for trips that featured either airfare with no hotel, or hotel with no airfare. Really? And some routed users through third-party lists or added them to aggressive promotional pipelines. And then some pushed entrants straight into timeshare lead funnels.

We continued to monitor cautiously for a while, sharing only the sweepstakes that still looked solid. And when we did, we tried to share all the limitations and workarounds. But year by year, the fun faded both for you and for us. Reader engagement slowed. Then it stopped. So we did, too.

Some readers were disappointed. We heard from those who felt misled when contests had already gone offline or had fine print that made it all but impossible to figure out how to enter. That kind of feedback told us the magic was fading and the frustration growing.

The rise of scams and digital risks.

We’re not saying sweepstakes caused the scams. However, the format—win a trip, provide your information, act quickly—was too easy for fraudsters to exploit. First, it was spam calls and mailers. Then it shifted online. Fake websites. Spoofed brand pages. Misleading travel booking forms. We even heard from one of our friends who booked through what appeared to be a legitimate site, only to have their credit card drained days later. It didn’t feel like a mistake—it felt like a trap.

To make matters worse, Hawaiian Airlines was hit by a cyberattack around the same time as the $50,000 scam. That had absolutely nothing to do with sweepstakes, but it said something bigger. Even the most trusted names in Hawaii travel are vulnerable now. If airline systems can be breached, it’s not hard to see why people hesitate to click on a trip offer.

How to spot Hawaii sweepstakes scams.

We’ve followed this long enough to know what raises red flags. Start with the URL. If the link looks off or doesn’t match the company it claims to be from, close the tab. Just because it says Hawaii doesn’t mean it’s real.

-HTTPS is a start, but it isn’t proof. All it means is that the site has a basic security certificate—it doesn’t mean the site is legitimate, safe, or who it claims to be. Scammers use HTTPS, too. What matters more is whether the domain matches the brand, and whether you found the link through a trusted source, not from a random email or ad.

-Never wire money. Never pay to claim a prize. If a sweepstakes asks for your credit card—even to verify your identity—it’s time to back out. That’s not how real contests work, and it never was.

-Do not pay taxes upfront.

-If the offer isn’t mentioned anywhere on the official website of the brand running it, treat it as fake until proven otherwise. No legitimate company hides a real giveaway. A free trip to Hawaii should never begin by asking for inappropriate information or your money.

The future of Hawaii sweepstakes on Beat of Hawaii.

We haven’t ruled them out entirely. If something real comes along—easy to enter, clear about the rules, and from a name we recognize—we’ll take a look. But it’s been a long time since we’ve seen one that felt worth your time, let alone ours. We won’t share promotions to fill space.

Lead photo of Disney Aulani Resort. When that hotel was included, they became some of the most popular contests we ever published.

Plenty of readers used to ask when the next contests were coming. Now, no one does. That probably tells us what we need to know. What’s your take on free Hawaii sweepstakes?