We Won a Trip to Hawaii From a Sweepstakes, But Was It Really Free?

Last year, my wife and I were thrilled when we got a call saying we’d won a free trip to Maui, just for entering a contest at a Lakers game. The trip included airfare and hotel accommodations, though we’d have to cover mandatory taxes of about $150.

It sounded too good to be true … and it was.

What followed was an 11-month ordeal filled with deception, questionable practices, and endless frustration. Here’s how it unfolded.

Winning a Free Hawaii Trip From a Contest

In January 2024, we attended a Lakers game with my wife’s relatives who were visiting from Brazil. During halftime, we saw kiosks offering a chance to win a free trip by entering our information. A few weeks later, my wife received a call saying her name had been drawn.

We could choose from 5 destinations, but as soon as we heard “Maui,” our minds were made up. The trip wasn’t entirely free — we’d need to pay mandatory taxes — but we’d have a year to travel.

Everything sounded legitimate at first, though we started sensing red flags when the company made another call to ensure we would come to pick up our trip voucher. The agent offered to sweeten the deal with another voucher: 2 hotel nights near Lake Tahoe, though this wouldn’t include transportation.

To claim the vouchers, we had to schedule a Saturday appointment. Since we were leaving for Europe soon, we asked to set the appointment for the end of March. The agent said this wasn’t a problem and hung up after giving us a phone number to schedule our appointment when we were ready.

First Red Flags

After returning from our Europe trip, we scheduled the appointment for Saturday, March 29, 2024. Oddly, the agent wouldn’t provide the office’s address until the day before the meeting. Even stranger, the next day, I received a call claiming my name had also been drawn as a winner from the same contest. It was suspicious, but we still planned to go to the appointment we’d scheduled in my wife’s name.

On Friday, we got a reminder call for our Saturday appointment and finally received the address. A quick Google search of the location produced reviews calling it a “scam.” Determined to get our trip, we decided to proceed and communicate with each other in Portuguese so employees wouldn’t know what we were saying.

Surprise: It’s a Timeshare Presentation

Walking into the office, we immediately saw a giant Resorts Condominiums International sign. A receptionist confirmed it was a timeshare presentation. This was illegal under California law, which requires upfront disclosure of sales presentations.

The lobby was packed with others who had “won” trips — obviously not an exclusive prize. We were herded into a theater for what was supposed to be a 2-hour presentation. Technical difficulties delayed the video, so they moved straight to individual sales pitches.

When a sales agent began asking us questions, we tried to share as little info as possible. The agent launched into a pitch about timeshares, but when she tried to calculate how much we spend on travel, her confusion was clear. We told her about our recent 3-week European trip, where we used points and spent less than $250 on hotels. She was shocked when she realized we meant $250 for the whole trip.

The agent admitted we weren’t good prospects and offered to let us leave early. However, the receptionist wanted us to sign a form forfeiting the voucher for leaving early. After a heated exchange, staff begrudgingly handed over a trip voucher. We also made sure to get our parking validated on the way out.

Booking the Trip Was a Nightmare

The real trouble began after we received the voucher. To book, we had to send a money order for the taxes and choose 3 potential travel dates. We planned for a 1-week Maui trip, using their 2 free hotel nights and covering another 5 nights ourselves. Multiple employees had told us staying extra nights by booking our own hotel wouldn’t be a problem, so long as we understood that only the flights and 2 hotel nights were included in our voucher.

Initially, things seemed fine. A week after mailing the voucher, we confirmed January 20, 2025, as our travel date.

But over the ensuing 9 months, communication became a mess. The company we were dealing with, Casablanca Express, made everything as difficult as possible.

Charter Flights and Upselling

In late November, we got a call from an agent named Jonathan. He explained the itinerary: a 13-hour, 2-stop flight from Los Angeles to Maui, arriving at 11 p.m. and departing at 6 a.m. 2 days later. This essentially gave us just 1 day in Maui — surprising when flights from LAX to Maui take just 6 hours.

When we asked about extending the trip as planned, Jonathan claimed it would cost us an extra $1,800. He became combative when we questioned this and eventually hung up, saying he didn’t want to deal with us.

We called back and spoke to Julio, a supervisor, who promised to review recordings of our previous calls. He seemed sympathetic, but we still faced endless roadblocks. It felt like the company was trying to discourage us from taking the trip. We got the impression that staff were instructed not to talk to us. No one would call us back, and receptionists always put us on hold as soon as they realized who we were — or simply hung up.

How We (Finally) Booked the Trip

One of the numerous employee voicemails we encountered mentioned an email address. I sent an email, and the response said our trip was confirmed as we’d just spoken to someone a few days prior — a call that had never happened. As this was the week between Christmas and New Year, we were told that no booking agents would be available until January 6, 2025 — 2 weeks before our travel date.

On January 5, I sent an email reminding them to please call us on January 6 to book our trip. I also called on Monday, January 6, saying we were ready to book our trip — departing in 14 days. The receptionist said we’d get a confirmation call by the end of the week and then hung up.

By Thursday, we had nothing. We’d booked our other 5 hotel nights and had given up on the 13-hour flight itinerary, booking our own flights to Maui using points — something that saved the travel agency money. I called again since we were supposed to depart in 11 days.

Imagine my surprise when Julio answered my call to the 800 number on Thursday. I recognized his voice immediately. With the Los Angeles wildfires, the receptionist was out. I mentioned my countless voicemails, and he said he’d been “busy” for the past several weeks. I told him we simply wanted to confirm our 2 hotel nights. He promised to call with hotel details by the end of the day. Politely, I told him I didn’t have much faith in that after countless broken promises.

To his credit, Julio called me while driving home that day. He said we could stay at the Maui Beach Hotel near Kahului Airport (OGG). We pointed out that we weren’t taking their flights, saving them money, and asked if we could stay closer to Ka’anapali or Wailea.

Julio promised that a booking agent would contact us the next morning with hotel options and that we would get everything confirmed “tomorrow.” Since this call had come from Julio’s cell phone, I actually believed it this time.

Patricia was the first person from Casablanca Express who got straight to business and fulfilled promises. She told me to go to a hotel’s website, look up its location and rooms, and see if we liked it. If not, she could suggest 2 more.

The first hotel was agreeable to us, and we were happy to accept it so we could finally confirm everything. An hour later, we got a confirmation email for 2 nights at the Maui Coast Hotel in Kihei. Patricia informed us of a $46 daily resort fee to pay at check-in. That covered things like complimentary bike usage and parking, though it didn’t include breakfast.

What Our Hotel Was Like

Arriving at the hotel, we were nervous about potential problems. Luckily, we were wrong. The hotel quickly found the reservation in my wife’s name, and the desk agent didn’t ask for any payment beyond the resort fee.

While it wouldn’t win any awards for luxury, the Maui Coast Hotel was better than we expected. It offered a complimentary shuttle around Kihei, had both freshwater and saltwater pools, a nice poolside bar, and a great gym.

The hotel met our basic needs, and its location — walkable to beaches, shops, restaurants, and bars — was our favorite feature. We didn’t have any issues with the Maui Coast Hotel staff. As far as we can tell, they weren’t involved in our frustrations with Casablanca Express.

Final Thoughts

In hindsight, the trip wasn’t worth the effort it required. However, it served as a valuable lesson in recognizing and avoiding predatory schemes. If you’re ever offered a “free trip,” proceed with extreme caution. Ask questions and decide how much effort the trip is worth. Then be persistent.

Now that the trip is over, we’ll be filing complaints with the state government, Better Business Bureau, and Crypto.com Arena to let them know what this company is doing in their arena. When we didn’t buy a timeshare and dared to ask questions about our holiday, it felt like Casablanca Express tried its hardest to not give us the promised trip.