🎧 A “Free” Vacation That Took Us for a Ride

There’s a reason I now triple-check every “free vacation” offer.

Let me take you back to the moment my boyfriend and I thought we’d scored the deal of a lifetime — and how we ended up paying $836.50, surrendering over 12 hours of our lives, and being emotionally steamrolled by smooth-talking timeshare salespeople.

The worst part? We weren’t naïve — just hopeful. And that hope was weaponized.

📻 It All Started With a Radio Call…

We were huge fans of 99JAMZ Miami. One sunny day, the station ran a call-in giveaway: a “free” trip to Jamaica, Puerto Rico, or Mexico.

We called. We won. Cue the confetti, right?

Not quite.

The “free” trip came with a $99 non-refundable processing fee to “secure” our spot. A little red flag fluttered, but we figured hey — $99 for paradise? Still a deal.

But that $99 was just the cover charge for what became an expensive performance.

🎯 The Trap Tightens: Enter the Timeshare

To get our trip details, we had to drive 2 hours from the Florida Keys to Fort Lauderdale for a required “presentation.” It turned out to be a two-hour timeshare pitch with zero breaks and high-pressure tactics.

We weren’t travelers. We were targets.

The sales team wasn’t casually offering vacation options — they were trained manipulators, masters of manufacturing urgency. We were barely 10 minutes into their presentation when we were being asked to sign contracts for travel memberships costing thousands.

We declined. Firmly.

So they switched tactics: softer voices, a “supervisor” who just wanted to “chat,” and finally, the pivot — “All you need is a $199 deposit today to unlock your dream getaway.”

Already $159 deep (counting gas), we figured we’d come this far. Maybe it really would be worth it.

But that wasn’t the end.

🧾 Then Came the Fees

Weeks later, we were sent a list of “available” hotels — three options, all in Montego Bay, Jamaica. Once we selected one, we were hit with another demand: $478 in “agency fees, hotel taxes, and processing charges.”

We started to realize this wasn’t an opportunity. It was a funnel — carefully designed to keep extracting more from us at every step.

At that point, we were in for $836.50, not including time, stress, gas, or emotional damage. The cherry on top? We looked up the exact same trip online — including flights — and the total? $833.

No itemized invoice. No refund. No transparency. And zero accountability.

We never took the trip. We never got our money back. And we never listened to another giveaway on 99JAMZ again.

👎 We Weren’t Just Scammed — We Were Victimized

This wasn’t a one-time mistake. It was a well-oiled scheme that exploits people who just want a break — often those who can least afford the risk.

We weren’t dumb. We were hopeful. And we were manipulated.

They preyed on excitement, urgency, and the fear of missing out. And it’s happening to thousands of people every year.

So here’s what I wish someone had told me before I got trapped.

⚠️ How to Spot a Travel Scam Before It’s Too Late

1. If it sounds too good to be true, it is. That “free” trip will almost always cost more than planning your own on Expedia.
2. Never pay non-refundable “processing fees.” Reputable contests cover your prize fully. If you have to pay a dime to claim it, walk away.
3. Google the company’s name + “scam.” The reviews for GRCVO (the company behind our nightmare) are horrifying. We just didn’t think to look.
4. Beware of aggressive time limits. If they say “This deal is only good for today,” it’s a manipulation tactic. Real businesses let you think things over.
5. Report scams to the right agencies:

• FTC Complaint Assistant
• FCC
• Your State Attorney General

6. Trust your gut. If the salesperson feels off, if the details are murky, or if you feel pressured — walk away.

✅ Real Free Travel: No Gimmicks, Just Chicago

After licking our wounds, we did something radical: we focused on travel we could actually afford. And you know what? Chicago delivered more joy, beauty, and authentic memories — without the fine print or fake smiles.

Here are totally free, absolutely worth-it things to do in Chicago that I’d recommend 100 times over any radio “deal.”

🏛️ Top Free Things to Do in Chicago

1. Millennium Park See the iconic Bean (Cloud Gate), take selfies at Crown Fountain, and lay in the grass by the Jay Pritzker Pavilion. Bonus: Free concerts in summer!
2. Lincoln Park Zoo One of the last free zoos in the U.S. Great for families, couples, or solo travelers.
3. Chicago Cultural Center Gorgeous Tiffany glass domes, rotating art and architecture exhibits, and beautiful interiors.
4. The Lakefront Trail 18 miles of scenic shoreline views, beaches, sculptures, and skyline backdrops. Perfect for walkers, runners, and bikers.
5. Navy Pier Fireworks Catch dazzling displays every Wednesday and Saturday night in summer — visible from nearby beaches and parks, too.
6. Free Museum Days Major museums like the Art Institute, Field Museum, and Museum of Science and Industry offer free entry for Illinois residents on specific days.
7. Garfield Park Conservatory A lush indoor jungle that’s free to enter. Great for cold-weather travel or slow, mindful mornings.
8. Chicago Riverwalk Sip a coffee, admire the bridges, and enjoy public art installations as you stroll through downtown.
9. Chicago SummerDance + Movies in the Park Dance under the stars or catch a classic film on a blanket in Grant Park — all for free.
10. Neighborhood Street Festivals From Pilsen to Logan Square, Chicago’s summer weekends are full of free-entry festivals celebrating art, food, and culture.

🧱 Final Thoughts: From Scam to Sanity

We thought we’d found the ultimate travel hack — a free vacation that just needed a little faith.

Instead, we got scammed, stressed, and stuck with a bill.

But the journey taught us something far more valuable than any beachfront view:

If it requires manipulation to sell, it’s not worth your time or trust.

And more importantly — you don’t need trickery to travel well.

Cities like Chicago are full of rich culture, stunning sights, and joyful surprises that don’t cost a cent. All it takes is a curious heart and a little planning.

💬 Have You Been Burned By a Travel Scam?

You’re not alone — and you’re not stupid. These setups are designed to fool smart people.

If you’ve had a similar experience or found an actually amazing free travel opportunity, drop a comment below and help someone else steer clear of the traps.

Let’s travel smarter — and leave the scams in the dust.