18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

There are few things in this silly world more exciting than winning something big. Be it from a radio contest, sweepstakes, or even game show, it must be absolutely thrilling to be the lucky recipient of an all-expenses paid trip to some exotic destination that would have otherwise cost thousands of dollars.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

But are those trips actually any good? Some real-life trip winners recently got on Reddit to share with all of us non-winners about how that fabulous vacation really went.

1. This trip that catpirate won was all-inclusive with everything except birth control.

I won a 7 night/8 day vacation to a sandals resort in the Bahamas. Everything was included, all we had to pay for was a dinner on the dock during the sunset for $100 that we wanted to do for our wedding anniversary. Trip was amazing and we came home with a permanent souvenir...my son :)

2. Being on an old Nickelodeon game show was prize enough for cirquedugumby, sadly.

I won a trip to Vermont on some Nickelodeon game show. They only offered extremely specific dates that were super inconvenient to anyone. Given that I was in high school and couldn't just fly off to a cabin on a Wednesday-Friday getaway, the prize expired a year later.


3. User yinzerman won a trip to Maui and it sounds AW_S_M_.

I won a trip for two to Maui on Wheel of Fortune. I'm a redditor, so I don't have a girlfriend and therefore took my brother. Imagine a hotel pool with a sea of honeymooners, diamond rings newly glistening in the tropical sunlight, then out of nowhere come two fat, squelching idiots, pina coladas in chubby hands, splashing and wrestling, having contests to see who could jump farther off the diving board without spilling their drink, judging each other not only on spillage but also distance and style. It was a fantastic trip.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

4. It was a dream come true for capt_argyle, except for the parts about needing a lawyer and a celebrity acting like a jerk.

My friend won a trip to meet Bam Margera. As the date approached, the "$3000" trip was only us getting our lodging and our meals taken care of.... in suburban Philadelphia.

Friends uncle, a lawyer, raised a real stink about it, so they flew us to LA instead and paid for everything.

Trip was great, but since I was a teenager at the time, I imagine it could have been better.

Also, Bam was an ass. Never said two words to us. Simply talked to the guy who ran the competition the whole time. Worth the story though...


5. The trip won by omahaspeedster is the best a man can get.

Won a Trip to the Super Bowl in New York from Gillette via twitter. It was about 2 weeks before the Super Bowl, at first I thought it was a hoax but my daughter won and took me along. Every thing was First Class, Hotel (JW Marriott Time Square, place was loaded with players current and ex. Plus all the super Bowl NFL stuff was happening right there), Pregame at the Stadium included The Band Perry, all the food and drinks we wanted open bar and stars in the pre-game tailgate. Bus transfer from Hotel to Stadium, flights and Row 1 seats near the Seahawks bench, we were sitting in front of players wives, girlfriends and friends, they carried the super Bowl trophy right past us and the sideline was full of stars. Everything was first class, I will never shave with anything but Gillette ever again.


6. This story from jimbonics is long, but it is wonderful, magical, and will make you really miss David Letterman.

Not a game show, but...

Was living in Miami at the time, 1999.

My girlfriend, without my knowledge, dropped two postcards in the mail, one with her name and one with mine, to the The Late Show with David Letterman. They had a week planned where each nights' taping was themed around a certain city, while still being filmed at the Ed Sullivan Theater.

The theater only seats around 400 people. Basically they would pick 200 winners from each city and fly them and a guest in.

So again, knowing nothing about this, I'm checking the mail one day and there's this huge 8 1/2 x 11 envelope with the Letterman logo with my name on it. I show it to my girlfriend with a quizzical look on my face and she starts flipping the fuck out.

"OMGOMGOMG we won!!"

"Won what??"

Then she lets me in how she was reading the paper one Saturday doing laundry while I was at work and came across the Ad from Letterman, and sent in a couple of postcards. She didn't tell me about it because she didn't want to jinx it.

Sure as shit, I open the envelope, which informs me I have indeed won a trip for two to NYNY. All expenses paid, etc.

I go into work the next day, and inform my boss that I need Thursday and Friday off, won a fucking trip, etc.

Boss tells me, "You should go back into the sales area and talk to Robert."

It was weird, but Robert was a friend, so whatever.

So I'm kinda struttin' down the hallway, envelope in hand, and I see Robert. Robert sees my shit-eating grin, and then looks down at my envelope and gets PISSED!

"What the hell are you doing rummaging around my desk? Put that back where you found it!!"

I'm like, "Dude. This is mine. I won a trip to Letterman."

He looks at me wild-eyed and goes "HOLY SHIT SO DID I!!"

Keep this in mind: We live in Miami. Miami is fucking huge. Only 200 people win. We worked at a place with maybe 30 people. 2 winners from the same company, and he was about the only friend I had made in my short time living in Miami. Unreal.

The Thursday we are to travel rolls around, and the 400 of us gather at the airport. 4 privately-chartered, medium-sized jets ferry us non-stop from Miami to New York. Easily the best air travel experience I've ever had. We get off at the tarmac into these huge plush buses, and they drive us to the Sheraton on 52nd Street, Times Square.

We check in, and go up to our room, around the 30th floor or so. I open the curtains, and BAM, there's the big-ass Ramen Noodle bowl in all its glory. I go to open the window, but it only opened an inch, with one of those safety locks in place. So I closed the window, and with much more force, opened it again. Lock falls by the wayside, and now I have a fully opened window looking directly down on Times Square with a wonderful breeze. It was a gorgeous day and sight.

Next we go downstairs to meet with everyone, as they were feeding us and giving us our tickets to the taping. I got to shake hands with Forrest DeCalvert aka Larry Bud Melman.

Inside each envelope with the tickets was a crisp, new $50 bill. Turns out it was cheaper for them to pay us, taxes-wise.

Dinner is over and now we get to walk to the theater a couple blocks away. Cops had cordoned off the roads so 400 people could cross safely.

We get inside the theater, and it is every bit as cold as the stories say (so the audience wouldn't fall asleep, Ed Sullivan joked). Dave comes out just before the taping, explains a little how it's gonna go, asks us a couple of questions, gets a couple funny/quirky responses, seems satisfied that he got a little material to work with and says he'll be back out soon, ready to roll!

The guests were Glen Close, George Hamilton, and music by Elvis Crespo. Really cool. When they go to commercial break, it lasts 2 minutes in real-time, and they're back on it. The whole thing wrapped in like an hour and 10 minutes.

Interesting note, they used to do two tapings on Thursday, with the later taping being for Friday. They didn't work on Friday. So our Thursday night taping was actually for the next night.

Taping is over, and the production staff starts handing out these awesome Letterman-logo-stitched backpacks with goodies inside like hats, t-shirts, double-decker bus tour, etc.

We meet up with Robert and his girl, and the four of us go bar-hopping through Times Square with our crisp $50's. Thanks Dave!

The next day we get on the tour bus, and hop off at Empire State, and go to the top. You really get a feel for how insanely VAST New York City is from up there. Grids of buildings as far as the eye can see in nearly every direction.

The bus is long gone at this point, so we walk from Empire to Central Park, which is equally bad-ass. Trip around there for a while and walk back to our hotel. Buses pick us up, take us to the airport, and we fly home.

A whirlwind 24-hour trip to New York City, courtesy of David Letterman. We barely spent any money.

I had never been before, and I haven't been since.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

7. User dano_bannano put the brakes on a Vegas getaway.

I won a trip to Las Vegas on a Price Is Right Live show. Had the option to take the trip (worth $1200) or take smaller cash prize (i think $700) right away. I decided to take the trip as I had never been to Vegas. The company that put on the show contacted me about a week later to talk to me about it. I told them I wasn't sure when I wanted to go and I would contact them when I knew. A couple of weeks after that they sent me a check for the full amount of the trip with a note saying that I can book my trip whenever I want. I ended up getting tires and brakes for my car instead.


8. Tbjkbe didn't think she worked as hard for her cruise as other people did, like just having had a baby didn't make her deserving enough.

I won a trip to the Bahamas on a cruise ship of a radio station. Funny was my husband had quit that radio station only 3 months before or I wouldn't have been allowed to win. Found out it was my mom who actually entered my name in a 7UP drawing. I had just given birth to my daughter a few months before so my Mom and I went together while my husband stayed home with our daughter and older son.

It was wonderful and great and we were able to do a lot of sightseeing. Everything was paid, including all tips. I am not sure I remember how much the taxes where but is wasnt bad at all considering the total cost of the trip.

The only issue I had was the entire cruise was filled with people who won the trip by either winning contest like I did or being the top sellers of the product in their area or who where big wigs in the industry. I was shocked at how many people where complaining over the slightest things on the trip thinking why are you complaining? You are not paying anything to take the trip. ...talk about being spoiled.


9. Trollitical won the typical Spring Break experience.

I did win a three day trip to Florida for two from a radio show and let me tell you... It sucked.

First, the "condo" we won was straight up a hotel room looking time share in Panama City on the dirtiest part of the beach in Panama City, and that's saying something. And I don't mean seaweed and sea stuff washed ashore I mean like, beer cans and fast food bags next to dirty diaper bad.

Secondly, they didn't even pay for travel, which was fine we lived in Georgia so it wasn't that bad.. but they did pay for "one night five star dinner" and it was some tourist trap Florida authentic seafood place where the seafood was crap and the atmosphere was annoying and if traveled 15 minutes down the road you'd find the SAME restaurant with a different name.

I spent maybe 600 dollars on food and a dolphin tour which was fun. Overall I'd rate it a 7/10 cause three days off work and at least we got free lodging.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

10. Sounds pretty suite, acrosstheaeons.

I won a trip for two to a convention once. It was pretty sweet. They paid for airfare from east to west coast, put us up in Embassy Suites which was about a mile walk from the convention center, and got us tickets into the con itself. They didn't bother to put our names on the badges and the taxes sucked (they did warn us that we would owe taxes, but they didn't really explain the VALUE of what we would be paying taxes on until we got the tax form)


11. It's a troubling possibility that life may have peaked for beagoodbear at age 9.

Not a game show, but I won a vacation to the Beaches resort in Jamaica from Radio Disney when I was 9 years old.

The vacation was AWESOME. My family had never stayed at an all-inclusive resort before, so as a kid, I thought that I was in Heaven. They had awesome food, I could just join into whatever game or activity I wanted to, and everything was open (as far as I was concerned) all the time. In addition to that, Radio Disney selected ten winners for this trip and had a day where all 10 of us and our families got to participate in special 'VIP' events, including a private concert with Jesse McCartney. My little-kid mind was totally blown. It was the trip of a lifetime and I'll never forget it.

We (my parents) were responsible for the income tax for this trip, but it was still a way better deal than paying for the trip outright.


12. The in-laws of FWD_Me_Your_PMs still play "Plinko" three times a week (wink-wink).

My wife was conceived on a cruise that my in-laws won on The Price is Right, so I figure they had a pretty good time.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

13. OMG, dawrina got to visit Pixar.

I won a 3-day trip to San Francisco with an exclusive tour of Pixar and lunch with the directors and artists of Brave.

At first I was skeptical. They called me and told me I won and asked for my email to set up the entire affair. But to my utter surprise it turned out to be 100% genuine. I got free roundtrip airfare, a stay in a super swanky hotel in downtown San Francisco, a car rental, and the tour with the lunch.

The tour was only 1 day, so the other 2 days I spent exploring SanFran with my mom and seeing the sights. We went on a boat tour, saw the bridge close up, saw the redwood trees, went to fisherman's warf.

It was wickedly awesome 10/10 experience. One of the best vacations I have ever been on. Especially I would Never be able to afford to go out to California.


14. All in all, it was a pretty great trip for userbelowisamonster. Well, except for all the diarrhea.

I was on Wheel of Fortune back in 2007. The show recorded in 2006, and aired in 2007 anyway...

During the show I won a trip to Hawaii and a trip to London.

I had to forfeit the trip to London due to not getting a passport in time (traveling for work and the time it would have taken for me to get the time off, the passport, and get it organized was becoming a nightmare.)

So by forfeiting that trip I got $500 back in taxes, which was nice.

I did take the trip to Hawaii. I was put up in the Hilton Waikoloa Village which was amazing.

They gave me $1000 in spending money which I used for a rental car, food, drinks, and some souvenirs. My brother was the guest I got to bring with me so it helped cover his expenses too.

I rented snorkeling gear to swim with sea turtles. What's awesome is that this one turtle was super playful which was rare. It followed me around and it let me pet its shell without freaking out. At one point I went full on Disney princess and reached out my hand and his lil flipper slapped it. Just a totally surreal experience. I got out of the water and read a sign saying that messing with the sea turtles could result in big fines.....whoops....

Later I remember walking in Kona and it being 85 degrees and walking up to an outdoor bar. The bartender asked where I was from and I told him, "Wisconsin"

"BEER COUNTRY! You need to try this!" And I had my first longboard from tap. It won my approval because it was hot as soup outside and the beer was so cold...I had three!

Most of the time I stayed near my hotel room on the beach and just enjoyed having nowhere to be and all the time to get there.

Except when I crapped my pants. Like full blown king kamehameha crapped my pants...

Went to get some coffee and then sat and enjoyed it. In my way walking back to the room the urge to poop hit. I went from fast walking, to a full on sprint, to doing the penguin waddle. Eventually made it back to the room to find...

My brother was already on the toilet and refused to wrap it up. So after arguing through the door and looking at the trash can like it needed to pay for its sins and bolting for the public restroom at the beach.

I got halfway there when disaster struck and Hawaii got hit by another poonami.

I did the cowboy walk of shame into the stall and figured I would rinse everything off in the toilet and then just book it back to my room except a bunch of Hilton staff and lovely girls were walking by and even though they seemed oblivious I knew that they telepathically knew what I had done.

I ended up ditching my underpants in the trash bin and when I heard nothing I booked it back to the room, key in hand, and threw all my crappy pants in a plastic bag to take to the laundromat after I showered and changed.

The next day we went to the other side of the big island and checked out the volcano. That was pretty sweet!

On our last day we found that our plane was cancelled and they put us up in a hotel with a changed flight for the morning. So we got a free night in Hawaii.

All in all it was a lot of fun, and the islands are calling my name again. My wife and I are planning our 15th wedding anniversary and Hawaii is where we really want to go!


15. Sorry, sithacquisitor, but saying no-no to the JoBros is no-no numero uno.

My wife won a trip to Barbados through a radio show. Went with 40 other people who also won the same contest. All expenses paid, meals and drinks were covered. The only catch was a mandatory Shaggy and Jonas Brother concert.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.

16. Brett_Hulls_Foot's parents had a (base)ball.

my parents won an all inclusive trip to see the Toronto Blue Jays play the Boston Red Sox back in the early '90's.

It was some sort of draw and when they told my mom she won she didn't believe them. So they sent a package (flights from Toronto to Boston, hotel info, Game tickets, it was a 4 day stay) and she thought it was a scam so she threw it out!

A few days later they called and said hey your trip is next week, have you booked anything? She freaks out (realizing it's not a scam) and eventually finds the trip package in the trash.

They end up going, had a great long weekend touring Boston and enjoy a true all expenses paid trip. I don't remember much more than that, because I was like 7 at the time. We do love to bring it up every once and a while, just to tease mom.


17. PoisonRamune went to one of those Dirty Dancing places, but it ended up being more like Dirty Dancing: Havana Nights (i.e., not as good).

Won an all expense paid vacation to the Poconos when I was in the 5th grade (was on a game show called Pick Your Brain back in the 90s). This place was not the place where a kid going from 5th grade onto 6th grade could readily have fun (the ad for the resort said "The Honeymoon Capital of the US"), our room also had a mirror on the ceiling (so that was the educational part of my trip was learning why that was there). All the food was cruise ship style (you had a set breakfast, lunch and dinner time each with a set menu that you could order off of), the food was also pretty whatever (I distinctly remember really hating their roast beef meal). Days were spent either by the pool (which was always fucking crowded in a not fun way) or participating in their daily activities (once again like a cruise ship they had designated activities time like: bingo in the cafe between 2pm and 4pm). All in all it wasn't bad just a very sort of "factory type" vacation experience. However, I think my folks enjoyed the trip more than I did so I always considered it like a gift I won for them. 4/7 would go again... Actually, because I'm older I probably would goto something like that just to get the shit outta town for a bit.


18. Nukemm33 and family just keep on winning!

I won a radio call in trip for a 9 day stay in Australia. On top of that, we flew on the newly commisioned virgin blue airlines with the band Jet, got free tickets to the home bake festival, and got a private concert/hang out session with the band Jet. Free hotel stay as well.

The only downside is that when the winners were asked how they got the tickets, most of them had some hardship story about taking care of a handicapped loved one for all their lives, or an essay they wrote to win...and I had to look everyone in the eye and tell them I just called into the radio and won.

Bonus info: My daughter was conceived on this trip (broken condom...not her name but the event that happened...) And my wife ended up winning 2nd place in a pregnant bikini contest for the same radio station and we told this story during the contest.

18 lucky jerks who won a 'dream vacation' sweepstakes explain how it actually worked out.