>>> "I won a spring break trip to Florida in a bar raffle when I was in college. When I went to collect it, I learned it was a bus ticket to Florida (from Detroit, so two days of driving), a presumably crappy hotel, but the worst was that it was a trip for one. If I wanted to go, I'd have to convince someone to purchase another ticket. 'Oh, please sit on a Greyhound with me and 50 other crazy spring breakers for two days on our way to the cockroach motel...'"
>>> "I won a trip to Las Vegas on a Price Is Right Live show. Had the option to take the trip (worth $1,200) 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."
>>> "I won a radio call-in trip for a nine-day stay in Australia. On top of that, we flew on a fancy plane with the band Jet, got free tickets to a music festival, and got a private concert/hang out session with Jet. Free hotel stays 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. I had to look everyone in the eye and tell them I just called into the radio and won."
>>> "I was living in Miami at the time, back in 1999.
My girlfriend, without my knowledge, dropped two postcards in the mail, one with her name and one with mine, to 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, so basically they would pick 200 winners from each city and fly them and a guest in.
I am checking the mail one day and there's this huge 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 out.
'We won!' she cried.
'Won what?' I asked.
Then she lets me in how she was reading the paper and doing laundry while I was at work, 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.
I open the envelope, which informs me I have indeed won a trip for two to New York. All expenses paid. I go to work the next day and inform my boss that I need Thursday and Friday off and that I won a trip. My 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 strutting down the hallway, envelope in hand, and I see Robert. Robert sees my grin, and then looks down at my envelope and becomes LIVID!
'What 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 MOLY SO DID I!!'
We live in Miami. Miami is huge. Only 200 people win. We worked at a place with maybe 30 people. Two winners from the same company and he was 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. Four 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 on 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 Ramen Noodle bowl in all its glory. I go to open the window, 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 going to 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 two minutes in real-time, and they're back on it. The whole thing wrapped in little more than an hour.
The 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 $50s. 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 large 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 awesome. We meander 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."
>>> "Towards the end of her life (pretty much housebound due to COPD), my very intelligent mother started entering competitions online to keep her brain active as her body deteriorated. And she would win little bits here and there: a CD, a bottle of perfume, some DVDs, etc. Then one day she got an email from The Guardian newspaper telling her she had won one of five top prizes in a holiday competition -- winning a £10,000 two-week trip to Peru. Everything was included, a full itinerary tour, bed and breakfast accommodation in four-star hotels, and all flights and transfers. Cue excitement and joy before she eventually came to terms with the fact that she was far too sick to go. She was on piped oxygen in the house, so going somewhere where oxygen is thin was a really bad idea. They were very nice and offered her basically any alternative up to the same cost, but no one would insure her to go anywhere and she came to the realization that she would never travel anywhere again. She gave the holiday to me. I ended up going with a mate, and it was a great holiday. But the whole time I felt guilty that I was going and not her. We made sure to bring back lots and lots of presents. She died about six months later."
>>> "I won a radio contest in Chicago for having an ugly tattoo. The prize was free removal. I didn't go through with it because the taxes were going to be around $1,200, and I would have had to drive over an hour to the clinic where it was estimated to need seven sessions. I'd rather spend that much money on a cover-up and get something that I'd like."
>>> "My friend won a trip to meet Bam Margera. As the date approached, the '$3,000' trip was only us getting our lodging and our meals are taken care of in suburban Philadelphia. A friend's uncle, who was a lawyer, raised a real stink about it, so they flew us to LA instead and paid for everything. The trip was great, but since I was a teenager at the time, I imagine it could have been better. Also, Bam was a jerk. Never said two words to us. Simply talked to the guy who ran the competition the whole time. Worth the story though."
>>> "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 Jonas Brothers concert."
>>> "My parents won an all-inclusive trip to see the Toronto Blue Jays play the Boston Red Sox back in the early '90s. 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, realizes 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 enjoyed a true all-expense paid trip. I don't remember much more than that because I was like seven at the time. We do love to bring it up every once and a while, just to tease mom."
>>> "It was a radio contest in Canada. My mom won an all expenses paid trip to Disneyland for four. We got flights, four nights in a Disney hotel at the park, three days worth of park passes, $500 Disney cash, and a voucher for one free theme breakfast and one free theme dinner. Trip cost maybe $500 out of pocket, so 10/10 would do again."
>>> "My grandma bought lottery tickets all her life, and the running gag was that she kept winning free tickets. One day she scratched the three TV contest logos, which meant her name was in the box for the end of the season shows where they'd pick through these people to have enough contestants for the season. Anyway, she got sick that year, she was 92, so when they finally picked her name, she asked my mother to go for her. We went with my mom, we had a night at the hotel plus dinner and breakfast. Mind you we already live in the city, but it was a cool night. Then we went to the TV station and sat in the crowd, while my mother went live. She ended up winning $30,000 in cash. It was originally less, but she also won two travel vouchers that she exchanged for money. My grandmother died that year, but at least she got the best services as my parents and uncle were able to pay for it all with the winning money. It's almost as if someone up there decided my grandma had lived in poverty all of her life, so at least she left us while being comfortable. It all went smoothly."
>>> "I won 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 timeshare in Panama City on the dirtiest part of the beach, and that's saying something. And I don't mean seaweed and sea stuff washed ashore, I mean, like, drink cans and fast food bags next to dirty diapers. It was bad. Secondly, they didn't even pay for travel, which was fine because we lived in Georgia so it wasn't that bad, but they did pay for 'one five-star dinner' and it was some tourist trap Florida authentic seafood place. The seafood was crap, and the atmosphere was annoying, and if you traveled 15 minutes down the road, you'd find the same restaurant with a different name. I spent maybe $600 on food and a dolphin tour, which was fun. At least I got three days off work and free lodging."
>>> "I won a trip to Rottnest (a small island off the coast of Western Australia), and when I turned up for the ferry, they told me the tickets were fake."
>>> "I won an all expense paid vacation to the Poconos when I was on a game show called Pick Your Brain as a fifth-grader back in the '90s. This place was not the place where a kid could readily have fun. The ad for the resort said, 'The Honeymoon Capital of the US' and our room also had a mirror on the ceiling. All the food was cruise ship style, which meant you had a set breakfast, lunch and dinner time each with a set menu that you could order off of, and 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 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 2 and 4 p.m.). 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."
>>> "I was on Wheel of Fortune back in 2007. 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. So by forfeiting that trip, I got $500 back in taxes, which was nice.
But I did take the trip to Hawaii. I was put up in the Hilton Waikoloa Village, which was amazing. They gave me $1,000 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, and it helped cover his expenses too.
I rented snorkeling gear to swim with sea turtles. It was awesome and this one turtle was super playful, which was apparently 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 flipper high-fived 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. I went up to an outdoor bar and the bartender asked where I was from, and I told him Wisconsin.
'WISCONSIN! You need to try this!' And I had my first longboard from a tap. It won my approval because it was hot as soup outside and the drink 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.
One 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 canceled 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."
>>> "I won a trip to Vermont on some Nickelodeon game show. They only offered extremely specific dates that were super inconvenient for 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."
>>> "I won a trip for two to Maui on Wheel of Fortune. 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, drinks 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."
>>> "I won a trip to the Bahamas on a cruise ship from a radio station. My husband had quit working at that radio station only three months before, and if he still worked there, I wouldn't have been allowed to win. I found out it was my mom who actually entered my name into the 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 were, but it wasn't 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 contests like I did, or being the top sellers of the product in their area, or who were bigwigs in the industry. I was shocked at how many people were complaining about the slightest things on the trip. Like, why are you complaining? You are not paying anything to take the trip. Talk about being spoiled."
>>> "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 whatever game or activity I wanted, and everything was open (as far as I was concerned) all the time. In addition to that, Radio Disney selected 10 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. 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."
>>> "This was a competition via Twitter. I won a trip to New York from the UK for two people. It was round-trip flights from Heathrow to JFK; a two-night stay in a four-star hotel; airport transfers; £500 spending money; a helicopter flight; and tickets to a Broadway show of our choice. Due to flight timings, we ended up using some of the spending money to pay for a 3rd night at the hotel. The trip was everything I'd hoped and more. I'd always wanted to go to New York, and it didn't disappoint. The helicopter flight was a massive highlight, and we went to see the Lion King, which was also amazing! We used some of our own savings, so we had plenty of spending money for a once in a lifetime trip. I would recommend you enter random competitions on Twitter!"
>>> "I won a trip to the Super Bowl in New York from Gillette via Twitter. It was about two weeks before the Super Bowl and at first, I thought it was a hoax, but my daughter won and took me along. Everything was first class, the hotel was the JW Marriott Time Square and was loaded with football players (current and former). Plus all the Super Bowl NFL stuff was happening right there. A pregame show at the stadium included The Band Perry, all the food and drinks we wanted, an open bar, and stars. We got a free bus transfer from the hotel to the stadium and first row 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. I will never shave with anything but Gillette ever again."