Travel sweepstakes are seemingly everywhere, enticing you to enter to win trips to family destinations like Orlando, big cities like New York and exotic locales like Fiji. It’s fun to think about jetting off to somewhere you’ve only dreamed about. BUT, are travel sweepstakes really worth your time? Does anyone really win? Here’s a look at the pros and cons of travel sweepstakes.

Advantages to Traveling with Sweepstakes

There are some distinct advantages to winning a travel sweepstakes prize…

  • It’s fun. Who can put a dollar value on the thrill of learning that you just won a trip? You can’t buy that kind of excitement.
  • Your trip is planned for you…down to the last detail. Would you know how to begin planning a trip to Hong Kong or the Amazon? With a sweepstakes trip, you don’t have to make the arrangements. It’s all planned for you.
  • You often get to experience things regular travelers don’t see. One of the big advantages to a sweepstakes trip is that they often include features that you couldn’t buy at any price, such as a chance to attend a movie premiere, a visit to a winery or distillery that’s usually closed to the public, or the opportunity to meet a celebrity like Oprah Winfrey!
  • You are exposed to exotic destinations that you might not consider if not for the sweepstakes. Would you consider Iceland for your family vacation…or Panama…or Taos, New Mexico? Sweepstakes prizes allow you to expand your horizons to out-of-the-ordinary destinations.
  • It’s “free.” Well, sort of free (see the section about taxes below.) However, no matter what your tax rate, the trip will cost less than if you purchased it yourself.

Disadvantages to Using Sweepstakes to Fund Your Travel

Of course, there really is no such thing as a “free lunch.” There are a few downsides to winning a “free” trip. These include:

  • Taxes. US tax laws require sweepstakes winners to pay federal income taxes on all sweepstakes wins as if they have earned the money working. Sponsors are required to report any win valued at more than $600 to the IRS. To offset this, many prizes include cash as well as the prize (but, of course, the cash is taxed, too.)
  • Trips are usually non-transferable. Sweepstakes sponsors generally require that you take the trip yourself. Don’t count on being able to give it to your daughter for her honeymoon or your parents for a weekend getaway. Usually, you’re allowed to take at least one guest. Family-oriented prizes, like those to Walt Disney World, are often for four people.
  • Sweepstakes trips often have date restrictions. Sweepstakes trips, especially those that revolve around a special event, generally have to be taken within a specific time frame. In addition, trips are for a set period (for example, three or seven days), although some sponsors will let you extend the trip at your own expense.
  • The Scams. Unfortunately, travel scams abound and take advantage of our desire to win a “free” trip. In general, any trip sponsored by a recognizable company will be legit. Equally, any contest that asks you to buy something to enter–or that asks for your credit card number to enter–is a scam.

Can You Really Win?

In one word, YES. You can win. The Internet is full of stories about “ordinary” people winning trips all over the globe.’s contest site shares the story of one woman who won a three-day trip to Vail and of another woman who won a trip to Egypt. The sweepstakes site, tells of readers who have won trips to New York City and to any sporting event in the US.


Has anyone out there won a trip from a sweepstakes entry? If so, tell us about it by leaving a comment below.


Travel for "Free" by Entering Sweepstakes