On Christmas Eve, Visions of Free. Trips, That Is

It’s Christmas eve morning, and in place of sugar plums, I’m dreaming of free. Free trips, that is.

I’ve always been a secret fan of travel sweepstakes. You know the kind of thing: Enter for a chance to win an all-expense-paid luxe vacation on a jewel-like island in the South Pacific. Visions of swaying palms and fruity rum drinks, the air rich with coconut-scented sun lotion.

And did I mention free?

I’ve entered many such sweepstakes, never with any great expectations of actually winning. I’m a realist, and I know the odds are stacked against me. But I suppose my psychoanalyst would smirk knowingly and point out that such behavior must be driven by some deep seed of hope.

The word “free” comes to mind.

As anyone who participates in a frequent flyer program knows—or would know, if they listened to my shrink—travel is aspirational. It’s not just a trip, it’s a journey into the unknown. Romance and adventure await. And gambling on a chance to win something so ripe with possibility is hugely compelling.

Did I mention free?

If “free trips” resonates with you, here are two travel sweepstakes that are worth your while.

The first is from American Eagle, which is deploying a sweepstakes to publicize its 25th anniversary. Enter by filling out an online form by February 28, 2010. There are three prizes: a seven-night trip for two to Kiawah Island; a six-night trip to Key West; and a three-night trip to Nassau. All trips include air and hotel.

The second sweepstakes is from JetBlue. Follow the link to enter by January 31, 2010, for a chance to win trips for two to New York City, Las Vegas, Los Angeles, Orlando, or Aruba. Trips include hotel, air, and a rental car.

I’ve entered both sweepstakes, so sharing them with you is not the rational thing to do, since it decreases the odds of my winning.

Think of it as my Christmas present to you. It’s a present wrapped in a question mark, to be sure. But the price is right.

Did I mention free?