The Pursuit of Free Travel: Inside a Year-Long Quest to Win a Trip

Barbara Benham’s New Year’s resolution for 2006? Win a free trip. And why exactly does one resolve to do something that, ultimately, is out of one’s control? That’s one of the things I wondered when I came across Benham’s Travel Contests blog—Update: Sept. 26, 2006: It’s now the Travel Sweeps blog—which weaves sharp observations about travel and life—she’s a Washington D.C.-based writer—with details of the many travel sweepstakes and contests she enters. I contacted Benham via e-mail to find out more about her quest for free travel.

World Hum: On average, how many travel sweepstakes and contests are you entering?

I’d say I’m entering at least 20 a month. I don’t keep a log and I don’t blog about every contest I enter, so I’m not sure of the exact count. When I started, things were really hopping and it was more like one a day, seven days a week. It was right before St. Patrick’s Day, so there were several sweeps to Ireland. This universe is part thematic, part random. I could enter more, but I only enter sweeps I actually want to win, sweeps where if I did win, I could actually take the trip.

Going into this, I had no idea there were so many travel sweepstakes out there. I thought I’d enter one or two a week. I didn’t even know the difference between a contest and a sweepstakes. I was totally green.

And why, exactly, are you doing this?

On one level, my goal is totally practical. I want to win a trip. I’m doing my MFA right now, and the tuition costs have effectively wiped out my travel budget. I still cringe when I think of the trips I could have taken with that money. Add to the mix the yo-yo cash flow of freelancing in a one-income (mine) household. But it’s more than these temporary tuition-induced budget restraints.

I also wanted to play with the idea of making my luck good again. I’d had a few personal blows, a divorce, the deaths of several loved ones, including my father, as well as a smattering of professional disappointments. I just wasn’t feeling lucky. Not in a self-pitying way. I’m basically an optimist. And I’m well aware that my luck slump hasn’t been terrible in the grand scheme of things, I haven’t, touch wood, had any off-the-charts tragedies befall me. But objectively speaking, more bad things seemed to be happening than good things. I wanted to feel lucky again. I think as a culture we downplay the degree that luck plays in our lives. The collective assumption is one of can-do-ism, in fact, it’s more like anyone-can-do-ism, fueled by an over-reliance on the concept of self-determination. Sometimes I feel like telling Oprah and her ilk to go jump in a lake.

Then a friend won a trip to Hawaii, totally unexpectedly. She hadn’t even entered a contest, it had something to do with a public television fundraising solicitation. And that inspired me. I thought, I love to travel so much, and I’m in this funky position where travel is not in the cards for a stretch. Maybe I should challenge my preconceived notions about luck, and try, systematically, to win a trip. I made a New Year’s resolution to do that. Of course I forgot about it the next day. Then in early March, a line in an online column by Gore Vidal jumped out at me: “Life is mostly luck!” In addition to being stunned by his use of the exclamation point, it got me thinking about the whole luck thing again. And that reminded me of my New Year’s resolution. I started Googling that evening.

Any particular trip you want to win most?

One of the first sweeps I entered was for a 15-day trip to Australia with a wildlife scientist. It was sponsored by National Geographic, so you knew it would be top flight. You’d go to the Great Barrier Reef, the Outback, Tasmania. It just sounded sensational. I was pining for that trip for my son as much as for me. He’s nine and he’s been asking to go to Australia since he was four. I have no idea where that came from. Plus, he’s a nature nut, and this trip, had I won and had I been able to bring him along as my traveling companion, would have been a dream-come-true kind of trip.

Another one that sent me over the moon was an African package I found on Donald Trump’s travel Web site. I didn’t even know he had a travel Web site. I was Googling “Win a safari” or some such and discovered it that way. You’d fly into Johannesburg for a night, then fly to Botswana and stay a few days at three different camps and lodges, including The Chobe Safari Lodge. When a sweeps lists the accommodations, and many do, that takes the fantasy to a whole other level. Plus, it would have been a hoot to go to Africa for the first time on Donald Trump. It would have made a hell of a story. Not so much to publish, though that’s always a possibility, but more for the life narrative, a good-for-the-laugh story to tell family and friends.

Those two have come and gone. More recently I’ve been coveting a week at Rancho La Puerta in Tecate, Mexico. That will close by the end of July. I’ve been to Mexico. The draw with this one is invigoration and relaxation, plus history, since it’s one of the first destination spas. It was founded in something like 1940. Another sweeps that’s been given me a vicarious thrill recently is for a week at 9 Beaches, this casual resort in Bermuda. It’s got 80 or so cabins sprinkled around some serious beachfront acreage. Some of the cabins are on stilts in the water. That’s a monthly sweeps, if I’m not mistaken. So, it’s all over the map.

Have you had any epiphanies or gained any particular wisdom from your quest?

I suppose I’ve had a series of miniature epiphanies. This is a lot more fun than buying a Powerball ticket at the liquor store across the street every day. Not that I buy a Powerball ticket at the liquor store across the street every day. Entering these sweeps is a much more productive way for me to intertwine two of my biggest addictions, travel and the Internet, than just meandering online, clicking here and there and fantasizing about the next swell place to go.

I also love the blogging aspect of this. I’ve been looking for a vehicle around which to blog for a while. This approach, purposeful blogging, works better for me than just rambling on and on about my little life—though I indulge in plenty of that in my blog, mainly around trips taken and not taken and to be taken. As for the luck thing, I can’t decide if I’ve had a complete change of heart, if I’m beginning to think there is something to this self-determination business. All I know is I’m having a blast. I don’t even care if I win a trip. In fact, I don’t expect to win a trip. Of course, I would love to win a trip. Who wouldn’t want to win a trip? Now, did I make my luck? Maybe. Or maybe I just got lucky.

Indeed, Barbara. Who wouldn’t want to win a trip. Thanks and best of luck.

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