Winning DoubleTree Travel Contest Makes Writer’s Dreams Come True

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London's Tower Bridge
Author Jenn Winter in Front of Tower Bridge when she was an intern in London.

Wanted: Six DTourists to visit North America, South America, Europe, Africa, Asia and Australia to create video, photo and written content about their visit. All travel expenses paid and generous compensation for work. To apply post a video of a must-see destination to the DTour website.

Seriously? How could I NOT apply for this amazing opportunity offered by DoubleTree by Hilton Hotels?

I’ve wanted to be a travel writer when I “grow up” for the past decade and this would not only be an unforgettable experience but a huge boost in my professional aspirations. Forget the fact that I only found out about the job mere hours before the application deadline, there was absolutely no way I could let this pass me by.

Backpacking in Chile
Author Jenn Winter backpacking in Torres del Paine in Chilean Patagonia.

Last Minute Contest Entry

I’m not exaggerating when I tell you that I sat on the floor in the hallway of the Canadian Backpackers Inn in Toronto, towel over my head, and recorded my voiceover about 10 minutes before the contest closed.

I’m sure that I raised more than a couple of eyebrows talking to myself under there, but I managed to upload my entry by 11:58pm. Whew! I then went back into the room I was sharing with seven snoring strangers and thought about how lovely it would be to stay in a nice hotel on my next trip.

On the Way to Europe

Fast forward a few months and I’m about to do just that! The powers that be at DoubleTree liked my submission enough to give me one of the six available DTourist positions. As a girl who has entered several travel competitions and never heard back, this is the equivalent of getting cut from the T-ball team one day and receiving an invitation to play in the Majors the next.

In many ways I feel like I’ve been working toward this moment for several years and I’m thrilled that my so-called big break was brought about in such an unbelievable way.

Pyramids of Giza
Author Jenn Winter at the pyramids of Giza.

As DoubleTree’s European DTourist, I am visiting Spain, Turkey, The Netherlands, Ireland and England. My itinerary is a great mix of places I’ve been before (Dublin and London,) new areas of countries I’ve visited (Costa Brava region in Spain) and places that I’ve wanted to visit (Cappadocia, Istanbul, Amsterdam and Chester.)

Hosted by DoubleTree

Though I haven’t arrived yet, each property has been simply amazing thus far – sending me congratulatory and welcome messages on Twitter and Facebook, compiling a selection of activities and experiences for me to participate in while I’m in town and offering to help me in anyway they can. The DoubleTree theme of CARE (Create A Rewarding Experience) is certainly alive and well.

I’ve been to Europe a couple of times but never in this way. My experience with that continent is similar to a lot of college educated Americans: I studied for a semester in Rome in 2003 and toted a backpack from hostel to hostel, slept on overnight buses and trains – even once in a train terminal in Bologna.

The following summer I landed an internship in London and was happy to let that amazing city suck my wallet dry as I earned college credit and rode the tube like a local.

Traveling Like a Grown Up

While those were unforgettable experiences I’m ready to “grow up” a bit in the way in which I travel. I bought myself fancy new luggage as a 30th birthday gift – to me from me – and am happy to give my big blue backpack a break for this adventure.

Despite having three decades behind me, I still refer to my future as “when I grow up,” and I think that this trip will mark a forward step in maturity for me both as a traveler and as an aspiring travel writer and photographer.

I’ve received fantastic feedback from fellow bloggers, friends and Twitter and Facebook followers. In addition, I’ve enjoyed researching the destinations I’m visiting by reading tips and suggestions from other bloggers – like Heather’s suggestions for Istanbul and Mary’s packing list for Amsterdam.

I am the first of the six DTourists to set out on my adventure, which is both exciting and a little nerve wrecking – I have no one’s mistakes from which to learn.

But as an oldest child, I’m used to trailblazing and, as my four siblings may or may not agree, setting the bar pretty high for the rest. I promise to provide quality content while on my adventure so please, follow along on my blog at

While she may call Chicago home, writer/photographer Jenn Winter is happiest when living out of her suitcase. Young, unattached and (not so) patiently awaiting her next adventure, she and her dog, Essie, run J. Winter Photography. Follow her on Twitter: @ALadyAway

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