The Time I Took a Walk in Cuba and Won $25,000

Havana, Cuba

My story starts in Cuba.

I was in Havana for a week on a US-approved cultural trip through Santa Fe Photo Workshops. Each morning at 6am there was an optional photo walk around a different section of the city. The first morning I went and didn’t capture anything that I liked. The second morning my alarm went off at 5:45 (2:45am California time) and I came thisclose to staying in bed. But it had rained the night before, meaning that there would potentially be good reflections, and I had wanted to go to Cuba for years so it seemed like a waste to sacrifice a morning walk to sleep. I got out of bed, headed downstairs, and met the few others who had also managed to escape the warmth of their beds.

We waited a little bit longer to see if anyone else was joining us and left the Hotel Parque Central around 6:15. We crossed the street and were walking along the park when an old American car pulled up to the curb in front of us. The car was lit from inside with a red bulb, and the lights around the park were glowing. It was a great scene. Not even checking the settings of my camera, I dropped down on a knee and took ten quick shots of the rear door opening, Man 1 (as I refer to him) getting out, Man 1 holding the door for Man 2 to get out and Man 2 leaving the car. We then continued with the hour-long walk.

Over the course of the week I put together a portfolio of my ten favorite shots, and one from that early morning walk made the cut – the seventh frame of the car sequence. I liked that particular shot because of the curiosity and anticipation. You can’t yet see who is leaving the car.

Conde Nast Traveler

When I got home from the trip, on my desk waiting for me was the newest issue of Conde Nast Traveler. I started flipping through it and saw their annual photograph competition. I had entered a few contests before, and had two of the top 25 finalists in a contest from National Geographic Travel a few years back which I thought was pretty cool, but in general I stayed away from photo contests since they never seemed that attractive. Sign away the rights to your work to maybe win a $100 gift card? No thanks. But I had subscribed to the magazine for over 20 years and really liked its writers and its style, and the prize – a $25,000 Dream Trip to anywhere – was better than I had seen in any other contests. Their contest rules were extremely reasonable as well – the magazine could utilize your photo as much as it wanted in print or elsewhere, but you retain full rights. I figured what the heck. I looked through my Cuba photos, chose the one of the man and the car from the morning walk and, a few clicks later, entered it into the contest.

Part of the contest involved internet voting – basically people clicking through the entries and liking the photos that caught their eyes. The voting didn’t count for much in the final judging criteria, but I still went onto Facebook and asked my friends to click through and like my photo. I wanted to get enough votes to at least get the attention of the judges. I got maybe 50 votes? The top photos had over 1,200 votes. But it was enough to get my photo noticed and selected as one of the 25 finalists.

The Essay

I was happy just being a finalist! They even printed my photo in the magazine with a couple of photos from other finalists, which was very cool to see. I also won a Clarisonic Skin Cleansing Kit, which two years later I still haven’t taken out of the box. Being a finalist though meant that the photo that you submitted no longer meant anything. Now there was an essay portion that would determine the winner: Tell us where you would go if you won the $25,000 Dream Trip.

Hmmm. I had always kind of traveled where I had wanted. And the places that were on the top of my travel list – Turkey and Antarctica – weren’t necessarily unique enough to win me a Dream Trip contest, nor did I have a compelling reason for wanting to go to either place. Then it occurred to me… I shouldn’t think of the contest as: where would I travel with $25,000? Instead, I should think of it as: where would I travel if I won $25,000 and if I had the magazine’s expertise in planning a trip? In other words, what could they do for me that I couldn’t do myself? The answer was Florence.

I had spent a year in Florence in college. I had been back several times solo or with friends. But I had never taken my kids there because I didn’t know what to do with them. I couldn’t picture any playgrounds. I didn’t know of any fun family activities. And I just couldn’t see my kids, at 2, 4 and 6, being interested in the art and history. So my essay was about how I needed the magazine’s help in planning a kid-friendly trip to my favorite city.

“Hi, is this Eric?”

It worked! They called me a few months later and told me that I had won. The magazine announced the win on Facebook and their website and I was immediately put in touch with their Director of Consumer News and Digital Community, Wendy Perrin, to plan the dream trip. Working with Wendy was a pleasure. My guidance to her was that everything should be as kid-friendly as possible, and we were up for anything that didn’t involve cycling or other activities that a 3-year-old couldn’t really participate in. She brought in Maria at Concierge in Umbria, one of her trusted travel experts, to arrange the details.

Florence

Eleven months later (due to the school calendar), we were off! We headed to London first for five days before flying to Florence for two weeks. It was a perfect trip, and I don’t use the term “perfect” lightly. Wendy and Maria, and Maria’s local guide Elvira Politi, set up an amazing itinerary for us that I never would/could have booked for ourselves. Beyond the prize money (which yes, we used every penny of), Maria, Wendy and Elvira’s expertise was invaluable. They booked cooking classes (pasta, pizza, chocolate, gelato), craft workshops (frescos, Florentine paper), arranged private guided museum visits and basically organized a true dream trip. Details from the trip are on my blog here. I went from being hesitant to take my kids to Florence to wanting to take them there every year…which is exactly what we’re doing, although on a much reduced scale. We went back last summer for a week, going to a few new places with Elvira, and we’re booked for another week next summer to do the same. Florence has become our kids’ favorite city and we’ve almost become locals at several of our favorite places, which is a really nice thing to be. And the trip permanently changed our travel habits. Instead of exploring independently, we are now much more apt to hire guides or book private tours. It adds a much deeper level to the experience and is well worth the money – even when it’s our money and not the magazine’s!

What I Learned

Advice that I would give to others based on this very cool experience:

1. Don’t sleep in! You can always sleep on the plane flight home. If you’re somewhere special, take advantage of it and see as much as you can – even if it means waking up early.
2. Enter contests! Someone has to win. But review the rules first and make sure that you’re not agreeing to egregious terms. Unfortunately Conde Nast Traveler doesn’t seem to be running the Dream Trip contest any longer – the link on their website doesn’t go anywhere.
3. Use travel advisers (Wendy Perrin’s Wow List is an excellent resource) or search on TripAdvisor for guides and tours wherever you’re going.

Epilogue

I just re-read this post, eight years after I wrote it and ten years after I received the call telling me that I had won. Back then the best part of this was having an amazing trip to Florence. But winning the contest literally changed my life. Having met Wendy Perrin and other Conde Nast Traveler writers who had inspired my travels, when I quit my job in healthcare a year later, I started writing about my own travels. I started this website, I started posting to social media, and I now make a living traveling with my kids and writing about it. It’s crazy to think back on that morning in Havana now – if I hadn’t gotten out of bed, I wouldn’t be a travel writer. And full-circle, Conde Nast Traveler has now hired me for a couple of assignments. They sent me to New Orleans to profile a hotel for their Hot List. And I worked with them last year on a perfect three-day Colorado itinerary. In neither case were they aware that I was only a travel writer because of them!

Your Turn

If you had won the Conde Nast contest, where would you have gone? And was there one single event, one moment, that literally changed your life? Please comment below!