The Art of Unplanned Travel: On the Road with Carole Rosenblat

This is a traveler case study. (Read others or nominate yourself.)

A quester and traveler, Carole Rosenblat decided to take a deep dive into rarely explored territory: the art of unplanned travel. She runs a blog and lets her readers choose where she travels, giving herself only a few days to get from one place to another.

Introduce yourself.  

I’m Carole. I was born in Oak Park, Michigan, just outside of Detroit (you’ve probably heard of 8 Mile thanks to Eminem – I’m from 9 Mile).

For seven years, I worked in a bank before I walked in one day and said, “I quit! I’m going to sail the Caribbean.” Three weeks later, I was working on a ship built in the 1930’s, and very seasick for awhile. Since then, I’ve worked on cruise ships, been a camping/adventure guide, and worked as an international tour manager.

Now, I’m traveling the world, with a twist: I let readers of my site, Drop Me Anywhere, vote on where I travel.

I write as I travel so readers – who I call my Virtual Travel Buddies – get to be on the road with me. I include readers in on my quirky observations and my challenges and mistakes along the way (I get lost a lot). While traveling, I find organizations or projects with which to volunteer and I profile them on my philanthropic site, Rebel With a Cause, to give them exposure to a wider audience.


What inspired you to travel in such a unique way?

I love to travel, but hate planning it. I realized sometimes I wasn’t traveling strictly because I was overwhelmed with organizing it.

Then, while participating in a Twitter chat about travel, this question came up: “If you had a travel show, what would it be called?” The answer fell out of my fingertips: Drop Me Anywhere!

The supportive response was overwhelming. Still, I resisted. But it stayed in the back of my head. Finally, I wrote a well-known travel writer I’d helped with a story and asked, “Is this something?” He loved the idea and told me he wished he could do it. That was a real boost and suddenly I was making plans – well, plans for unplanned travel.

Did anything else push you out the door?

I had a health scare. Coupled with a friend passing away from cancer and knowing my mom was only seven years older than I was when she passed away – well, I was feeling my own mortality.

Call it a midlife crisis, or just wanting to live life out loud, but now was the time.


Can you tell us about a memorable encounter?

My Virtual Travel Buddies had voted I go to Mexico and visit the ancient Mayan ruins. To volunteer, I found a library in Akumal, a poorer area, and the Hekab be Biblioteca is an amazing place that provides kids with an after school program with a variety of activities and helps them find a love for reading (and learning English).

Upon arriving in Mexico, I drove directly to the library and started meeting the kids. I noticed a little girl who was sitting by herself, drawing. I sat down with her and began drawing and asking her questions in my basic Spanish. She refused to answer and pretty much ignored me.

A little boy came up to me, and in a combination of Spanish and body language he told me that this little girl could neither hear nor speak. That explained it.

I caught the girl’s eye and we began interacting. Soon she was pulling books off the shelves and telling me to draw some of the characters. My drawing ability is worse than my Spanish, but she loved it. At the library, she’s known as “Little Michelangelo” because of her love of drawing and painting.

I was only volunteering for five days, and in that time the girl, Estefani, along with the other kids, stole my heart. I was told that she and I bonded because I gave her unconditional love. I also think part of it was that neither of us spoke the language of the other children. It was so difficult saying goodbye. I will return here at some point to see “my kids.”

How do you pay for your travels?

I’ve rented out my home, sold my car (and most of my other possessions), which gave me a nice financial step forward. Plus, I make money writing for corporate clients and public speaking.

I get inventive with housing, too. I’ve signed up with a couple of house/pet sitting sites online so in some locations, I’m able to stay for free and even get a furry buddy for a bit. I also try to book overnight trains and get a couchette as it saves on a night in a hotel. I even stayed at a nudist RV resort!

I use as they give one free night for every 10 stays.


Tell us how you’ve overcome a low point.

Getting out of my house and actually doing this wound up being pretty scary. The idea had been fun and adventurous, until go time. Funny enough, I was reading The Happiness of Pursuit by Chris. During moments of sheer panic, hearing the stories of people who had overcome fears was supremely helpful. I felt like I were joining a club: The Fraternity of Questers.

Part of the fear was letting go of all my stuff. The house, the furniture. I didn’t realize how emotionally connected I was with my things. Then my friend April provided two great thoughts that I took with me: “You can never out-give God,” and “You can always buy new shit.”

What has surprised you while traveling?

I had no idea how lonely traveling can be. Most of my travels before this were solo, and I lived alone in Arizona and enjoy my own company. But going places where English isn’t spoken much gets isolating.

How have you combated that loneliness?

India has been the toughest place in terms of loneliness by far. On one of my worst days, I ended up in a small, hotel at Rathembore National Park, having beers on my patio with a retired German air traffic controller. Those moments of bonding with fellow travelers can help.

One way I combat loneliness is to go to the movies. Every country has different customs in theaters—like assigned seating and snacks that are not like anything we eat in America. And when the lights go out and the previews come on, I could be anywhere. Even home.

Anytime I can find a lavender scented candle, that helps too. The smell takes me right back to my house and the feeling is comforting.


The great debate: aisle or window?

Window – I like to “nest.”

Best travel tip. Go:

Don’t let the naysayers drag you down.

Usually, they’re just projecting their fears onto you. Don’t wait for anyone’s approval but your own.

Where are you headed next?

We’ll find out – I’m waiting for the votes to come in!

Follow Carole and chime in on where she travels on her site, Drop Me Anywhere, or via Twitter @DropMeAnywhere


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