Living The Dream: Enjoy The Simplicity Of Places

Living The Dream

Who's this?

We met Anna in Puerto Rico and she really is legendary. She took us on some crazy adventures looking for secret beaches and million dollar mansions in the rainforest. Come see how Anna is Living The Dream.


What is the first country you visited? Who with and why did you choose it?

I went to Prince Edward Island in Canada with my family for a ten day camping vacation. The campground was on this enormous, beautiful, red sand beach. I have great childhood memories there.

When did you start a travel lifestyle? What inspired that change?

I began traveling about three years ago. My mother had traveled extensively in her twenties, she had been a nanny in Norway in the winter and backpacked Europe in the summer. Both of my parents had always encouraged me to travel. When I got out of a long term relationship, I decided it was the perfect time to chase after my dreams, literally. So I quit my job, sold my car and backpacked Europe for four months. It was the first time in my life I was free of being on a lease, or in a relationship and there were no job obligations. It was the ultimate feeling of freedom that most people never get the chance to experience. I was hooked. I had enjoyed those few, short months so much that I haven’t stopped traveling since.


Do you have a base you travel from? Or is it continuous travel? And why do you choose that style?

I currently do not have one home base, but several. I feel at home in Los Angeles, New York City, Florida and a couple of other places I frequent. I choose this style over the option of having a set place to come back to because I have incredible friends in each place and I could never choose to just be in one place. It also helps that those places have some of my favorite parks, beaches and things to do. Being in those areas always keeps me recharged and inspired.

How do you fund your travel lifestyle? Is it something you do when travelling or are you a saver?

Saving money is not my strong point. After my first big solo trip backpacking Europe I felt I had found my place in the world in traveling so I had to make some changes in how I handled money. I bent my life around it to make traveling a long term sustainable option. I was willing to do what it took to keep it going so I started by taking whatever temp work I could find. Now, I do social media consulting remotely, photography and I’m a travel nanny one month out of the year. I do not have any debt and I have learned to live very cheaply. Thankfully, because the benefits of getting to travel for me outweigh spending my money on rent, car payments and other bills I would otherwise have.

If you could tell yourself one tip before you started your travel lifestyle, what would it be?

I would tell myself to make sure to take time for myself and have a few down days to relax. Every day doesn't have to be an adventure. I’d want to remind myself to enjoy the experiences in the simplicity of some places.


What does 'Living The Dream' mean to you?

I used to think living the dream meant having a nice house, car and all of that. Several years ago I redefined society's definition of success for myself. Now ‘living the dream’ simply means to me that I am happy. And as far as I’m concerned I’ve achieved that because traveling brings me more joy than anything else I’ve done in life.

You can find Anna here - 

Website: The Legendary Adventures of Anna

Facebook: The Legendary Adventures of Anna

Twitter: @crazyintherain

Exploring the world for some ridiculously crazy adventures.

Reader Comments...

"I respond to every comment by direct private email. I look forward to your feedback" -

I have been seeing Anna's photos float across my FB feed for awhile. It's nice to learn more about her. Lovely interview!

Alysia Sep 15th, 2013

Nice one Anna, you are an inspiration for many others. There are so many people out there that would love to travel but are scared of doing it because they don't know how doable it can be. Keep going and happy travels! :)

Franca Calabretta Sep 15th, 2013

Happy travels Anna!! I have been following your Facebook page for quite some time now. You're an inspiration to us all! :)

Desiree Sep 15th, 2013


Ryan Royce Sep 15th, 2013

I first met Anna when she Couchsurfed at my place in L.A and I found myself immediately inspired by her free-spirited nomadic lifestyle. Her attitude has always been "Do what makes you smile", and I think it's a great way to live. I hope you know how much of an inspiration you were for me, Anna.

Miles Sep 15th, 2013

Great post and amazing photos, especially the first one with the rock in Norway.

meital seekatrip Sep 15th, 2013

Thanks for sharing your travel experience, Anna! I enjoy all the photos you share & I like how you are taking life so simple. You are really an inspiration. Best wishes always.

Jubran Sep 15th, 2013

Love your adventurous spirit. Like reading your blogs and posts. You are living your dream life. Got to admit you are a brave courageous girl flowering into an amazing woman.

Murali Vogety Sep 15th, 2013

Great interview. I love seeing Anna's pictures and inspiration quotes pop up on my newsfeed. Congrats on redefining your dream life, something many don't and will never have the courage to do!

Phoebe (Short Road to Happy) Sep 20th, 2013

Your happiness and joy for life shine through your smile in your photos. It makes me happy to think that people are not shackled to concept of success with houses, salaries and 80hr weeks. Inspirational stuff Anna and keep living the dream. Have a wonderful day.


Julian John Sep 21st, 2013

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