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jessie festa, solo female travel blogger

Welcome, traveler!

I’m Jessie, and I believe that life is a journey.

But our path isn’t always clear.

We’re influenced by so many outside voices — family, friends, the media, society — that we sometimes silence our own inner desires.

Booking that dream trip. Going on that yoga retreat. Starting a travel blog to become location independent. Setting off as a solo traveler for a summer abroad; these can all be put on the back burner, simmering slowly in our souls for another day.

(I know the reality of this, because I’ve been there myself, and you can read my full story below).

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Let me ask you something, though:

If you don’t set off on the path to making these big travel dreams happen now, then when?

Do you really want to be standing at the trailhead years from now wondering “What if?”.

What if you’d started that travel blog and became location independent?

What if you’d spent that summer abroad and gave yourself the opportunity to be transformed by travel?

What if you’d stopped letting excuses hold you back from creating the life you want?

Because you absolutely have the power to do so!

And, I'd love to help! 🙂

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Jessie on a Journey offers an honest look into the adventures, advice, and detours of your travel blogging BFF (me!).

Whether you’re a solo traveler craving spontaneity, a wanderer in search of more than your typical sightseeing, or a blogger with dreams of making travel a profitable lifestyle, this is the destination for you to bring more meaning and fulfillment to your journey.

Awaken your curiosity as I share real-talk and resources for exploring the world — and experiencing life — #BeyondTheGuidebook.

And for those wanting to learn how to become digital nomads themselves, you’ll find loads of free professional blogging resources as well as in-depth blog posts and episodes from The Profitable Travel Blogger Podcast.

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What I Do

How can I help you
travel toward your best life?


Unique Travel Experiences

I've got loads of free resources for travelers wanting to explore the world beyond cookie-cutter itineraries, from travel personality quizzes to trip planning printables & more!


New York City
Photo Journeys

Go on a New York adventure that’s part photo shoot, part walking tour that includes a custom itinerary and professional photos of the day for you to keep!


Confidently Travel The World Solo

You don't need a partner to explore the globe. Learn how to feel confident while mastering the art of traveling solo in this free e-mail course.


Profitable travel blogging

Along with my travel blogging courses and Travel Blog Prosperity membership, I offer a ton of free resources to help you grow your blog's traffic & income!

jessie festa, solo female travel blogger

My Story

The short version


Once upon a time there was a young woman who was told by society that in order to lead a fulfilling life she had to graduate college, get a 9-to-5 job and live a settled life with two weeks vacation per year (because obviously if you want anymore than that you’re just immature, selfish and lazy. Duh.) 

Despite resistance from loved ones, she decided to go the “immature” route, waving goodbye to her short stint in corporate America, and starting a business called Jessie on a Journey that allowed her to get paid to be creative, be her own boss and travel however much or little she pleased. She traded suits for suitcases, and her “office” is typically the nearest coffee shop or an airplane tray table. She lives happily ever after. The end. 

The Longer Version

Have you ever felt like the “right path” was the “wrong path” for you?

Yeah, I’ve been there.

Here’s the skinny: I was born and raised in New York — where I am also a certified sightseeing guide — and grew up traveling, mostly Caribbean cruises and North American road trips.

In 2010 I received my BA/MA in Communication & Rhetoric from the State University at Albany in New York, with the goal of getting into non-profit communications. By the time I graduated I had already had some inspiring travel experiences — studying in Australia, backpacking Europe solo, doing a homestay in Ghana, hiking my way through China and teaching English in Thailand.

You probably saw this coming, but I soon realized I wouldn’t be able to give up the complete freedom to travel. My travel experiences were what made me feel like I was truly living.

jessie festa, solo female travel blogger

When I finally got a “real job” they wouldn’t let me have any time off for travel until I had been there for six months. And even when I got the time off, it was only two weeks for the whole year.  I loved slow travel and really spending time in a place to get to know it, and knew in my heart the job situation was not going to work. I couldn’t stop thinking about how alive travel made me feel and how stagnant I felt working in an office. I was on someone else’s schedule following someone else’s rules; I wanted to live my best life and do things my way.

When I quit, my friends and family of course did not approve, but travel was something I felt really strongly about. I decided I didn’t care what they thought. If they loved me they would accept my choice. 

I didn’t want to be one of those people that did the same thing everyday and lived a similar life to everyone else. I wanted to live my life.

So I started waitressing full-time until I could come up with a plan, which allowed me to work overtime while I was home to pay off loans and bills, but also request off freely when the travel bug would hit.

Then one day I stumbled upon a travel writing class (funny enough, I teach a few myself now) and signed up. I loved writing and loved travel. Meeting the other students and alumni and reading blogs, I realized it was possible — as in real-life-this-isn’t-made-up — to combine my passions and make a living doing what I loved. 

Today I split my time at home in NYC and on the road. And even though I travel somewhere almost every month — mainly on my own — I still have a bucket list and things that make me nervous. But once you take one step in the direction of your dreams you’ll be able to take another.

Life is an adventure. I want to experience it to the fullest. And I want you to, too!

I see too many of my friends and family working jobs they’re unhappy in and living their lives in a way that doesn’t completely fulfill them. Even if you’re not in a position to take travel to the full-time level, it is still possible to enrich your life by exploring the world.

Check out the blog and find adventures you might be interested in having yourself and start planning the trip of a lifetime.

Happy trails!



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