Welcome, traveler!
I’m Jessie, and I believe that life is a journey best explored on your own terms.
I’m an NYC-based solo female traveler obsessed with active outdoor adventures, multi-day trekking, and immersive cultural experiences you won't find in standard guidebooks.
After studying abroad in Australia, I caught the travel bug but couldn't find anyone to go with.
Instead of waiting around for others to clear their schedules, I started exploring the world alone.
It was the best decision I ever made. ✈️
Not only did it give me complete control over my trips, but it helped shape me into the person I am today.
I want to help others enjoy the benefits of solo travel too.
My goal:
To empower you to confidently travel solo and create incredible memories around the world, whether it’s your first time setting off on your own or you’ve done it before and are looking for your next solo destination.
Quick Facts About Jessie on a Journey:
✍️ All of my content is 100% human written (no AI slop here!) and based on first-hand experience. Thank you for supporting an independent creator.
🏔️ Along with being an avid solo traveler I'm *obsessed* with trekking. Some of my favorite multi-day hikes have been the Peaks of the Balkans, Heights of Alay in Kyrgyzstan, and Mohare Danda in Nepal.
✨ While I also visit popular attractions, my favorite travel moments happen when I'm immersing myself in local culture and going beyond typical top 10 lists.
🗽 I'm a local New Yorker who regularly shares NYC travel tips. I also own NYC Photo Journeys, which offers photo tours, photoshoots, and custom travel planning.
❤️ 1% of NYC Photo Journeys profits get donated to charity. You can learn more about how my business gives back on my Sustainability & Social Impact page.
✈️ As travelers, I believe it is our responsibility to respect local cultures, minimize our environmental footprint, and prioritize sustainable tourism. Just because something is offered does not make it ethical — which is why it's important to do your research before booking.
💻 I also teach travel creators how to build full-time blogging businesses. If that is of interest, join my free 5-day Travel Blogging Course here.
Just a few of the MANY lessons you’ll learn from this travel blog:
🗽 64 Best Non-Touristy Things To Do In NYC (From A Local)
💻 How To Become A Digital Nomad With No Experience
✈️ 25 Important Tips For Flying Alone For The First Time
🔐 17 Safety Essentials You Can't Afford Not To Pack
🏔 How To Spend 2 Unforgettable Weeks In Morocco
🏝 15 Best Caribbean Islands For Solo Travel
🥾 Hiking The Stunning "Path Of The Gods" On Italy's Amalfi Coast
😂 16 Short, Funny Travel Stories That Will Make You Laugh Out Loud
What I Do
How can I help you
travel toward your best life?
Unique Travel Experiences
Snag free resources for travelers wanting to explore the world beyond the guidebook, like travel personality quizzes, trip planning printables, and more!
NYC
Photo Journeys
I offer NYC photo tours, private photoshoots, and custom trip planning, perfect for capturing memories while exploring the city!
Travel Solo Confidence
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 membership, I offer a ton of free resources to help you grow your blog's traffic & income!
My Story
The short version
Once upon a time, there was a young woman who was told the key to a fulfilling life was a 9-to-5 job, two weeks of vacation, and a steady climb up the corporate ladder.
She gave it a try — until a failed group trip to Europe turned into her first solo adventure.
That unexpected journey changed everything.
Hooked on the freedom of solo travel, she left corporate life behind and launched Jessie on a Journey, a blog that lets her travel the world, work from anywhere, and help others do the same.
She traded suits for suitcases, and now her “office” is wherever adventure calls.
The end. (Kind of.) 📖
The Longer Version
Have you ever felt like the “right path” was the “wrong path” for you?
Yeah, I’ve been there. 😅
I was born and raised in New York — where I am also a certified sightseeing guide — and grew up traveling, mostly Caribbean cruises and US road trips.
Travel was always present, but it wasn’t until college that it started to take hold of something deeper.
While earning my BA/MA in Communication & Rhetoric, I studied abroad in Australia — my first real taste of independence abroad. I was hooked.
Soon after, I planned a backpacking trip through Europe with friends. Until one by one, they dropped out.
I almost bailed too…but something told me to go anyway. It wasn’t just a trip. It was my first true solo adventure.
What started as a backup plan turned into a life-changing experience. The freedom, the confidence, the ability to follow my own curiosity — I didn’t want to give that up.
That solo leap opened the door to everything that followed: a homestay in Ghana, cycling through India, teaching English in Thailand, backpacking South America solo.
The more I traveled, the more I craved that feeling of being pushed just beyond what I thought I could handle — and growing because of it.
Still, I tried to follow the expected route. I got a “real job” for a bit, only to learn I wouldn’t be allowed any vacation time for six months, and even then, just two weeks a year.
The office felt more like confinement than stability. I was stuck under fluorescent lights, living on someone else’s schedule, following someone else’s rules.
So I left. Not without fear. And definitely not with everyone’s approval. But I knew I couldn’t spend my life living by someone else’s definition of success.
I waitressed full-time while figuring out my next move — a job that let me pay the bills and travel when the bug hit.
Then one day, I stumbled upon a travel writing course (funny enough, I now teach a few of my own).
That course changed everything. It showed me I could combine my love for travel and storytelling and turn it into a career.
That’s how Jessie on a Journey was born — a solo female travel blog rooted in active adventure, cultural immersion, responsible tourism, and helping others go beyond the guidebook.
Today, I split my time between NYC and the road.
I still travel solo more often than not.
I still get nervous before big trips.
And I still believe that the best journeys are the ones that push you just a little past your comfort zone.
Travel — even in small doses — has the power to shift your perspective, grow your confidence, and help you build a life that’s fully your own. I created this blog to help you experience that.
Whether you're dreaming of your first solo trip, planning an offbeat escape, or just searching for something more meaningful, you're in the right place.
Let’s rewrite the map together. 🗺✈️
THE NEW STRATEGY FOR PROFITABLE TRAVEL BLOGGING
Short on time but eager to learn how to REALLY grow your blogging business? This FREE 5-day email course was made for you.
