For Over A Decade Jessie Has Been Blogging About Her Travels While Also Starting Several New Businesses Along The Way
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GAFFL connects solo travelers with similar itineraries to explore destinations together. Whether you are backpacking in Asia, road tripping in Australia, or exploring national parks in the US, simply type the destination you are traveling to, find travelers who are going there at the same time as you, connect with them, plan trips, meet, and travel together.

GAFFL
27th Jan | 7 min read

Table of Contents

    At GAFFL, we love to publish inspiring travel stories from adventurers around the world. You can connect with adventurers from 170+ countries on GAFFL, meet up, and explore destinations together. In this post, we are featuring Jessie, an adventurous solo female traveler behind the blog Jessie on a Journey

    She’s also the founder of Epicure & Culture, a sustainable tourism magazine; NYC Photo Journeys, a photo experience company; and Travel Blog Prosperity, a community for travel creators wanting to turn their blogs into profitable businesses.

    Jessie’s other passions include yoga, hiking, 360 videography, playing with my cats, and seeking out the best spicy cocktails in a city.


    Tired of traveling alone? Connect with users from over 170 countries to plan trips and travel together!
    Try GAFFL

    Why I Started Traveling

    Growing up I traveled with my family, mainly Caribbean cruises and US road trips to amusement parks. I always loved these trips — though it was really studying abroad in Sydney that made me fall in love with travel. 


    Everything felt new and exciting, and I loved how my curiosity was awoken. I felt like the best version of myself; open to new things, outgoing, and excited for growth.

    The problem I encountered back home was having to wait for others to also be ready to travel. That’s why I now travel solo 90% of the time — and I love it! 

    I Try To Travel As Much As Possible

    Before the pandemic, I traveled about once per month. Now I’m just starting to get back into it. The issue is I run a photo tour company in NYC and if I got stuck abroad it would be a big issue with cancellations. But I am excited to get back out there!


    A few things I love to do when traveling include hiking, eating in local homes, booking at least one walking tour (preferably a food tour!), and trying to find unique local experiences you don’t typically read about in guidebooks — like creating my own fresco art in Florence and scooter snorkeling in Antigua!

    How I Choose Where To Travel Next

    Typically I go to places that I’m invited to as a blogger or that I find flight deals for. To find these, I set alerts on my phone to be notified when my favorite Twitter accounts for flight deals tweet.

    In terms of time, I spend in a particular destination, it totally varies! I just went to Punta Cana for four days, then before the pandemic, I went to Nepal for two weeks. The last time I went to India I spent about three weeks traveling Northern India -- plus some time on the country’s southwest coast in Goa to relax on the beach.


    In terms of preparation, one of the most important steps I take is researching any visa or entry requirements. This is particularly important now with the pandemic, as every country has its own rules. It would be very upsetting and stressful to arrive somewhere and be told you can’t enter the country simply because you’re missing a document!

    How I Pack For My Trips

    I’m a carry-on-only traveler, so if it doesn’t fit in my carry-on suitcase and backpack it isn’t coming! A few must-haves include my DSLR camera, pickpocket-proof clothing (particularly when I’m traveling alone), earplugs, and an eye mask (because you never quite know if your hotel or Airbnb will be noisy), and Emergen-C packets (since travel can increase our chances of getting sick).


    More recently, I’ve started bringing my 360 camera everywhere I go -- especially when traveling! You can make really fun immersive content, like this video of me walking Bavaro Beach in the Dominican Republic.

    One Of My Best Memories Meeting Someone New While Traveling

    I have so many! One of my favorite stories is when I was traveling solo in Mendoza, Argentina on my 25th birthday. I didn’t want to celebrate alone, so I posted a message on CouchSurfing asking if anyone would like to come out with me.

    I ended up having 11 people take me out for dinner and dancing! 


    Within five minutes of meeting I truly felt like I’d known these people all of my life. They were so welcoming and warm to be around. It ended up being one of the best birthdays of my life!

    How I Started Blogging

    One misconception is that solo travel means you’re alone all of the time, but in reality one of the biggest joys of traveling solo is having ultimate freedom over your itinerary while also getting to spend time with others you meet along your journey. 

    My love of solo travel is actually what inspired me to start my blog. At the time, there weren’t many resources for solo female travelers out there, so I set out to create one and help women through the free blog, social, email, and video content.

    I started Jessie on a Journey, in 2011. At this time, I wasn’t really sure what “blogging” was, but I was obsessed with travel and determined to find a job where I could be my own boss and travel the world. 


    So I started my site, pursued blogging aggressively, and was able to take it full-time within a year.

    For anyone else wanting to take this route, I would highly recommend getting clear on what you want to cover and who would benefit from this content. It’ll make creating content and products that resonate with people so much easier. 

    Moreover, having a well-defined niche (ie “budget family travel” vs “travel”) makes it easier to rank your content in organic search, as Google knows what your expertise is.

    And for those looking for additional resources, I have blogging courses, my Profitable Travel Blogger Podcast, and free blogging resources too!

    How I Manage My Travel Costs

    I consider myself a value-focused traveler; as in, I splurge when it is worth it to me and cut costs where it makes sense. 

    For instance, when traveling solo I don’t feel the need to eat in nice restaurants, so food is an easy saving for me. 

    However, I love interesting experiences and tours -- which are also great for meeting people -- so I tend to spend more money on those.

    Countries I’ve Traveled To So Far

    Funny enough, I actually don’t count countries, though I can say I’ve been to every continent aside from Antarctica. 

    One destination I’m hoping to go to soon is Tanzania, as my honeymoon was supposed to be there; however, due to the pandemic, it got changed to a two-week California road trip, which was also awesome!


    In terms of epic trips, cycling through Kerala in India was amazing. It was just myself and a local guide and we cycled for two weeks through cities and countryside, hiked through national parks, stayed at eco-campsites, and enjoyed the natural beauty of the state.

    A few other unforgettable trips have been hiking in the Himalayas in Nepal (the Mohare Danda trek is amazing!), visiting Bhutan solo, and staying with an herbalist family in Slovenia for a homestay.

    How I Manage Work And Travel

    I’m based in NYC, so I typically try not to work much when I’m traveling aside from taking notes and saving photos and videos to the cloud. 


    If I need to work, I set strict timeframes so that I’m not spending an entire day at my laptop. That is definitely not how I want to spend my time on the road!

    My Advice To New Bloggers

    If you plan to blog or work from the road, realize that moving all of the time makes it tough to get work done and grow your business. If possible, choose a home base -- even if you move every few months -- and try to create some semblance of a schedule. 

    What I Wish I Had Known When I First Started Traveling

    I wish I would have been more aware of sustainable tourism issues that exist in the world. When I was younger, I assumed that if an activity was offered by an operator it must be ethical, because otherwise how could it even get to market?


    After years on the road, I’ve learned that this sadly isn’t the case. You have to do your own research. For instance, here are a few irresponsible tourism experiences to be aware of.

    In short, make sure your trips positively benefit the places you visit. Travel isn’t a right, so make sure you respect the privilege to see the world.

    Tired of traveling alone? Connect with users from over 170 countries to plan trips and travel together!
    Try GAFFL

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