Celebrity Travel Addicts: Jessica Festa of Jessie on a Journey

In this edition of Celebrity Travel Addicts, we speak with Jessica Festa, the renowned travel blogger behind Jessie on a Journey. We speak with her about how her love for travel was first sparked, the helpful travel blogging courses she offers to her readers, her favorite destinations around the world, and much more! Find out what to do in her native New York City when you visit and see where she’s headed next!

How did your passion for travel get started?

Luckily my parents had an interest in travel, though growing up it was a lot of Caribbean cruises and USA road trips to different theme parks. It was when I studied abroad in Sydney, Australia that I was really “bitten by the travel bug”. That was when I decided I wanted — more like needed — to make travel a major part of my life.

How many days/weeks are you traveling in any given year? What are the types of places you like to visit?

In my early and mid 20s I did a lot of three-to-four month backpacking trips through South America, South East Asia/China, and Europe. Now in my early 30s — engaged and living with my fiancé and cat — I typically do one week of travel each month, though sometimes I’ll go away for two-to-four weeks.

I just got back from one month in Nepal, and I’ll be heading to the Galapagos for a week soon.

I still love long trips from time-to-time, but I miss my fiancé and furbaby too much to leave for long stretches all the time like I used to.

You were born and raised in New York. What makes New York such a great tourist destination? What do you suggest people do when they visit?

What I find many people don’t realize is that New York — as a state — is huge. Of course there’s NYC, which is so culturally diverse you could “travel the world” without leaving the city. I actually lead photo tours here, and my guests always comment how incredibly it is that they’ll hear five or more languages being spoken on the Brooklyn Bridge alone!

There is also more nature than people expect. I actually saw dolphins jumping out of the water at Jacob Riis Beach in Queens last week! In Pelham Bay Park in The Bronx there are multiple waterfall hikes, and you can book a whale watching tour from Queens.

But New York also has incredible day and weekend getaways from the city. I mean, right on Long Island — that fish-shaped island jutting out of Manhattan on which Brooklyn and Queens are actually located — has seal hiking, shipwreck diving, and over 50 wineries along the North and South Forks, just to name a few experiences.

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About a five-hour drive from Manhattan is the 1000 Islands, a summer destination featuring 1,864 islands across New York and Canada.

In the Adirondacks, you can hike up mountains reaching 5,344 feet (Mount Marcy).

This is just a small sampling of all the things that make New York so great!

You started your travel website, Jessie on a Journey, back in 2011. What was the inspiration behind it? What makes it different from the other travel content out there?

As I became more and more obsessed with travel during college I started to have a major change of heart about what I wanted to do in life. I went from wanting a swanky Manhattan PR job to just wanting to figure out how I could continue traveling.

I graduated with my BA/MA in 2010. At this point I didn’t really know what a blog was beyond a sort of online journal. But as I was searching for travel jobs, I saw there were normal people — as in, non-celebrities — earning an income through travel blogging. And so, I pursued it aggressively and was able to quit my waitressing job within a year.

In terms of what makes mine different from other travel blogs — particularly other solo female travel blogs — there are a few things:

*My style is conversational and in-depth. Before writing I will think of every question my audience may have and will try to answer it. I’ll also include lots of photos and videos — and often assets like infographics, packing lists and travel planning printables to make sure everyone can truly replicate my trip.

*My tagline is “taking you beyond the guidebook,” and I always aim to weave offbeat and lesser-known experiences with sustainable tourism.

*I also cover travel blogging as a core topic for those wanting to really make this an ongoing lifestyle.

In addition to sharing helpful travel tips on your site, you also offer custom trip planning and several courses. What can travelers and bloggers expect when they work with you and learn from you?

My main products are my NYC photo tours and my online blogging travel courses, with my signature offering being my Travel Blog Prosperity membership community.

In terms of working with me as a blogger trying to build a business, students can expect:

*My teachings are mission-oriented. Whether you’re taking my course on working with brands, my Facebook Ads masterclass or something else, I tie all strategies into the overarching idea of creating a mission-based website aimed at helping a specific group of people do a specific thing. Basically, I believe focusing on growing and nurturing a community is both ethical and can help make your business sustainable.

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*I don’t hold back. I’ve heard over and over again that one problem people see in other online courses is they learn an idea but not how to apply it in real life. When I create my courses my goal is to never leave anyone at the lesson, and to provide all the necessary assets and examples for implementation.

*I teach in a step-by-step manner. My courses are all about clarity and helping students hit milestones — in the right order.

*I’m a mentor and friend. My blogging business is very human. I personally respond to all student emails, and have grown friendships with many of my students, particularly my Travel Blog Prosperity members as we have three live calls each month.

What do you want audiences to gain and learn from your work?

In terms of what I want people to gain and learn from my work, my blog really has two parts:

*Helping traveler bloggers build profitable online businesses

*Helping to empower people — mainly women — to travel solo and stop waiting

While these different missions exist, they both fall under the umbrella of helping travelers to feel confident creating their dream lifestyle, even if it goes against societal norms or what they’ve been brought up to think they should do.

What are the top three destinations you’ve visited?

It’s always hard to narrow down favorite destinations. There are so many incredible options! But three I absolutely loved:

a) Panama. I’m partial to Central and South America as you can see some of the most incredible landscapes, embark on truly unique hikes, stay in rural villages to have experiences you may not be able to have at home. While there are many destinations in Latin America I love — I was really torn between putting Panama and Patagonia — I just really loved the two weeks I spent in Panama. More on that in the next question!

b) Bhutan. The culture here is incredibly well-preserved, and you can do everything from hike up to the ancient Tiger’s Nest Temple, trekking in Jakar, The Switzerland Of Bhutan to seeing the rare Black-necked crane in the Phobjikha Valley. Yes, the daily fee to visit Bhutan makes it pricey, but it’s well worth it to explore the beauty of this country without the crowds.

c) Nepal. This was my most recent trip. Wow! Hiking through the Annapurna Himalayas was a dream experience for me, and I got to do a lesser-traversed trail called the Mohare Danda Eco-Trail. It was an incredible opportunity to connect with locals, see animals like yaks and water buffalo, and see some of the world’s highest peaks.

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Give us your ‘Top 5’ list for one of your top 3 destinations. Like a mini-guide or a to-do list of sorts. It can be anything from your favorite hotel, the best place to have lunch, the best sightseeing, etc.

Here is a mini guide for Panama:

In Panama City, sip a cocktail at 66 storeys at the Panaviera Pool Bar.

From Bocas Town, take a short boat ride to Bibi’s on the Beach for a sunset seafood meal on the water.

In Bocas del Toro, stay at the La Loma Jungle Lodge & Chocolate Farm.

In Boquete, experience some of the best hiking Panama via cloud forest trails like the Pipeline Trail and the Lost Waterfalls Trail.

In El Valle de Anton, do the La India Dormida hike. There are amazing views and numerous waterfalls.

For anyone interested, here is my in-depth Panama itinerary.

How many countries have you visited so far?

I actually don’t count, funnily enough!

What are your top 3 favorite cuisines?

My top three favorite cuisines are Italian (my paternal grandparents are from Italy), Japanese and Mexican.

What is your favorite restaurant in the world? What dish do you recommend there?

One of my absolute favorite dining experiences is doing the cocktail and food pairing menu at The Aviary in NYC and Chicago. It’s definitely not cheap, but the chef will surprise you with some incredible tastes. Bonus: Every cocktail that comes out is an experience, often interactive.

What is your favorite travel movie?

My favorite travel movie is Midsommar. It’s probably not what most people would consider a travel movie but I love horror.

What is your favorite international airport?

Honestly, I’m happy with any airport that accepts Priority Pass, as I usually hole up in the lounge to drink copious amounts of coffee and do work, or pretend I’m a bartender and make cocktails while relaxing.

Which city had the friendliest people?

You know, I often find that most cities are friendly once you share that you’re a visitor and you’re genuinely excited to be there and learn more about the place. And when you know the basic rules of how things work there.

For instance, in NYC my guests often tell me they’re surprised by how friendly New Yorkers are. I’m not saying we’re going to win an award or anything, but as long as you understand how to not get in the way of daily life — ie, don’t block the sidewalk to take an Instagram photo and don’t try to push into the subway as people are coming out — then we’re happy to help you.

Who is your favorite travel companion?

While I usually travel solo, I deeply cherish any trip I can do with my fiancé, Andy. So far we’ve done Italy, Panama, France and a number of US cities. We’ll be heading on a sustainable Galapagos cruise in October and I’m beyond excited!

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What is the best way to kill time while traveling?

As a travel blogger it’s rare I ever have true downtime. I could work forever. But I know this, so I will actually schedule in downtime!

What is the most exotic place your career has taken you?

The most exotic place I’ve ever visited is probably Bhutan. I’m yet to encounter a place with such a well-preserved culture that is so different from what I know as someone from New York.

What is your best bit of travel advice for someone who wants to, or is about to embark on a life of travel?

Don’t plan every single detail. Plan the very beginning of your trip, and leave room to let things just happen. You may meet other travelers who want to hang with for a bit, or maybe you learn about experiences you hadn’t heard of that you’d like to try. Leave room to allow these discoveries to take place.

What are 4 things you could never travel without?

Four things I could never travel without are my camera (because I’m a full-time blogger), my personal alarm (for safety), my scarf shawl (because it comes in handy for fashion, picnics and on cold planes), and a notebook (to unleash my creativity when travel inspires me).

What is your ultimate dream destination?

My ultimate dream destination, at least at this minute, is Tanzania, specifically to hike Kilimanjaro, see wildlife in Serengeti National Park, and relax on Zanzibar.

What is your favorite travel quote?

My favorite travel quote is “She believed she could, so she did” – R.S. Grey. I don’t think it’s traditionally a travel quote, but as a solo female traveler I think of it as one.

Where are you headed next?

My next trip is to explore historic England, specifically Chester, Lancaster and Carlisle.


Jessie Festa is a native New Yorker and owner of the solo female and offbeat travel blog, Jessie on a Journey as well as the online responsible tourism and culture magazine, Epicure & Culture. Since 2014, she’s been teaching online blogging courses to travelers wanting to make their dreams of location independence a reality. When not galavanting around the globe, you can find her leading photo tours in New York, taking yoga and hip hop classes, and sipping her way through the local cocktail scene.

In addition to checking out her blog, follow Jessie Festa’s travels by connecting with her on YouTube, Instagram, Facebook, Twitter, and Pinterest!

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