Matador Creators Spotlight: Sara Iannacone on Launching a Freelance Writing Career

Matador: Tell us a little about your background and what you feel sets you apart from other travel writers and content creators?

Sara Iannacone: I’m a travel writer and multi-passionate entrepreneur driven by a deep love for exploration and storytelling. What sets me apart from other travel writers and content creators is exactly what I’ve made myself wrong for in the past—I don’t fit into the proverbial box society expects us to fit into, and my career hasn’t been a straight upward trajectory.

For a while, I was embarrassed by how many different lives and careers I’ve had since graduating with a tourism and hospitality management degree. But now, I believe every experience I’ve had—from working in global hotels and events to building a copywriting business to getting certified in life coaching and Reiki—has set me up for success in this field. Every experience was centered around exploring, paying attention to the details, asking great questions, and presenting a meaningful final product on time, every time. All of which serves when you’re a freelance travel writer.

On a recent press trip to El Cielo Resort & Winery in Valle de Guadalupe, Mexico, I was invited to blend my own wine! I named it La Buena Vida, which means The Good Life. Photo: Sarah Iannacone

How did you initially hear about Matador Creators and land a press trip?

I’ve been a Matador reader for years, yet I had never thought of pitching my work. But, last spring, I was chatting with travel blogger Jackie Carbo right after I had returned from a trip to Mexico. She recommended I check out the Matador Creator portal because there was a call for pitches for stories about luxury hotels in Mexico.

That little push was exactly what I needed to craft my first editorial pitch, and much to my delight, it was accepted. Writing that first piece, I realized just how much I loved editorial writing, and I decided to pursue more of it after it was published.

From there, I started pitching press trip opportunities on the Matador Creators portal that aligned with my expertise and interests. This meant mostly hotel-centric press trips or anything in Latin America. I pitched five or so before I landed my first one in October 2023 and have been on a few since.

I’ve made my beat Latin American hotels, cuisine, and culture, so I get to eat a lot of incredible street food during my travels. This was a food tour in Mexico City. Photo: Sarah Iannacone

How long have you been working with travel brands and media, and how did you get started?

The short answer: about a year. The long answer is a little more complex.

When I was in school for tourism and hospitality management, I ended up in global events, hotels, and marketing for over a decade. During that time, I was the one seeking press and media coverage for my properties, events, and clients, which gave me a different perspective on the industry.

During COVID, I knew I wanted to change my path when the events industry took a hit. So, I put my marketing skills to work and started a copywriting business, which took off and allowed me to work for myself.

Then, last year, the introduction of AI and other technology impacted the copywriting industry greatly, and I wanted to start focusing on writing that couldn’t be replicated, which led me to travel writing and journalism.

This elephant sanctuary excursion in Chiang Mai, Thailand, opened my eyes to ethical and sustainable tourism, which I try to incorporate into my writing as much as possible. Photo: Sarah Iannacone

What tools do you rely on most when creating your travel content?

I’m very much a writer and not a content creator, so my tools are probably a little different than those who are super talented with social media and content creation.

There’s a fine line between being present on a trip and taking notes so you remember the little details for the article. For that reason, my phone is my only real tool.

I send myself voice notes in Voxer after an experience, and I will also take notes on the Notes app on my iPhone if I’m with a source. I just let them know I’ll take notes before so they know why I’m on my phone during an experience. Finally, if want to remember the sounds or vibe of a place, I’ll take a quick video so I can get myself back to that place mentally while I’m writing.

How has working with Matador helped your work in travel?

My work with Matador is what gave me my big break in the travel writing industry.

Through my first couple of Matador Creator trips, I was able to create really strong relationships with different public relations (PR) companies, tourism boards, hotels, guides, and editors. These relationships have all led to many other opportunities, for which I’m grateful.

Plus, other PR companies have found my articles on Matador and invited me to work with them. From that, I’ve been able to write about even more experiences for Matador and other outlets, so it’s come full circle recently.

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A post shared by Sara Iannacone 🌎 Travel Journalist & Life Coach (@onewanderfullife_)

What advice would you give to someone interested in becoming a travel writer or travel content creator?

Three things: create relationships, ask questions, and keep pitching through rejection.

This industry is entirely relationship-based. Once you have connections and relationships, everything starts to flow. When you’re in the room (literal or figurative) with someone from a PR company, a tourism board, other writers or creators, etc., ask questions!

Ask about their process, what other clients they work with, and how they operate. The more you know, the easier it will be to tailor your pitches to address all the important points, which ultimately will get them accepted.

Initially, it can be discouraging when you’re getting a no or radio silence with every pitch. I’ve heard many people quitting before they catch their big break because it was too difficult to handle so much rejection. Just know that the rejection or lack of response means nothing about you or the quality of your work. With the right timing and pitch, you’ll land your first gig, and it’s a snowball effect from there. Be patient. It’s worth it.

In your opinion, what are some of the biggest misconceptions or challenges about being a travel writer or content creator?

I think the biggest misconception is that you’re just on vacation all the time. Press trips are packed with activities, and it can be difficult to manage deadlines and client work while you’re on a trip. Often, you’ll get the itineraries pretty close to your actual departure date (we’re talking days in advance, not weeks), so it can be difficult to plan and manage your workflow.

Making travel writing profitable when freelancing and not working in-house at a publication is also challenging. You’re most likely not going to become a millionaire. I like to say you get paid more in experiences. This can be pretty incredible but hard as well. Most of the time, your expenses are covered, but you’ll still have to pay for parking at the airport or miscellaneous items. This adds up when you’re only getting paid $200-$400 per article on average. It becomes a volume game to make money, and that’s a lot of work that oftentimes can lead to burnout quickly.

A lot of freelance travel writers I know also do freelance copywriting work and/ or have another business to make ends meet. I have a life coaching and Reiki business that supplements my income so I can continue to do travel writing and cover the associated costs without having to hustle 24/7 to get articles and pitches picked up. It makes it more fun when you can take a bit of the financial pressure off in other ways that fill your cup, too.

What are a few recent stories you’re particularly proud of?

”Seafood, Sustainability, and Sunsets: the Basics of Baja California Sur, Mexico” for Matador Network: I fell in love with Baja California Sur on this trip, and it was an honor to write about such an unrivaled destination. There was something about the guides who showed me the area, the individuals who hosted me, and the unimaginable landscapes and scenery that made this place feel like one of the most special in the world. I think everyone should experience it once in their lifetime, and I hope this article inspires people to visit and explore it for themselves. No lie, I still dream of this trip every single week almost eight months later; it was life-changing.

”Traveling With Depression: The Strategies That Help Me Make the Most of Every Trip” for Conde Nast Traveler: Writing about the intersection of mental health and travel is a top priority for me. Mental health struggles have been a part of my story, but I’ve made sure that they don’t define me or hold me back from what I want to do—especially when it comes to travel. I want to inspire others who may be struggling to continue to chase after their dreams, even on the hard days. While I’ve written about my story before in smaller publications, writing this for Condé Nast Traveler was huge for me in terms of vulnerability and impact.

”We paid $781 a night to stay at an all-inclusive resort in Mexico. These 6 things made our weeklong trip an excellent value” for Business Insider: This was the biggest publication I’ve pitched to date in terms of monthly readers, and I got my first pitch accepted. It was the first time I felt like I had mastered the art of pitching, and it challenged me with a new style of writing, as Business Insider’s voice and style are super different from other publications.