A journey is not just a destination, but an opportunity to grow, explore and reinvent oneself. There are no roads already mapped out for those who want to do something great. You have to build them yourself, one step at a time, with determination and passion
Kiara Di Paola is a travel storyteller, entrepreneur and licensed tour guide in New York City. Originally from the Marche region of Italy, Kiara moved to New York City over a decade ago, where she founded New York City 4 All, welcoming more than 11,000 visitors and offering unique tours that go beyond traditional tourist routes. Through her platform Kiariladyboss, she shares her adventures as a solo traveler, actively supporting women and local businesses. With over 520,000 followers on social media, Kiara inspires and guides women to travel safely and confidently, promoting the discovery of hidden gems in both New York and Italy. We interviewed her for TheNewyokese.
You arrived in New York almost by accident, turning that choice into an incredible opportunity, tell us how it all began.
My history with New York began in 2012, although I had already spent a month in the city in 2011 without being particularly impressed. The first time had been in 2003, with my father, but even then I was not fascinated. Yet, by a series of coincidences, I found myself living there. At first, I must admit, my heart was set on the West Coast, and Los Angeles seemed like my ideal place. But, surprisingly, it was New York City that chose me. It was not a bolt of lightning, nor a dream fueled by movies, but a bond born almost by contrast: at first I was trying to push it away, only to realize that while it was not my “ideal city,” it offered just the challenges, opportunities and that energy I needed. Before moving here, I had lived almost a year in Amsterdam. I was fascinated by the city of bicycles and the electronic scene that I loved so much, but I felt there was something bigger waiting for me elsewhere-something only New York could give me. So despite initial difficulties, I found that it was the city that would grow, challenge and inspire me, leading me to build a life I never imagined.
You are a travel enthusiast and a storyteller. How did you manage to turn your passion for the Big Apple into a successful business venture?
I have always been a traveler. I have explored the world solo, immersing myself in experiences that have shaped me. My first solo trip was an adventure to a faraway destination: Bolivia. The Salar de Uyuni, the largest salt expanse in the world, was my first big trip, a starting point that fueled my passion for discovery and made me realize how vast and rich the world is with stories to tell. New York gave me the opportunity to express a creativity I didn’t know I had. When I arrived, I was working as a babysitter and teaching Italian at Berlitz, a school with locations all over the world. Teaching has always been an important part of my life, thanks to my parents, both of whom were teachers. Telling and imparting knowledge was therefore a natural language for me. Over time, however, that passion turned into storytelling. I knew I wanted to work with people, and I had three key words in mind: audience, organization, travel. I didn’t yet know how to combine them, but I was certain that my work would have to intertwine these three elements.
You also created a successful brand, Kiara Lady Boss, what have been the challenges of building a business while creating a community that inspires other women?
When I started, the idea of a woman leading a business was not yet so common, and I had not considered it either. But New York taught me that I could be my own leader. The idea of opening a tour agency came almost by accident, thanks to a suggestion from a couple of friends on their honeymoon. I realized that the market lacked a supply of truly personalized experiences: there were many travel agencies, but few offered tailor-made tours. So I started doing research, contacting all the tour agencies and Italian tour operators present in New York and the United States to propose my project. It was not easy: I sent hundreds of emails, but only one agency considered my proposal. Without a portfolio, without a specific resume, without reviews, entering the market was a real challenge. Today I am the owner of New York City 4 All, a New York-based travel agency specializing in customized tours designed primarily for an Italian audience. I offer tailor-made experiences-both on foot and by other means-allowing each client to discover the city in an intimate and authentic way, away from the most common tourist routes, but able to capture the many facets of New York. In addition, I provide additional services such as airport transfers, English classes and passes to attractions, not only in the Big Apple, but also in major American cities. In parallel, I created the Kiara Lady Boss brand, where I share exclusive content that tells not only about the city, but also about my journey in the world of entrepreneurship. My goal is to inspire other women to follow their passions and turn them into a profession that fulfills them, just like I did.
How instrumental has social media storytelling been in growing your business?
As a content creator, vlogger and digital storyteller, I try to offer a perspective beyond the usual tourist descriptions, giving my followers an authentic and engaging experience. Social media has definitely been very important. In 2014 I was among the first content creators to do Facebook live: I was telling hidden corners of New York, local stories, and businesses that often escape the big tourist circuits, turning each tour into a unique, authentic, and highly personalized experience. The impact of storytelling played a key role in this journey. The ability to interact in real time with followers, to answer their curiosities, and to convey the essence of the city through my content has allowed me to create an active and passionate community. Storytelling, if done with passion and authenticity, can really make a difference and make each experience even more unique, thanks to the power of social media as a vehicle to reach a wider audience.
You have received major awards. How have they helped solidify your vision and commitment to telling the story of New York?
When I founded the agency my goal was to tell the story of New York in an authentic way, I never imagined that eleven years later I would receive prestigious awards and certifications such as the Media and Press Credential, the USPTO – United States Patent and Trademark Office or the coveted The Beacon Award 2023. In 2024, City Guide, one of the most influential publications on New York City, awarded me the Women in Tourism Award as “Tour Guide of the Year.” These awards not only fill me with pride but also push me to continuously improve.
Recently, I have also been involved in public speaking projects. For example, I had the opportunity to speak in front of an audience of 80 people on a fascinating topic, “How to Uncover the Soul of a City,” during the New York Travel & Adventure Show. It was an enriching experience that allowed me to explore the deep connection between cities and the stories that animate them, offering a reflection on how each urban corner can reveal a part of its soul through its culture, traditions and the people who live it. Each milestone achieved is a piece of an ever-evolving journey that motivates me to continue telling stories capable of inspiring and engaging anyone who chooses to discover this extraordinary city.
What do you think is the added value of your agency and services?
My added value lies in my ability to offer tailor-made experiences, allowing travelers to experience the city not as mere tourists, but through the eyes of those who really live there. It’s not just about visiting New York, but feeling its rhythm, discovering its lesser-known sides and accessing exclusive events and venues thanks to my insider tips. Another distinctive element is my team. The people who work with me are true rock stars, professionals with unique personalities and a free and authentic approach. We don’t offer simple pre-packaged tours, but 360-degree immersive experiences. Each guide has his or her own style, a personal point of view, and above all a passion for storytelling. We do not follow rigid scripts, we adapt to the client’s needs, and sometimes we even become a bit of a situational psychologist! For us, travel is connection with the city, with the stories we tell, and with the people we accompany, who often become friends or even family. My tours are not for everyone, and I say that without hesitation. My audience is made up of curious, humble travelers, people who love to discover the world authentically. Some are experienced travelers, some are novice travelers, but they all share a common desire to explore with awareness. My clients are between 13 and 80 years old, so it is not a question of age, but of mindset. Those who expect to find the perfect espresso like at home are probably not the type of traveler for my tours. In the past I often used to say “experience the city like a local,” but today I avoid that expression because it has become a cliché. What I offer is not just a “local” experience, but a trip with a guide who has an authentic connection to the place and knows how to convey that through social media, the website, and reviews. In the end, what I really care about is leaving something more than just a memory. I would like those who travel with me to bring with them a new, more conscious and respectful approach to travel. If one day my clients were anywhere in the world, I would want them to think, “Kiara said it’s important to support local realities. Let’s go there instead of the usual tourist places.” If that happened, I would know I had really made a difference.
The article Kiara Lady Boss: From passion for travel to entrepreneurship comes from TheNewyorker.
