Today we’d like to introduce you to Samantha Casolaro.
Hi Samantha, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
Hi, I’m Samantha Casolaro. I’m 26 and I’ve been traveling the world solo for the past 3 years to over 34 countries! I didn’t grow up traveling and had no idea where to even begin. After graduating from UNC Chapel Hill in 2022 from the MEJO school, I booked a one-way ticket, planning to explore for three months before starting a “real job”… spoiler alert I never stopped.
I am now a travel content creator and group trip host, with 47K followers on my Instagram, @samanthacasolaro, and 151K followers on my TikTok, @travelingwithsamantha. As I learned how to navigate solo travel on a budget, I kept meeting girls who wanted to do the same, but didn’t want to figure it all out alone. I was approached by a group trip company and NEVER thought I could sell a trip to my audience. Because who was I to host a group trip? I put myself out there and my first two trips to Costa Rica sold out in SEVEN seconds. I was in shock. So in January 2024 I hosted one group trip. Then another. Now, over 350 +women have joined me across 20 trips in 10 countries!! I created this community to make solo travel feel less intimidating and more empowering: with support, connection, and built-in friends from day one.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It has not been a smooth road. I did not grow up traveling or even thinking about the idea of it because I never thought I could afford it. I’m a SNAP kid, a FAFSA kid and a kid who had such an unstable family background (raised by addicts, low income and food insecurirty, etc) growing up that I am surprised I made it to college, let alone another country! While going to UNC I was under the Carolina Covenant plan after transferring from community college. This allowed me to go to college debt free and also paid for my passport!! I would not be where I am today without this, I had no idea how I was going to afford school. Through UNC, I was inspired to study abroad and applied to endless scholarships tp be abke to go to fashion school in London. This is what started it all for me. UNC & other donors supported my way through a semester at London. It’s there I took my first solo trip alone to Greece after being TERRIFIED to go alone but it was my dream. I cried for weeks to anyone who would listen that I was too scared to go alone but it would be a regret if I didn’t. Everyone thought going alone would be insane but I did it anyways and it was the biggest shift in my life possible. I cried the whole way, but I met friends immediately, some I still talk to to this day. I met 3 women who told me they travel full time, my repsonse being “WHAT DO YOU MEAN?” I had never heard of that concept, I thought they must have family money to travel like that. They each had their own unconventional lifestyles that led them here, and it changed somehting inside me and lit a fire. I had no idea how I was going to make that happen, but my mind knew I would. I finished my last semester after this trip in the US at UNC and after graduating I told everyone I would just go on ONE solo trip to Europe for 3 months and then I would go back and get a “real” job like I am supposed to. Well… that did not happen.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I am a solo travel content creator sharing tips for women to travel safely and run group trips and create experiences that bring together amazing women from all over the world. I have hosted 20 group trips across 10 countries with over 350 stragers turned friends so far. We have done things like island hopping in Thailand, going on a safari in South Africa, visiting a world wonder in Brazil and Peru, taking a ramen making class in Japan, hiking a volcano in Guatemala and more!
The ages have ranged from 18-52, the usual guests are 20-32 but there have been outliers and it makes it so fun! No matter the age, everyone is there to have a fun time and build friendships while exploring the world so it always works out. What started as a love for travel has turned into building a community where people can step outside their comfort zones, make lifelong friendships, and explore places in a way that feels authentic and meaningful. I handle all the logistics with companies so everyone can just show up, be present, and enjoy the experience. More than anything, I focus on the connections that happen during the trip. By the end, strangers usually leave feeling like lifelong friends, and that’s honestly my favorite part. I have seen complete strangers on day one become best friends and travel partners by the end and still see so many girls having reunions across the globe years later!
What I’m most proud of is the community that’s grown from it. Watching women come on a trip nervous and leave with new confidence, beautiful memories, and friendships they never expected is something I’ll never get tired of. Some of the people who’ve met on my trips have become best friends, travel buddies, business partners, and even roommates.
I think what sets me apart is that I genuinely care about every person who joins. It’s never just about seeing beautiful places, it’s about creating an experience where people feel welcomed, supported, and inspired. I want every trip to feel like traveling with friends rather than being on a tour, and I think that’s what keeps people coming back. I have SO many repeat guests which makes the trips so much more special because I know I did something right. My trip to Egypt this year is 95% return guests which is insane!! All the worlds colliding where everyone can meet will be so much fun.
I want my trips to be a space where people can leave their home life and home or any of their problems and they can come and have fun, be with a supportive group of women who make them feel heard and not alone and enjoy beautiful countries without fear or loneliness. The trips are also often budget trips, some trips having only hostels and some with hotels and it makes it so much more accessible for countries that are difficult to go alone to as a woman or that are more expensive!
Another lesson I’ve learned is the power of vulnerability. For a long time, I only shared the highlight reel, but opening up about my upbringing, my experiences, and surviving sexual assault changed everything. It was scary to be that honest, but I realized people connect with authenticity far more than perfection. By sharing my story along with practical travel safety tips and ways to help others feel more confident exploring the world, I created something much deeper than a social media following, I built a community. People knew they had a place where they felt seen, supported, and understood, and that’s something I’ll always value more than numbers. At the end of the day, I don’t measure success by how many people follow me. I measure it by the connections that are made, the confidence people gain, and the community we’ve built together and that’s the part I’m most proud of 🙂
What would you say have been one of the most important lessons you’ve learned?
The most important lesson I’ve learned is that community, especially community with women, is everything. Travel is amazing because of the places you get to see, but it’s the people you meet along the way that truly make it unforgettable.
I’ve realized that when you create a space where people feel comfortable being themselves, amazing things happen. I’ve watched complete strangers become best friends, start businesses together, support each other through life’s highs and lows, and continue traveling together long after one of my trips has ended. I have learned that with the right women by your side, anything is possible. That has completely changed how I look at what I do. I’m not just planning vacations, I’m creating opportunities for genuine connection and friendship to continue beyond each country in hopes it brings more people together. At the end of the day, the destinations are beautiful, but the community people build is what lasts long after everyone gets home. That’s the part I’m most passionate about, and it’s the reason I keep doing what I do. Knowing I have inspired even one woman to get out in the world and travel without waiting on anyone else, especially a romantic partner, keeps me going and makes me proud.
Pricing:
- Trips range from $1300-$3000 depending on location, season and types of accommodation (hotels/hostels)
Contact Info:
- Website: https://samanthacasolaro.my.canva.site/travelingwithsamantha-group-trips
- Instagram: https://www.instagram.com/samanthacasolaro/?hl=en
- LinkedIn: https://www.linkedin.com/in/samanthacasolaro
- TikTok: https://www.tiktok.com/@travelingwithsamantha
