Ally Pintucci of The Girls Trip Series Is Changing the Way Women Experience Solo Travel

Helping shape the way people and brands show up online (and IRL). Ally Pintucci is a Vancouver-based commercial photographer, creative director, and community builder whose work captures stories for notable global brands, real people, and beautiful places around the world.

Known for a refined, story-led approach to brand building, she works with both local teams and globally recognized brands to help them connect more meaningfully with their audiences — creating elevated visual and campaign assets rooted in place, people, and experience. Her work is thoughtful, collaborative, and grounded in storytelling that feels as considered as it is accessible.

As the founder of The Girls Trip Series, Ally leads an ever-growing community of women through meaningful travel experiences. She also brings warmth and presence to her work as a host and speaker, creating spaces that spark genuine connection and conversation.

ALLY PINTUCCI, THE GIRLS TRIP SERIES, HELEN SIWAK, PORTFOLIOYVR, VANCOUVER, BC, YVR

COMPANY BIO

The Girls Trip Series is a global travel and social club designed for the solo female traveller who craves connection with like-minded women, without the rigidity of traditional group tours. Founded by Ally Pintucci, the brand curates intimate, design-forward trips for women in their thirties to fifties who are done waiting on others to see the world.

Born from a decade of experience in the travel industry and a firsthand understanding of what was missing for women travelling solo, The Girls Trip Series was built to remove the friction that keeps meaningful travel from happening. Schedules that never align, friends in different life stages, the uncertainty of group dynamics — the Series solves for all of it. Retreats felt too structured, tours too rigid. What Ally built instead is something more considered: small, curated groups, thoughtful itineraries, genuine cultural immersion, and a community that forms before the trip begins and lasts well beyond it.

Eleven adventures across the globe have reinforced what the concept set out to prove — that connection is as compelling as the destination, and that the right group of women can make anywhere extraordinary.

ALLY PINTUCCI, THE GIRLS TRIP SERIES, HELEN SIWAK, PORTFOLIOYVR, VANCOUVER, BC, YVR

IN HER WORDS

There was no single defining moment. Looking back, that feels important to say — because the story of how I got here is really the story of paying attention over a long period of time. Working across sales, operations, brand, agency work, and eventually photography in both Toronto and Vancouver, I kept collecting lenses. Each role showed me something different about how businesses run and how brands connect with people. What I noticed, slowly and then all at once, was that I was most alive when I had ownership over my work, creative freedom, and the flexibility to choose who I worked with and where I worked from.

That realization pushed me to go freelance in 2018. Agency life was not the right fit, and I wanted to build something more aligned with how I actually wanted to work and live — collaborating with local teams and global brands, creating thoughtful, story-driven work on my own terms. The decision felt natural by the time I made it. I like to say I traded one boss for fifty. It suited me perfectly.

BUILT ON EARLY FOUNDATIONS

My mother shaped my entrepreneurial thinking before I had language for it. She did not believe in sitting around, and she brought me into her world early — having me help with office administration when I was still young. It gave me a foundational understanding of how businesses operate behind the scenes, long before I ever worked in one officially.

As a teenager, I worked as a camp counsellor and in community programs with the City of Toronto. Those roles taught me how to lead, adapt quickly, and connect with genuinely different kinds of people. I went straight into the workforce at eighteen, and what was meant to be a gap year turned into nearly a decade in the travel industry. I learned how to sell, plan, problem-solve, and create experiences that actually resonate. I learned, above all, how to read people.

Launching The Girls Trip Series felt like a full-circle moment — returning to the travel industry, but this time on my own terms, with everything I had built in brand, photography, and community folded into something I could take around the world. Those early jobs never felt small. They built the foundation for everything I am doing now.

ALLY PINTUCCI, THE GIRLS TRIP SERIES, HELEN SIWAK, PORTFOLIOYVR, VANCOUVER, BC, YVR

THE WORK THAT CONFIRMED IT

One of the first real shifts in my perspective came from booking a $20,000 photoshoot. As a young aspiring travel photographer, that number felt surreal. Being flown around the world to shoot for brands like Four Seasons and Air Canada validated something I had been quietly building toward — that I could operate at a high level while doing work I genuinely loved.

But launching The Girls Trip Series has been the most meaningful milestone by far. The first trip exceeded every expectation I had. Watching women open up, form real friendships, and share how profoundly the experience had moved them was something I had not fully anticipated — and something I have never stopped being grateful for. Eleven adventures later, that feeling has only deepened. The business side matters, but what stays with me is the human side — the connection, the growth, the shift you can actually witness in real time. Even on the trips that lost me money, I have never once questioned whether this is the right work.

LEARNING TO RIDE THE WAVE

My entrepreneurial journey has been anything but linear. I often compare it to something people say about healing — it does not move in a straight line. There are highs where everything clicks, and moments where you are forced to adapt faster than feels comfortable.

The pandemic disrupted the business significantly, and global events continue to affect travel in real time. When your work is tied to industries like travel and hospitality, you feel every shift immediately. Early on, I believed success came from having a clear plan. What I have learned instead is that resilience and adaptability matter far more. I have had to get comfortable making decisions with incomplete information and trusting my ability to pivot.

Before the pandemic, I launched a small agency. When COVID hit, most clients paused or pulled budgets overnight. Rather than forcing something that was not working, I returned to freelance and focused on my own clients and flexible contracts. I also launched a podcast, Unfiltered with Ally Pintucci, which surpassed fifty thousand downloads before I made the difficult decision to end it — one I still think about. Every one of those chapters, including the ones that did not go as planned, led me to where I am now.

ALLY PINTUCCI, THE GIRLS TRIP SERIES, HELEN SIWAK, PORTFOLIOYVR, VANCOUVER, BC, YVR

WHAT SOLO COSTS

The biggest sacrifice has been stability. When you work for yourself, there is no guaranteed income, no clear path, and no real off switch. I have run trips while sick, managed logistics on the road while completely depleted, and dealt with homesickness while still needing to show up fully for the women in my care. The mental load does not simply turn off because you are somewhere beautiful.

It can strain personal relationships too. The schedule is unconventional, and there are times you are physically present but still working, or missing things because you are away. I will not pretend that is easy, because it is not.

What it has given me, though, is equal in measure. It has made me more resilient, more self-reliant, and more intentional with my energy. Balance is not something I have perfected. It is something I am constantly adjusting. But I have learned how to make space for both meaningful work and the relationships that matter most, and that ongoing negotiation has made me someone I am genuinely proud to be.

THE GIRLS TRIP SERIES

I did not start The Girls Trip Series with a master plan to build a massive company. Honestly, I did not think the world needed another tour option — there are already so many. But as a solo traveller with over a decade in the industry, I kept feeling that something was missing for women like me.

Solo travel is easy when you are younger. You meet people effortlessly and everything feels social. As you get older, those environments do not always fit, and while solo travel can be deeply fulfilling, it can also feel isolating. I found myself wanting to share meaningful experiences with someone — but the existing options did not feel right. Retreats were too structured, tours too rigid, and there was always uncertainty about the group dynamic.

What I built instead are small, curated trips for women in their thirties to fifties who want genuine connection without feeling stuck. The friction of getting friends to align — mismatched schedules, different life stages, careers, relationships, families — is removed entirely. I curate the group, hold the space, and create the conditions for something real to happen. It is not about checking off destinations. It is about how you feel while you are there, and who you become when you go.

THE LEGACY BEING BUILT

Legacy, for me, is measured in the women who leave each trip carrying something they did not arrive with. A friendship they did not expect. A version of themselves they had not yet met. A memory that belongs entirely to them.

The world is becoming more digital by the day, and I believe women are craving real, in-person connection more than ever. That is not a trend I am chasing — it is the foundation of everything I have built, and it is what I intend to keep building. I am seeking aligned brand partners and tourism boards who value connection-driven experiences, sponsors who can contribute both budget and creative collaboration, and support for scholarship initiatives to make travel more accessible. Longer term, I am building a team across content and operations, and a network of aligned hosts to expand The Girls Trip Series globally — while protecting the experience that makes it what it is.

The legacy I am working toward is a world where women do not wait for everything to line up before they say yes. They show up, they connect, and they come home.

Author Profile

Helen Siwak, Collaborator: This story is created in collaboration between Helen Siwak and the featured subject. As the founder and publisher of Portfolio.YVR Business & Entrepreneurs Magazine, Helen works closely with entrepreneurs to share their paths of innovation, resilience, and growth. Each story in this series is co-developed through interviews and first-person insights, blending authentic voices with Helen’s editorial expertise to highlight the remarkable individuals shaping British Columbia’s business landscape.