2025 Woman of Influence: Stacey Ray

Stacey Ray, Founder & CEO, Sisterhood Travels and Podcast Host, Life. Reimagined. with Stacey Ray, is a 2025 Woman of Influence, an initiative by Groups Today that celebrates the dynamic women shaping the group travel industry. Whether they're mentors, visionaries or brilliant leaders, their contributions deserve to be honored.

Stacey Ray is a powerhouse in women's group travel and the founder of Sisterhood Travels, a transformative movement redefining how women 45 and up explore the world. With bold vision and unwavering passion, she has empowered thousands of mature women to travel fearlessly, often turning first-time travelers into lifelong explorers. Her expertly curated journeys foster deep connection, personal growth, and lasting sisterhood.

Ray's influence is reshaping the industry—creating spaces where women feel seen, supported, and inspired to claim the world as their own.

Groups Today: What does it mean to you to be a woman leader in the group travel industry?

Stacey Ray: Honestly, being recognized as a woman leader in this industry feels incredibly validating. As the founder of a women-owned and -operated travel company that focuses on women 45 and up, it means so much to stand out in a space that's traditionally been led by big, often male-run corporations.

What really makes us different and what our travelers connect with most, is that I am the woman we serve. I know what they're dreaming about, what scares them, and what they're craving from life, because I've been there too. That kind of realness is the heart of everything we do. We lead with empathy, we lead with purpose, and we've created something truly special: a space where women feel seen, heard, and empowered to explore the world on their own terms.

This kind of recognition just reinforces what I already know in my heart: that our work matters. And that creating space for women, by women, has real power.

GT: How would you describe your approach to leadership?

SR: For me, leadership is all about purpose, integrity, and collaboration, and that touches everything I do, whether it's with my team, our travelers, or the industry as a whole.

When it comes to my team, we start with hiring people who are truly aligned with our mission. I'm a big believer that you can teach skills, but you can't teach character. And after years in corporate America, I've grown into a much more collaborative leader. I've learned to really value inclusion and trust, and I try to lead by example: open, imperfect, and putting people first.

With our travelers, leadership means honoring their stories. A lot of these women are in a place of transition. Maybe dealing with loss, starting over, or simply learning how to take up space again. I see it as my job to encourage and guide them, to help them remember just how capable and amazing they are. We don't just plan trips; we help women come home to themselves.

And on the industry side, I lead with intention. I'm proud to challenge the outdated ways of doing things, especially when it comes to how women 45 and up are represented and served. I want to keep raising the bar and showing that leadership doesn't have to follow the old rules to be powerful.

GT: How do you use your influence to better the group travel industry?

SR: I use my voice and my platform to shake things up especially when it comes to how mature women are treated in this space. For way too long, traditional tour operators have used the same cookie-cutter models that just don't reflect what today's women 45 and up really want. These women are looking for something deeper than a sightseeing checklist. They want connection, authenticity, intimacy, and a sense of belonging.

That's why I created Sisterhood Travels. Our small, women-only groups are about real friendships and life-changing experiences. We're not just booking trips, we're building a movement where women get to show up as their full, unapologetic selves.

And we're not stopping there. Behind the scenes, we're actively pushing for things like eliminating those frustrating and cost prohibitive single supplements, fighting for fairer pricing for smaller groups, and partnering with women-owned businesses around the world. This isn't a trend. It's a shift. And I'm proud to be helping lead it.

GT: What are some of your favorite accomplishments so far?

SR: There's nothing that fills me up more than seeing a woman who's been through something hard such as loss, fear, or a big life change, step onto one of our trips, hold her head high, and say, "I can do this." That one brave moment? That's everything. That's why we do what we do.

What started as a mission has truly turned into a movement. These aren't just vacations. Rather, they're journeys back to joy, confidence, and self-worth. I'm so proud that Sisterhood Travels has grown way beyond what I first imagined. I started with a small private Facebook group of 250 women and have expanded to a global community of over 45,000 and all without a single ad. That kind of organic growth? It speaks volumes about what we're building together.

Another moment I cherish is launching our podcast, Life. Reimagined. with Stacey Ray. It's raw, real, and full of stories from women who've turned life's detours into new destinations. It's become such a beautiful extension of our community and every time a listener tells us, "I feel seen," I know we're doing something right.

GT: What impact do you hope your work will continue to have on clients and peers?

SR: More than anything, I want women, especially those 45 and up, to know that their story isn't finished. There's still so much to explore, to feel, to dream. I want them to feel empowered, connected, and supported. To know they're not alone. That there's a whole sisterhood out there cheering them on.

For others in the travel industry, I hope to inspire a bigger shift. One that chooses heart over hustle. That focuses on connection, meaning, and inclusivity, not just profit or tradition. Group travel can be so much more than just logistics: it can transform lives when done with intention and love.

GT: As a woman entrepreneur in group travel, what challenges have you faced—and how have you overcome them?

SR: Oh, where do I start? One of the hardest things has been just getting taken seriously. Not only by men but sometimes by other women too. There's still this weird disbelief that a woman-owned business serving mature women could possibly be successful or influential. But here's the thing: I know the value we bring, and I'm not here to convince people who don't see it. I've learned to walk away from partnerships that don't align with our values and that boundary has served both me and our community really well.

And yes, I've dealt with copycats. Big companies that think they can just slap a "women-only" label on their trips and replicate what we're doing. But they always miss the heart of it. Sisterhood Travels isn't a marketing gimmick. It's a soul-centered movement built on real relationships, trust, and intention. That's not something you can fake.

I stay focused on what matters: listening to our community, protecting the magic we've built, and leading with integrity. That's how we keep moving forward.

GT: What's your personal mantra—or travel philosophy—that guides your work?

SR: "If not now, when?" That phrase has been a constant in my life—and it's what I share with the women we serve. So many of them have spent their lives putting everyone else first. This is their time to finally say "yes" to themselves: "yes" to adventure, "yes" to joy, "yes" to being fully alive.

I also believe that travel is just as much about discovering yourself as it is about discovering the world. It challenges you. It expands you. It shows you who you are and what you're capable of. I always say: "What's the difference between an obstacle and an adventure? Attitude." That shift in mindset can change everything.

And above all, I believe we have a responsibility to give back more than we take. Whether it's by supporting women-owned businesses, respecting local cultures, or traveling responsibly—we aim to uplift the places and people we visit. That mindset guides every decision we make. Because we're not just travelers: we're part of a global sisterhood, and we're here to leave things better than we found them.

GT: What are your goals for the future?

SR: Looking ahead, my goals are all about expanding our mission and making an even bigger impact not just through travel, but through purpose-driven community and advocacy.

I want to keep aligning with organizations and global initiatives that share our belief that women over 45 are anything but invisible—they are invincible. This next chapter is about redefining what's possible as we age. There's so much more life to live, and we're just getting started.

I also see our community growing through deeper partnerships, more off-the-beaten track itineraries, storytelling, and more exciting adventures. Our podcast is a big part of that, and I want to keep using it as a way to amplify women's voices and inspire change.

Ultimately, I want to keep pushing the industry forward. I want to help reshape group travel for our demographic by making it more intentional, more inclusive, and more reflective of who we really are. My dream? To spark a global shift in how mature women see themselves and how the world sees them one unforgettable journey at a time.

The 2025 Trailblazers of Group Travel: Women of Influence Special Report originally appeared in the Sept/Oct '25 issue of Groups Today.

Edited by Sarah Suydam, Managing Editor for Groups Today.