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.
Ragan Andrew, CTP, Owner & Travel Curator, Adrift Tours & Travel, 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.
Shirley Davis Conner, CTIS, CSTP, TMP, CHME, Principal, Conner Hospitality Consulting and Executive Director, Metro Memphis Attractions Association, 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.
Shirley Davis Conner got her start in hospitality as a hotel front desk clerk during college. Later, when working in both operations and sales at hotels and attractions, she was tasked with learning about the group travel industry and has never looked back!
A native Memphian, Davis Conner quickly learned to share her love of the area by building interesting itineraries so motorcoach groups would visit not only Graceland, but also many of the other great attractions throughout the Mid-South. Her career now includes working with clients to promote group travel throughout the Deep South, as well as Upstate New York.
Groups Today: What does it mean to you to be a woman leader in the group travel industry?
Shirley Davis Conner: The group travel industry is so fun and rewarding that I can't imagine working in any other industry. It's an honor to be named a woman leader in the industry that I love.
GT: How would you describe your approach to leadership?
SDC: I strive to lead by example. I don't ask anyone to do something that I'm not willing to do myself. I believe in helping others grow by sharing my experiences and then giving them the freedom to try things for themselves.
GT: How do you use your influence to better the group travel industry?
SDC: An early boss taught me the value of being involved, so I volunteer at conferences, I join associations, and I network with others every chance I get. I believe in staying involved and staying current and I encourage others to do this as well. The more we can learn from each other, the stronger our industry will be.
GT: What are some of your favorite accomplishments so far?
SDC: Two projects I worked on when I was with Graceland were my favorites:
1. I helped to start the annual Scouts Rock at Graceland event which introduced Boy and Girl Scouts (and their families) to Elvis and promoted visitation to our partner attractions in the Memphis area.
2. I was able to start Graceland Excursions—day tours that took visitors outside of Memphis, into the Mississippi Delta and to Tupelo. We wanted everyone to experience Graceland and Memphis, but we also wanted them to learn more about the region. There's so much to see! Both projects were all about partnering with others to create more opportunities for visitors to the region. A rising tide lifts all boats!
GT: What impact do you hope your work will continue to have on clients and peers?
SDC: My goal is to be a connector. I want to encourage others to network and have the conversations that will help them figure out how they can work together to bring business to each other's bottom line.
GT: What's your personal mantra—or travel philosophy—that guides your work?
SDC: My parents were my biggest influence. "Keep your chin up," were the words of wisdom I learned from my dad, so I try to find something positive in all situations.
"Tough times never last but tough people do," was a saying I heard from my mom growing up. That taught me that no matter what the situation is, I can keep going because I'm going to learn from whatever is going on around me and come out stronger because of it.
Life is a journey so get out and explore! This one helps me to remember not to remain stagnant and to reach beyond my comfort zone because there is always something new to learn.
GT: Where does your passion for Memphis come from?
SDC: I was born and raised in Memphis and took my first solo trip on a Greyhound bus when I was in high school. I clearly remember traveling back across the bridge over the Mississippi River and seeing the Memphis skyline after being gone for two weeks. It was such a beautiful sight that I though then, and I still do now, THIS IS MY HOME! I now live in a suburb outside of Memphis that just happens to be in the beautiful state of Mississippi. No matter where I travel in the world, I'm always thrilled to get back home to Memphis and the Mid-South region.
GT: What are your goals for the future?
SDC: I want to continue to explore the U.S. and beyond, connecting with my travel friends and family I've made through the years of being in the industry, and I want to introduce my grandchildren to my love of learning through travel.
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.
Sandy Borowsky, Owner, EVP Tours, Starr Bus Charter & Tours, 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.
Sandy Borowsky is a dynamic leader in the motorcoach and group tour industry, serving as Executive Vice President and third-generation owner of Starr Bus Charter & Tours. With over 25 years of experience, she has grown Starr's tour division, launched the successful College Break Bus program, and forged meaningful and long-lasting industry partnerships.
A respected voice in tourism, Borowsky is known for her innovation, industry involvement, and commitment to creating unforgettable travel experiences for thousands of loyal customers each year.
Groups Today: What does it mean to you to be a woman leader in the group travel industry?
Sandy Borowsky: In an industry traditionally dominated by men, I'm proud to be part of the strong, hardworking group of women who are leading the way forward.
Being a woman leader is especially meaningful to me as a mother of three young men who have grown up seeing a woman in a position of leadership. For them, it's normal—and that gives me confidence they'll support and champion women as they build their own personal and professional lives.
GT: How would you describe your approach to leadership?
SB: To me, leadership is about bringing people together and working side by side toward a common goal. I'm incredibly lucky to have a team that's talented, dedicated, and passionate. My success as a leader is really our success—because I don't do this alone. I'm in it with them every day, supporting, listening, and problem-solving together. That kind of collaboration is what makes this work so fulfilling—and what makes real progress possible.
GT: What are some of your favorite accomplishments so far?
SB: One of my proudest accomplishments is successfully transitioning Starr to its third generation alongside my husband and partner, Pete. It's been incredibly meaningful to carry our family business forward—especially navigating it through the pandemic.
I'm also especially proud of starting and growing College Break Bus, a transportation service that helps students get home and back to school during academic breaks—while keeping countless cars off the road and making life easier for families. It's been a fun and rewarding journey—and on those busy move days, there's never a dull moment! Watching that program thrive has been one of the highlights of my career.
GT: What advice would you give to other leaders of generational businesses, and how has your family's legacy shaped your personal vision for the company?
SB: My biggest advice to leaders of generational businesses is to build trust and prioritize open communication with your family members. Don't assume anything—talk about it. And don't set expectations without having clear conversations.
Just as important: Connect with others in similar situations. There's so much value in learning from peers who understand the unique challenges of running a family business. You're not alone—and those shared experiences can be incredibly helpful.
For me, our family's legacy is Starr's foundation—but my vision is about building something even stronger into the future.
GT: How do you balance running a business with your spouse and what advice do you have for others who may be considering doing the same?
SB: Working with your spouse definitely has its challenges, but for us, it really works. We balance each other out—we each have different strengths, and we trust and support each other no matter what. We've figured out how to stay in our own lanes when needed and when to team up. And honestly, we laugh a lot, which helps keep things light even when it gets stressful.
My advice? Communicate clearly, respect each other's roles, and don't take everything too seriously.
GT: What key piece of advice would you offer a woman aiming to influence and lead in the group travel space as you have?
SB: Just be yourself. Don't try to overcompensate for what you think you're lacking—own it, improve it, and focus on what you do well. Also, be ready to work hard—this business never slows down. But the reward is worth it. Creating experiences that bring people joy and help them build lifelong memories is something truly special. If you lead with passion, purpose, and authenticity, you'll make a real impact.
GT: What are your goals for the future?
SB: In the short term, I'm focused on moving our business from New Jersey to Pennsylvania after 78 years, settling into a newly renovated space while keeping our core tour and charter businesses strong, as well as expanding College Break Bus to serve more schools and regions.
Long term, we're focused on growing our fleet and driver team, expanding the business—including showcasing our new Napaway coaches—strengthening our operations, and thoughtfully planning for a fourth generation of family ownership. At Starr, we're always looking ahead and building toward what's next.
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.
Barb Mock, President, Travel With Barb, 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.
Barb Mock holds CSTP certification, leads a CSTO-certified company, and is a two-time recipient of the Torch Award for Ethics. An active member of SYTA and a Trustee on the SYTA Youth Foundation Board, Mock is passionate about leadership, fostering teamwork, mentoring others, and creating meaningful opportunities through travel.
Her industry honors include being named one of the Top 10 Influential Women in Student Travel (2016), receiving the Groups Today Tenacity in Travel Award (2020), the Youth First Award (2024), and the Patriotic Employer Award from the Department of Defense. Most recently, she was named a 2025 Enterprising Woman of the Year.
Groups Today: What does it mean to you to be a woman leader in the group travel industry?
Barb Mock: To me, being a woman leader in the group travel industry means showing up with purpose, compassion, and confidence in a space where relationships and details matter. It's about leading with both head and heart to balance both strategy with empathy. I am proud to represent women in a field that shapes lives through experience, and I take seriously the responsibility of mentoring others, building and fostering relationships, and creating a culture where people feel seen, supported, and empowered to grow.
GT: How would you describe your approach to leadership?
BM: My leadership approach is grounded in relationships. I believe trust, respect, and genuine connection create the foundation for strong teams. I lead by investing in people by listening deeply, offering encouragement, and creating an environment where others feel supported and empowered. At the same time, I provide the structure and clarity needed for individuals and teams to thrive.
Leadership, to me, is not about having all the answers; it's about guiding others with purpose, modeling consistency, and helping people do meaningful work together.
GT: How do you use your influence to better the group travel industry?
BM: I hope my influence contributes to elevating our industry not through one voice alone, but through the mutual sharing of best practices, open collaboration, and a shared commitment to ethical, student-centered travel. By learning from and supporting one another, we strengthen the foundation of what we do. My goal is to be part of the ongoing work that moves our industry forward and leaves a lasting, positive impact for future generations.
GT: What are some of your favorite accomplishments so far?
BM: Some of my most meaningful accomplishments begin with the team I have had the privilege to build. Team TWB is truly second to none—their dedication, compassion, and commitment to serving others inspire me every day. Together, we have helped thousands of students experience transformative travel that builds confidence and broadens horizons.
While I'm honored to have received recognition for leadership and ethics, what matters most to me is the impact travel has on changing lives and the lasting relationships built along the way.
GT: What impact do you hope your work will continue to have on clients and peers?
BM: I hope my work continues to inspire confidence and possibility for both clients and peers. For clients, I want to make group travel feel accessible, manageable, and deeply meaningful and help educators and students create experiences that transform perspectives and build lifelong skills. For my peers, I aim to model leadership grounded in integrity and collaboration, encouraging a culture of support, innovation, and continuous growth. Ultimately, I want to leave a legacy of empowerment that fuels success and connection across the industry.
GT: What core values from your education career continue to guide your work today?
BM: The core values of patience, empathy, and dedication that shaped my education career continue to guide me every day. Teaching taught me the importance of meeting people where they are, listening deeply, and supporting growth in meaningful ways. My goal is to bring that same commitment to my work in group travel by prioritizing clear communication, thoughtful planning, and fostering positive experiences that empower both educators and students to thrive.
GT: What's your advice to women aiming to lead—and influence—in the niche of educational group travel?
BM: My advice is to stay open to learning. Be willing to ask for help, take classes, seek mentorship, and connect with other trusted business leaders. Listen to your team and empower them to share their ideas. As a leader, your job isn't to have all the answers but to lead the process of discovering them together. Growth comes from being curious, collaborative, and humble enough to learn from every situation.
GT: What are your goals for the future?
BM: Looking ahead, my goal is to continue building strong, trusted relationships—with educators, industry peers, and partners that make meaningful travel possible for more students. I want to expand access to life-changing experiences, especially for those who might not otherwise have the opportunity to travel.
I also want to keep supporting others in the industry however I can. That may be through mentoring, collaboration, or simply showing up and doing my best. At the core, it's about creating connections that elevate one another.
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.
