Stacey Ray of Sisterhood Travels Empowering Women 45+ with Life-Changing Solo Travel Experiences

Please share a brief introduction about yourself and your business

I am the founder and driving force behind Sisterhood Travels, a pioneering tour operator dedicated to empowering women through curated, life-changing travel experiences. With a personal travel history spanning more than 80 countries, my journey began alongside my late husband, Mike, whose adventurous spirit and our shared explorations shaped my belief in the profound, transformative power of travel. 

After experiencing the loss of my husband, I turned my grief into purpose, creating Sisterhood Travels as a safe, supportive space for women to explore the world—and themselves. Today, Sisterhood Travels is a thriving community where travel is more than an escape; it’s a journey of self-discovery, connection, and empowerment. 

Our thoughtfully designed trips redefine solo female travel, offering unique and enriching experiences that foster independence, confidence, and meaningful friendships among women of all backgrounds. My mission is to inspire women to step beyond their comfort zones, embrace new horizons, and discover the transformative magic that travel holds.

Who are your customers?

Our customers are women aged 45+

What was your background prior to starting your own business?

I spent 30 years in healthcare. First, as a critical care respiratory therapist. Then, I became the first non-nurse, non-social worker to ever be hired by UNC Hospitals in Chapel Hill as a Case Manager where I served for almost a decade with cardiology and heart failure patients. I went on to receive my Masters in Public Health and was a Certified Case Manager and a Certified Asthma Educator. Travel was a bit of a side hustle beginning in 2014 where I specialized in group travel for both leisure groups and MICE groups.

What made you take the leap to start your own business?

When my husband died, I felt lost and didn't know how I would continue traveling because I had no one to travel with anymore. I realized that if I felt that way, other women must feel the same way. This was how Sisterhood Travels was born.

Did you always know you wanted to be an entrepreneur?

Yes but the older I got the more I kept pushing it to the side. Until I was 60 years old and realized that I had an idea that could help not only me, but many other women as well.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

Honestly, I was winging it - it was 100% organic on Facebook and word of mouth. I started a fairly primitive website that I designed myself and I opened a private group on Facebook. About 250 women (friends and family who I think felt sorry for me) joined the group. Now, we have 44,000 women in that group with a very high engagement record and an email list of almost 30,000 women. The fact that we've seen this growth since 2021 with zero paid advertising has been remarkable and beyond my wildest dreams.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

Working with family members and friends. I've learned that if you can avoid it - it's a much cleaner situation. Working with family is beyond difficult and I find that I am a referee and spend much of time dealing with personality conflicts. Hiring friends is an extremely tricky business, especially when "friends" feel they are entitled to special privileges and ultimately, I've been betrayed by those who I thought were my friends.

What accomplishment are the most proud of to date in your business?

The magic of seeing our women (we call them "Sisters") transform their lives through travel. We watch women every day who have never flown on an airplane find the courage to fly across the world to meet women they don't know. The women become immediate friends - they are kind, supportive, and engaged with each other and they learn that they are not alone. Women who travel with Sisterhood Travels are building confidence, learning new life's skills, and refusing to become invisible just because they are older. It makes my heart sing to watch the resilience and bravery of our Sisters.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

Yes! I've just launched a brand new podcast, Life. Reimagined. with Stacey Ray which is both video and audio. We are booking and recording the most incredible women who sharing their deeply personal stories of resilience, and how they truly are turning life's detours into new destinations.

What's next for your business? What can we expect to see over the next few years?

We will continue to be trailblazers in the solo travel for women genre. We are always setting the bar higher. We will be introducing a very exciting new program in January 2026 to build an even stronger  community for our Sisters. I am designing more and more trips that are off-the-beaten track and offer incredible cultural exchange opportunities because I believe that we should leave more than we take when visit these destinations. What this means is that we have a global Sisterhood that we will be getting to know even more intimately. We are creating a movement for women to be invincible, not invisible.

What is your top productivity tip?

I wake up every day to begin work at 4am. I accomplish more between 4am - 9am than most people do in an entire day (or two). I find that being able to work without the interruptions of the business day, allow me to be far more productive.

On the flip side, how do you avoid burnout?

This can be challenging as a founder and as someone who is responsible for 100% of the risks of being in business. I have had to change my mindset and realize that I am of no value to the business or my team if I am so burned out I can't function. So, I listen to podcasts (true crime) and I use a coloring app on my phone to allow myself to remove all thoughts of work - even if it's just for 30 minutes or an hour at a time.

What is your approach to work-life balance / integration?

As someone whose mission it is to empower women to engage in self-care, I find the best form of self-care is a "Me-Moon" - a trip to anywhere (even if its the hotel 2 blocks from your house where you snuggle up with a book) all by yourself is the antidote for just about anything. It's hard work to commit to a Me-Moon but it is absolutely the best way to find that work-life balance because you must separate yourself from the demands that everyone is placing on you.

What is one thing you wish you had known when you started your Entreprenista journey?

That negotiating team conflicts is the hardest part of of my job.

My best hiring tip is this: You can generally teach anyone skills but you cannot teach character, integrity, or initiative. If a potential employee does not have these qualities, it doesn't matter how skilled or experienced they are - you'll find they will never be a good fit for your business.

If you've raised capital for your business already, what are some of your best tips or lessons learned?

I funded my business 100% with my own money and my business has always been 100% debt-free - something I am enormously proud of.

What's the one app on your phone you absolutely cannot live without and why?

Color Planet - its my coloring app - my therapy - my remedy for burnout.

What is your favorite business tool or solution and why?

Monday.com - it has become the lifeline of our business between the CRM capabilities, project management, reporting, integrations, automations, and reporting - it's a must-have for every business.

What advice do you have for aspiring Entreprenistas?

It's the same advice I give to our travelers: What is the difference between an adventure and an ordeal? ATTITUDE! You can have a melt-down, you can give up, you can quit - OR...you can say I've got this and find your way and reach your goals. Nothing is ever as we plan - life is full of detours, especially when you have dreams and aspirations. Your success will depend on how you cope with those detours.

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