Colleen Reilly: Sailing the Seas of Self-Discovery


In the tranquil coastal town of Biloxi, amidst the gentle lull of the Gulf of Mexico waves, there resides a woman whose life story is as captivating as the seas she has conquered. Colleen Reilly, a multi-faceted individual who wears the hats of a mother, grandmother, wife, and business owner, has an undying thirst for adventure that goes beyond the conventional roles life has thrust upon her.

“I know what everyone around me likes, wants, or needs,” Colleen reflects with a hint of contemplation. “But what about me? What about Colleen?”

This rhetorical question led Colleen on a transformative journey, one that would see her stepping out of her comfort zone, embracing the unpredictable, and discovering a new facet of herself. “I like to be needed,” she confesses, her eyes gleaming with a mix of excitement and introspection. “I want wine or chocolate, and I know I need self-care. But what do I really, really want? Besides, some peace and quiet every now and then?”

The answer to Colleen’s yearning for something more came in the form of an invitation—an invitation to be a volunteer crew member on a tall ship from Maine. The kind of ship that graced the pages of seafaring tales, adorned with towering masts and billowing sails, a far cry from the routine of her daily life. “Adventure usually finds me,” she laughs, her eyes dancing with memories. “And when it does, it’s with a capital A.”

It was an offer that demanded sacrifice—25 days without internet or a cell phone, navigating the Gulf of Mexico on a vessel that was more than just a boat; it was an oversized sailboat with a history etched in its wooden planks. Colleen’s decision to embark on this maritime escapade raised eyebrows among friends and family. Leaving her business and loved ones behind for the open sea seemed unfathomable.

“My adult children knew that I had finally lost my mind,” she chuckles, a glint of mischief in her eyes. “And my husband gently kept asking, ‘Do you really know what you’re getting into?'” Colleen, undeterred by skepticism, packed her sea bag with enthusiasm, ready to sail from Biloxi to Key West and beyond.

The first night at sea, however, was not the picturesque adventure she had envisioned. “It was like something out of a horror movie,” Colleen recalls, her expression momentarily somber. Thick fog enveloped the vessel, drenching her hair and clothing. The waves, relentless and unforgiving, tossed the ship in a chaotic dance, challenging even the most seasoned sailors.

“Seven hundred and ten miles across the Gulf of Mexico,” she states with a mix of pride and disbelief. Yet, amidst the turmoil, there were moments of pure magic. Colleen’s eyes light up as she describes the exhilaration of witnessing huge pods of dolphins leaping around the boat—a stark contrast to the tumultuous waves.

In the mornings, as the sun rose in the east and the moon set in the west, Colleen found herself in quiet amazement. The deep blue waters surrounding her became a canvas for nature’s artistry, a breathtaking sight that transcended the challenges she faced.

The professional crew, seasoned sailors with a wealth of knowledge, took Colleen under their wing. “They taught me how to do everything, from raising the sails to hauling up the anchor,” she says with a grin. “I even got to steer this massive tall ship.” The adventure became a crash course in seafaring, a chance to learn and apply skills beyond the realm of her everyday life.

“When I came home,” Colleen reflects, her eyes glistening with the residue of the sea breeze, “I returned to being a parent, a grandparent, a spouse. But I really, and I mean really, liked getting out of my comfort zone and discovering a new hobby.” The sea had become more than an expanse of water; it became a metaphor for self-discovery.

Colleen Reilly’s journey echoes a universal truth—that sometimes, to find oneself, one must navigate the uncharted waters of life. Her story is a testament to the resilience of the human spirit, a reminder that adventure, in all its unpredictability, has the power to unveil hidden facets of our identity. As Colleen continues to balance her roles as a mom, grandma, wife, and business owner, the echo of the sea remains—a constant reminder that the voyage of self-discovery is a journey that never truly ends.