2025 Sailing Story Recap

2025 brought a variety of inspiring sailing stories from sailors in the Virgin Islands! Over the course of the year we captured the narratives of first-time sailors, new Go Sail employees, and students who had their lives changed by sailing! Here are a few of our favorite Virgin Islands sailing updates from our students and employees in 2025. 

Growing the Go Sail Crew

In 2025 we hired a new Operations Manager and captured the sailing stories of two of our new captains and one new first mate! 

• Claire DeDeckere had never even stepped foot on a sailboat before joining Go Sail as a first mate to Captain Jalil Jacallen— now she has not only found her sea legs but a lifelong passion!
• Tyler Evans embodies the spirit of curiosity and craft. A lifelong maker and explorer, Tyler’s journey into sailing — and his role as Operations Manager — blends passion for detail with a love of navigating new waters.
• Donna Acquaro joined the Go Sail team in 2025. She learned to sail in a bold, self-taught way long before formal instruction became common — an ode to perseverance and the breathtaking freedom of wind-powered boats.
• Bob LaBine has been a sailing instructor with Go Sail for a few years now but this is his first year teaching in the Virgin Islands! He brings decades of sailing to the table and his journey is a reminder that sailing is both a skill and a sanctuary.

The Newest Sailing Grads

Over the course of 2025, Go Sail graduated dozens of new American Sailing certified sailors! They can now take to international waters to bareboat charter! We are proud of the confidence all our new sailors gained over the course of their weeklong liveaboard sailing certification trips and highlighted a few new sailors in our sailing stories over the course of the year. We look forward to updating you in coming years about how they’ve used their newly acquired sailing skills:

• Rob Parke grew up with catamarans and later discovered the magic of sail-powered ones — proving that there’s always something new to learn, even in familiar waters.
• Christi Grindstaff, alongside her husband and son, answered the call of beautiful sailing stories shared by friends and embarked on her own family sailing journey, discovering how rewarding it can be to learn together.
• Nina & Jake took the leap into sailing together — for Jake, it was his first time aboard any sailboat, and Nina’s adventurous spirit pushed them both into an unforgettable experience filled with exploration and trust.

New Sailing Skills

We love when sailing students come back to Go Sail Virgin Islands to further hone their skills— or come to us with past sailing experience, now ready to become officially ASA certified! We chatted with a few students about how their sailing experience transformed for the better in 2025:

• Matt Krull found solace in sailing during the pandemic, trading COVID stress for the fresh air and challenges of the Caribbean. What started as a long-held wish became real wind in his sails as he honed his skills with confidence.
• William Whitacre found his way to sailing through a veteran’s yacht club. What began as a camaraderie-driven invitation opened up a world of wind, challenge, and community.
• Merrilee Hertlein first felt the pull of sails as a teenager and has since lived a life shaped by that early spark — proof that the sea often calls long before we answer.
• Nancy Hendrick shifted from loving kayaking to falling for sailing over a decade ago. Her story is one of evolving passions and discovering new horizons later in life.

The Path Forward

The sailors we followed in our 2025 Sailing Stories show us that the path to the sea isn’t always straightforward — and that’s the beauty of it. Some arrive with lifelong dreams, others stumble upon sailing by chance, and many return again and again as part of the Go Sail alumni community. Beyond learning skills, these journeys are about confidence, connection, and seeing what’s possible when you let the wind guide you. 

Here’s to more stories, more horizons, and even more sailors finding their sea legs in the coming year. May 2026 bring fresh winds, calm bays, and boundless inspiration to all who hear the call of the ocean!