On February 2, 2026, six Hurricane Island Outward Bound School instructors set sail on a 22-day unsupported wilderness expedition through the Florida Keys and Everglades aboard a 30-ft. sharpie. This is the first Miles Turner Expedition, and right now it’s unfolding the way long trips do—one watch, one decision, one day at a time.

They’re traveling aboard Eliza Sue, generously loaned for the expedition by longtime HIOBS supporter John Cushing (thank you, John!), and for the next three weeks, this boat will be their home. It will serve as a place to sleep, cook, navigate, problem-solve, and share the everyday moments that make extended expeditions so formative.

About the Expedition
This expedition is being done in memory of Miles Turner, a friend and fellow instructor who passed away last year and who felt most alive on long, committing wilderness expeditions. Miles loved the depth that comes from being out long enough to settle in—the way time stretches, the way a group evolves, and the way learning happens quietly through lived experience. This journey carries that spirit forward.

It also marks the first time the Miles Turner Expedition Fund has been put to use. Created by HIOBS in Miles’s memory, the fund exists to support active HIOBS field staff and program leadership in pursuing ambitious, extended wilderness expeditions—the kind of trips that don’t fit neatly into a course schedule but shape instructors in lasting ways. This crew’s 22-day sailing adventure was selected as the fund’s first expedition, and it feels like a fitting beginning.

An area that Miles instructed in on multiple semester courses, the waters of the Keys and Everglades are dynamic: shallow flats, winding mangrove channels, shifting tides, and long days where progress depends on patience and teamwork. Sailing unsupported means every decision is theirs—from navigation and weather calls to pacing, rest, and showing up for one another when fatigue sets in.

About the Crew

The six people sharing this experience are all HIOBS instructors, each bringing their own experiences, relationship to sailing, and connection to Miles:

• Gray George – Gray first met Miles in the summer of 2024 while working their first HIOBS course. It was a challenging course, yet through it all, Miles remained compassionate, grounded, and full of love. Gray carries many of his lessons and instructor practices forward on every expedition.
• Arran Denning – Originally from the UK, this past summer was Arran’s first season teaching sailing with HIOBS. Though Arran never met Miles, his impact is felt through the stories shared by those who knew him, serving as an inspiration to be kind, curious, and support others in the outdoors.
• Ben Lidoski – Ben instructs both sailing and backpacking courses with HIOBS. Prior to his first season in 2024, Ben crossed paths with Miles during a Wilderness First Responder course, where Miles always found a way to make people smile. He is honored to sail somewhere he knows Miles loved.
• Sofia Fea-Ruiz – Sofia has spent the past two summers sailing with HIOBS and remembers Miles’s passion for outdoor education and the curiosity and patience he approached students with—qualities they continue to carry into every expedition.
• Roo Abdel-Al – Roo taught sailing with HIOBS last season, and through stories shared about Miles during that time, it has inspired them to push beyond what’s comfortable and become a better educator.
• Andrew Phelan – Andrew has worked in logistics and as a sailing instructor for HIOBS for the past few years. Andrew sees Miles as someone to aspire to be like—not just as an outdoor educator, but as a person and a friend—and carries that inspiration into this expedition.