Meet the Crew!

Gray George
Hey, I’m Gray! I’ve been sailing for a few years now, primarily in midcoast Maine, with a few side expeditions in the Florida Keys and the Bahamas. I am also in the process of applying for my USCG Captain’s license, and hope to be sailing on it this summer with Hurricane Island Outward Bound School. I’ve always been an ocean lover, and when I’m not working, I’m surfing, traveling, or spending time with my favorite people. I first met Miles in the summer of 2024, and worked my first course ever as an instructor with him. It was an immensely challenging course with our group of students, and through it all, Miles remained compassionate, grounded, and full of love. I learned so much from him in that short amount of time, and carry on some of his instructor practices to this day. I am immensely grateful to be sailing in his honor this winter, and to continue his legacy through fundraising for places and causes he truly believed in.

Arran Denning
My name is Arran. This summer was my first as a sailing instructor at HIOBS. I’m from the UK and I’ve been mucking around on boats since I was teeny tiny. I never got to meet Miles but I am learning more and more about him from our community as the months go on. He meant so much to so many people and I am honoured to be sailing for him, for what we have lost and for what he loved. His memory strengthens me to be kind and curious and support others in the outdoors. When I cook a big community meal or have a long conversation with a student I often think of what I’ve been told about him and what he has taught me through others.

Ben Lidoski
Hi, I’m Ben. I’m a Sailing and a Backpacking & Canoeing course instructor at the Hurricane Island Outward Bound School. I’ve been on a handful of sailing expeditions, all of them with the school – originally as a student in the Bahamas, and now as an instructor in midcoast Maine. I first met Miles in 2024 during a Wilderness First Responder course prior to my first season at HIOBS. He was always cracking jokes and finding ways to make the people around him smile. It’s an honor to be able to sail somewhere I know Miles loved.

Sofia Fea-Ruiz
Hi, I’m Sofia! I’ve spent the past two summers sailing as an instructor for the Hurricane Island Outward Bound School, where I met Miles in 2024. His passion for outdoor education as a way to inspire growth and self-awareness shone in every conversation I had with him. When I find myself in difficult situations, I remember the curiosity and patience that he approached his students with. I’m excited and grateful for this opportunity to sail and fundraise in his honor, surrounded by other inspiring outdoor educators and in a place that has a deep history in the HIOBS community. I’m looking forward to the marine wildlife we will see!

Roo Abdel-Al
Hi, I’m Roo! I’ve spent the last summer sailing with the Hurricane Island Outward Bound School. Learning about Miles throughout the season inspired me to push myself beyond what is comfortable which in turn, has made me a better educator. His harmonica, the stories of his cooking and the anecdotes of how he taught will always be carried with me. It is a privilege to sail with those who share his values and who are committed in disseminating those values in his honor.

Andrew Phelan
Hi friends! My names Andrew, I’ve been working for HIOBS for a few years now in logistics and sailing instructing. I love to climb, hike, sail, paddle or just sit underneath a nice tree. I’m currently refinishing a boat in the off season in cold wet New Jersey excited to rejoice in the Florida weather. Miles is someone that I aspire to be like, not just within the scope of being a great outdoor educator but also as a person and friend. I also built this website, so if there’s an issue let me know!