Our Staff
Our team of Instructors and Instructors-In-Training ensures a safe and fun environment for every student. Each Instructor holds a US Sailing Level 1 Certificate and has CPR training. We focus on mentorship and skill-building to help your child thrive on the water.
Hannah Arey
Head Instructor & Racing Instructor
This is Hannah's third year as a Head Instructor and her sixth summer as an Instructor at Island Sail. She first learned to sail here at age 8, and Island Sail remained her only exposure to sailing until it sparked a passion that carried her into competitive racing in high school and college. Now in her thirteenth summer with the program, she brings that passion and experience to her role. Originally from South Portland, Hannah is a rising senior at American University, where she serves as Race Captain for the university's sailing team. In 2025, Hannah completed a trans-Atlantic voyage as part of the crew on a 40-foot sailboat sailing from Maine to Scotland!
Molly Frank
Head Instructor
Molly is spending her eleventh summer at Island Sail and her third on the Instructor team. This is her first year as one of our Head Instructors. Originally from Saratoga Springs, New York, Molly just graduated from Northfield Mount Hermon, a boarding school in Massachusetts, and will be attending Bates College in the fall. When she's not sailing, Molly rows and plays hockey. Her steady presence makes her a valued member of the Island Sail staff.
Henry Nero
Instructor
Henry just turned 19 and has been sailing with Island Sail since he was 7. This is his sixth year on staff and third year as an Instructor. Henry's family recently moved from Connecticut to Maine, he graduated from Millbrook, a boarding school in upstate New York, where he played lacrosse, and he will be attending Bates College in the fall. Henry has spent every summer of his life on Vinalhaven and is looking forward to an another amazing summer on the island. Henry brings an abundance of energy and good cheer to Island Sail!
Sean Walton
Instructor
Sean is 18 years old and comes to Island Sail all the way from Round Rock, Texas. This is his eleventh summer with the program and his third as an Instructor. Sean will be attending the University of Alabama in the fall. A familiar and friendly face on the dock, Sean is known for never hesitating to jump into the ocean with new sailors for the swim test—his encouragement helps everyone feel at ease. Island Sail has been a home away from home for Sean for over a decade, and he's excited to pass along this skills and traditions he learned here to the next generation of sailors.
Ibis Bird
Instructor
Now in her tenth summer at Island Sail, Ibis brings a lifetime of coastal sailing experience to the team. A native of Belfast Maine, she has spent every summer on Vinalhaven and has cruised the Maine coat with her family since she was young. This is her third year as an Instructor. Ibis is 17, swims competitively, plays soccer, and will spend her upcoming senior year of high school studying in Argentina. Calm, capable, and confident, Ibis is a natural on the water.
Isaac Arey
Instructor
A rising Senior at South Portland High School, Isaac is enjoying his second year as an Instructor after sailing with us since he was 7 years old. He's the 2021 Island Sail Sailor of the Year, and he's been a dedicated part of our community. Isaac is 16, and when he's not sailing, he's playing soccer, running track, fishing, or out exploring in a motorboat. He brings energy, focus, and fun to every day on the water.
Harry Young
Instructor
Harry is 16 years old and has been sailing with Island Sail for the past 8 years. He is a rising senior at Richard Montgomery High School in Rockville, Maryland, where he plays in both the marching band and jazz band. Outside of sailing, he enjoys gardening and baking bread, and he even used to sell his homemade bread at the Vinalhaven Flea Market. This summer marks his first year as an Instructor, and he is excited to share his love of sailing, get to know this season's sailors, and help them have a fun and memorable time on the water.
Teddy Helgerson
Racing Instructor
Teddy is 19 years old and from Philadelphia. A graduate of Germantown Friends School, he just finished his first year at Swarthmore College where he studies environmental science and economics and plays baseball for the College. He speaks English and Spanish, plays the violin, and was the lead singer for the boy band Trash in the Attic. Teddy began sailing on his great grandfather's dinghy on the Chesapeake Bay when he was five. He began sailing at Island Sail when he was 7 and was awarded Sailor of the Year in 2018. Teddy's favorite Island Sail memory is capsizing 18 times on a windless day in Sands Cove. He brings experience, focus, and a sense of adventure to Island sail.
