Head Sailing Instructor 

This is Hannah’s second year as Head Instructor and her fifth summer as an Instructor at Island Sail. Hannah just completed a trans-Atlantic journey as crew on a 40-foot sailboat sailing from Maine to Scotland! 

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 twelfth summer with the program, she brings that passion and experience to her role. Originally from South Portland, Hannah is a rising junior at American University, where she serves as Race Captain for the university’s sailing team. Before college, she raced with the Southern Maine High School Sailing Team from 8th through 12th grades and was the team captain for two of those years.

Sailing Instructors

James Nagel

James is in his tenth year at Island Sail and his fourth summer as a member of the staff. Originally from Cleveland, Ohio, James grew up sailing at Island Sail and brings years of experience, energy, and enthusiasm to the program.  He is currently a student at Syracuse University, where he is majoring in Sport Analytics. Outside the classroom, James is an active member of the sailing team, as well as the club ski racing and lacrosse teams.  Clearly, James has a love of all things active—on land and on the water.

Teddy Helgerson - Captain

Teddy is 18-years-old and from Philadelphia, where he graduated from Germantown Friends School in June. In the fall, he will attend Swarthmore College where he plans to study environmental science and economics and play baseball. He speaks English and Spanish, plays the violin, and is the lead singer for the boy band "Trash 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 seven and was awarded Sailor of the Year in 2018. He has taken racing classes at North Haven’s Casino and spent a Covid summer taking privates and learning to race lasers. With his family, he continues to sail on Vinalhaven's Seal Bay, on the Delaware River, and in the Chesapeake.

Teddy’s Favorite Island Sail memory is capsizing 18 times on a windless day in Sands Cove. Teddy will be the Captain of the Intermediate class. He brings his experience, focus, and sense of adventure to Island Sail!

Henry Nero, Captain  

Henry just turned 18 and has been sailing with Island Sail since he was 7. This is his fifth year on staff and second year as an instructor. Henry will be the  Captain of the Beginner sailing class this summer. Henry’s family just moved from Connecticut to Maine, and he goes to boarding school in Upstate New York at a school called Millbrook, where he plays lacrosse. Henry has been coming out to Vinalhaven his entire life and is looking forward to another amazing summer. Henry brings an abundance of energy and good cheer to Island Sail!

Ibis Bird

Now in her ninth summer at Island Sail, Ibis brings a lifetime of coastal sailing experience to the team. She has spent every summer on Vinalhaven and has cruised the Maine coast with her family since she was young.  Ibis is 16 and lives in Belfast. This is her second year as an instructor. In the off-season, she’s a high school junior who swims competitively and plays soccer. Calm, capable, and confident, Ibis is a natural on the water.

Molly Frank

Molly is spending her tenth summer at Island Sail and her second on the instructor team. Originally from Saratoga Springs, New York, she is a rising senior at Northfield Mount Hermon, a boarding school in western Massachusetts. When she’s not sailing, Molly rows and plays hockey—and when she’s home, you’ll find her back on the water. Her steady presence makes her a valued member of the Island Sail staff.

Sean Walton

Sean is 17 years old and comes to Island Sail all the way from Round Rock, Texas. This is his tenth summer with the program and his second as an instructor.  A familiar and friendly face on the dock, Sean is known for never hesitating to jump into the ocean with new sailors for their 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 the skills and traditions he learned here to the next generation of sailors.

Isaac Arey

Isaac is Island Sail’s newest instructor, but he’s no stranger to our waters—he’s been sailing here since he was 7 years old. In 2021, he was named Island Sail’s Sailor of the Year, and he’s been a dedicated part of our community ever since.  Isaac is 15 and from South Portland. 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.

2025 Instructors in Training

Emmy, IIT

Dylan, IIT

Harry, IIT

Mia, IIT

Finn, IIT