Why settle for ordinary when you can make your retirement epic? This is your
time to embrace adventure, push boundaries, and live your boldest dreams.
For Deborah Hammett, that dream didn’t reveal itself until after she retired from teaching
on Martha’s Vineyard. Only then did she set her sights on an audacious new
chapter—becoming a sailor. With her sharp wit and seasoned teaching skills, she not only
masters the art of sailing, but guides and inspires fellow adventurers of all ages.
Join Deborah on her remarkable solo voyage from New England to the Southern Bahamas
and back. Along the way, she conquers fears, navigates unexpected challenges, and
reexamines long-held beliefs. Her journey is more than a sailing expedition—it’s a
testament to the power of reinvention and the limitless possibilities that await when you
dare to chase the horizon.
Deborah Hammett grew up in Katonah, NY, and received her bachelor’s degree in elementary education at Western Connecticut State University. She started teaching in Oak Bluffs, Massachusetts, in 1986. While on maternity leave, she commuted off-island for graduate school and received her MEd. in school leadership at Salem State University. She taught at several grade levels and was a school principal before she retired and learned to sail. She has two grown daughters, Rilla and Emily. She now sails between the Bahamas and Martha’s Vineyard, living aboard her boat, Mavia.