Erin Stephenson

Grown on the Chesapeake Bay in Deale, MD, I find a sense of “home” within the maritime industry anywhere I go and am passionate about sharing the lifestyle with others, and about making dreams come true! I have spent most of my adult career as a sailing instructor and working within the waters sports industry in Florida, North Carolina, and the last 11 years in Hawaii. I have recently moved home with my family to immerse ourselves in the maritime history on the Chesapeake Bay, to teach my husband and daughter how to pick crabs, and to experience all 4 seasons again (eek). I am beyond stoked to work with the DiMillo’s Team to deliver an unrivaled hospitality and boating experience on the West Chesapeake. I have daydreamed about the Shady Oaks property since I was a child, and now I get to work with the team to make the vision come alive! Beyond boats, I love shelling, gardens, hiking, community events and volunteering, and a good yard game on a Sunday.

Erin joined DiMillo’s in 2025.