Best results for Sailing in St. Michaels, MD

Sail the Chesapeake on a 1935 ketch with the option to join the crew

Sail the Miles River with room to relax aboard Epiphany

Sail Chesapeake Bay at sunset with champagne and light bites

Celebrate the bride or groom aboard a historic private sailboat

Private Chesapeake Bay sailing aboard a 1935 ketch

Sail the Miles River aboard a historic 1935 ketch

Sail a historic ketch at sunset with champagne and Chesapeake Bay views

Private catamaran sailing with harbor views and Miles River breezes

Sail the Miles River aboard a spacious catamaran

Harbor views and wind-powered sailing on the Miles River

Savor rotating craft beer tastings aboard the historic Lady Patty

Build Practical Sailing Skills With Private, Hands-On Instruction

Take the Helm and Learn Hands-On Sailing Skills