Choose Your Charter!
- Most Popular!
Escape the crowds and enjoy a private day sail along the scenic coastline and hidden coves. Perfect for couples, families, or small groups, our sailing charters offer a relaxed and personalized experience on the water, complete with breathtaking views and expert local guidance.
- All Ages
- 4 & 8 Hours
About Shore & Island Sailing Charters
We are a boutique sailing charter company based between the historic seaside towns of Oxford and St. Michaels, Maryland, cruising the serene waters of the Tred Avon and Miles Rivers and out into the storied Chesapeake Bay.
Inspired by the timeless romance of Chesapeake sailing, our company was created for guests who want more than just a boat ride—they want an experience. Sailing the Chesapeake on a catamaran is a blend of smooth speed, wide-open comfort and endless coastal scenery
With twin hulls skimming the water, the boat stays level and stable while the breeze fills the sails. We blend classic maritime heritage with the comfort of a private, personalized charter.
Here, a sail can be as serene—or as spirited—as you want it to be. Sit back and savor the quiet rhythm of the water or feel the thrill as the sails fill and the bow slices forward.