Private sailing charters, a short drive from Easton
No bridge, no bay traffic — just a straightforward Eastern Shore drive to a private, captained day on the Chesapeake.
The heart of the Eastern Shore, close to the water
Easton is home to many of the guests who sail with us. We're an easy drive up Route 213 — no bridge, no bay traffic — making us a convenient choice for a private day on the water without leaving the Eastern Shore.
Easton guests appreciate that a short trip up the road puts them at the dock, ready to head out onto open water.
- Capacity Private yacht for up to six guests
- Crew Dedicated professional captain
- Route Fully customizable — coves, towns, wineries
- Distance ~20–25 miles, about 35–40 minutes by road
Choose your trip
Full-day sail
Cruising, swimming, and a stop in Rock Hall, Annapolis, or St. Michaels.
Learn more →Overnight charter
Use Easton as a jumping-off point for a longer Bay adventure.
Learn more →Getting here
We depart from Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661. From Easton, most guests drive north on Route 213 and Route 20, arriving at the marina in about 35–40 minutes.
Ready to set sail from near Easton?
Your private Chesapeake Bay charter is just up the road. Let's design your trip.