Chesapeake Sailing Charters

Sailing Grounds

Suitable for Weekend Cruise Leaving from Herrington Harbour North


Interested in history? Then visit a historic village - the communities of St. Michaels, Oxford and Solomon's Island are easily within your reach. Stay at local marinas or find a secluded anchorage. Enjoy nearby restaurants or eat aboard, its your choice. 

We will be happy to help you plan an itinerary if you would like some suggestions and each boat has helpful information aboard specially prepared for you.


You may also visit the Herrington Harbour Marina website to learn more about are restaurants, overnight accommodations, beaches, and services.




Your relaxing sailing vacation will start as soon as you leave the Washington beltway. You will travel through some unspoiled Maryland countryside and arrive at the Herrington Harbor Marina refreshed and ready to begin your trip, not a bundle of nerves from Washington area traffic.


If city life is your desire, let Annapolis become your destination, not your starting point. Sail up to Annapolis and pick up a mooring buoy in Annapolis harbor on a first come first served basis, or anchor in the harbor or nearby Whitehall Bay. Then enjoy all that Annapolis has to offer after an enjoyable sail.