Why Choose Chesapeake Sailing Charters?

Because our charters are designed with your needs as charterer foremost in our mind. You want a carefree experience with the least amount of interference from your charter company and without add-ons and restrictions. Our weekend charters begin at 5:00 PM on Friday. After a quick checkout, you are free to leave the dock or stay as you desire. Head for your anchorage, go for a sunset cruise and return to the dock or stay at the dock for dinner, cocktails or visit the restaurants in town. There are no extra sleep aboard fees for Friday night or after your cruise on Sunday night. Also every charter includes a Walker Bay hard dinghy at no extra charge.

We are located at Herrington Harbour North, one of the most beautiful and environmentally conscious marinas on the East Coast. 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 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.

If you would like to visit a historic village, 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.