Sailing charter Cruising Destinations

Example Itineraries and places to explore.

 Destinations to Visit and Explore

Destinations to Visit and Explore

Welcome Aboard!  The Chesapeake Bay is the largest bay and estuary in the United States as well as one of the premiere sailing destinations in the world.  It can be divided regionally into north and south. In the northern region, the Chesapeake Bay is home to the United States Naval Academy, which is located on the western shore in Annapolis, Maryland.   Baltimore is almost directly across the bay from Rock Hall as is the Magothy River.  A sail up the Chester River bring you to historic Chestertown.   To the north is Chesapeake City, located on the famous Chespeake and Delaware canal. The "C&D", as the canal is commonly called by mariners, connects the Delaware River to the Chesapeake Bay;  and is considered the northern entrance to the bay.  Multiple anchorages, such as Still Pond, Fairlee Creek and Worton Creek are all perfect for a day sail,  a multi-day trip , or a week of cruising and gunk-holing.   Seeing the wildlife and gorgeous sunsets will take your breath away.  Sailing south along the eastern shore you can explore magical and historical towns such as St. Michaels, Oxford, Cambridge, and Crisfield.  In the southern region of the bay, consider a cruise to Solomons Island at the mouth of the Patuxent River or other areas such as Deal Island or Nanticoke.  In this part of the Chesapeake Bay we are able to easily access the historical waterways of the Potomac, the Rappahannock and the York rivers. Sail across the bay from the southern western shore to visit Cape Charles and Kiptopeke or continue sailing southwest to the James River, Hampton, Newport News and Norfolk. As we sail south, you may even get to see some dolphins.  If you so desire, we can even sail you to view the Chesapeake Bay Bridge and Tunnel until we reach the Atlantic Ocean!  

Any itinerary you choose will immerse your body and soul with the sights, sounds, smells and tastes that cruising the Chesapeake Bay has to offer. 

Example Itineraries

  • Day Sailing to the Magothy River, where we can anchor for a BBQ lunch; then return on a leisurely cruise back to Rock Hall. After your sail you can go crack crabs at Watermans Crab House or enjoy an amazing meal at Osprey Point Inn and Marina.

  • Enjoy a sunset sail and enjoy the exquisite colors reflecting off the water during the "Golden Hour".

  • Night Sailing on a full moon cruise or without the moon gazing at the stars.

  • How about a weekend cruise including a visit to Annapolis where you can enjoy a nice dinner ashore, maybe at a classic crab house like Jimmy Cantlers Riverside Inn. Spend the night on anchor and set sail the following day to one of the thousands of gorgeous creeks or bays where you can be surrounded by nature. Alternatively, head for the eastern shore to visit St. Michaels or other small towns. Other possible destinations include Baltimore, the Magothy River, Still Pond as well as other anchorages such as the Rhode or West Rivers.

  • Custom multi-day and week-long adventures could include a trip to Oxford, Cambridge, Solomons Island and stops along the lower Potomac River. No matter what your sailing needs might be, consider Shardana Sailing Charters as your number one source for Chesapeake Bay sailing.

 Ready to sign on? Book your adventure now.