Located on the eastern shore north of Pools Island, this is a true fresh water river.  Close to the head waters of this river lies Georgetown, MD.  Several marinas and restaurants are waiting for you if you venture up this beautiful river.  There are also several anchorage's available up the river.

This is a good trip to if you are looking to avoid the jelly fish common during the peak of summer.  They don't like the fresh water. 

Sassafras River

Spa Creek just off of the Severn River is home to Annapolis and the United States Naval Academy. This is truly one of the great boating destinations any where in the United States.  This historic maritime port is also the Capital of Maryland. As you enter the harbor you will see the dome of the Capitol Building proudly standing atop the hill overlooking the harbor and bay. You can anchor in the mouth of the harbor or up the creek past the Spa Creek Bridge. Moorings are also available harbor side and up the creek as well. They are first come first serve, and managed by the Annapolis harbor master. Recently they have added moorings for vessels over 50' they are marked with yellow.  Once you have secured your boat to the bottom you can dingy up ego alley to the city dingy dock or call the water taxi. Get your mooring ball # and they will pick you up at your boat. On land you can enjoy many dining options, shop till you drop, or visit the Naval Academy(its also a National Park, small fee to tour). This is a must visit if you are Cruising The Chesapeake. This is a great place to boat watch. You will see everything from Paddle boards to Mega Yachts. Something for everyone exists in this wonderful town!


This is a great anchorage for having a day in the sun. Deep water open space and beautiful views of both the shore line and the Miles River. This anchorage is located just in the Wye River. Follow the markers through the entrance to the river, make the first turn to starboard. just a few seconds around the point you will see Shaw Bay open up on your right.  Best protection is offered from a southerly wind. This is our go to spot for friends who don't often get a chance to be on the water.  Bring lunch  and enjoy a quiet spot for the day.

Shaw Bay

A very popular anchorage with good protection from most weather.  Holding is solid in a muddy bottom. Home to Great Oak Landing marina, the creek is an excellent overnight destination on the weekends.  Jelly Fish Joles beach bar is just inside the entrance.  This is a great place to people watch enjoy live music and summer libations.  There is room for lots of boats and deep water further south in the creek.  The entrance is well marked but vary narrow, use great caution if entering on an outgoing tide.  If you do arrive on an outdoing tide be sure you are heading south before you reach the entrance.  If the current hits you on your beam you will risk being swept on to the beach.

Fairly Creek

The Rhode is a popular spot south of Annapolis, this is a large area that get day boaters that land on a sinking island.  There is a sunken island at the top end of the river that is marked with with white danger bouys.  They are easy to miss and form a triangle.  We anchor facing the bluffs leaving the sunken island to our stern.  Be sure to set you anchor well .  This is a good anchorage with protection from the south and southwest. their are no speed limits so you might get some wake during the day. 


Located in Rock Hall Swan Creek provides excellent holding and good protection for most weather.  Beautiful views and easy access to shore.  Haven Harbor Marina has an access fee for use of facilities. You can make reservations at Osprey Point for dinner they have an upscale restaurant that is an easy dink ride.


While there are many excellent anchorages throughout the Chesapeake, these are our favorites. All are located throughout the middle and upper bay, as we keep the boat in the Annapolis area.



Cruising The Chesapeake