Chesapeake Bay Cruise Itineraries for Sailors

Cruise the Chesapeake!

Whether it's a weekend escape or a  or a two-week getaway, Upper Bay or Southern Bay, we've got some ideas to share about where to sail on the Chesapeake Bay. From urban slips to anchorages in quiet coves, you'll find reasons enough to cruise all season!

cruise to Eagle Cove
Eagle Cove, off the Magothy River, is a favorite of many cruisers because of the nice anchorage area and scenic horse farm on shore. Photo by Susan Theuns

Three-Day Middle Bay Cruise

~Submitted by Kathleen Kryza

Day 1 Anchor at Eagle Cove on the Magothy River

Day 2 Baltimore; Harbor East Marina, walk/cab to a ball game

Day 3 Rock Hall, MD; with a slip at either Haven Harbour North or South, borrow bicycles and ride to town, have dinner at the newly renovated Waterman’s Restaurant

Weeklong Northern Bay Cruise

~Submitted by Sue Mikulski

Option 1

Day 1 Eagles Cove on the Magothy

Day 2 Cross the Bay to the Eastern Shore to Worton Creek, anchor out

Days 3-4 Sassafras River; anchor out one night and spend one night at one of the marinas in Georgetown

Day 5 Return back to the Bay and to Fairlee Creek; anchor out

Day 6 Rock Hall; anchor or reserve a marina slip

Option 2

Day 1 Eagles Cove on the Magothy

Day 2 Bodkin Creek, just south of the mouth of the Patapsco River

Day 3 Havre de Grace

Day 4 Worton Creek

Day 5 Fairlee Creek

Day 6 Rock Hall

Sailboat cruise raftup
America's Boating Club Wilmington members rafted their boats in Harness Creek, June 2023. Photo by Terry Butler

Weeklong Middle Bay Cruise

~submitted by Carol Hanson, America’s Boating Club Wilmington

Day 1 North Point Marina in Rock Hall, MD

Day 2 Rhode River, south of Annapolis; anchor out

Day 3 Herrington Harbour Marina

Day 4 Little Choptank, Hudson Creek; anchor out

Day 5 Oxford, MD; slips or anchor out

Day 6 Lay Day in Oxford; tour Chesapeake Bay Maritime Museum and visit town

Day 7 Dunn Cove off Harris Creek in the Choptank, anchor out

Day 8 Annapolis; Port Annapolis Marina 

cruise to Mill Creek
Beautiful sunsets are one of the many reasons to cruise the Chesapeake Bay. Mill Creek, off the Great Wicomico River. Photo by Susan Theuns

12-Day Southern Bay Cruise

~Submitted by Susan Theuns

Day 1 Herrington Harbor South

Day 2 St. Leonard’s Creek off the Patuxent River; anchor out—high shores, deep water; dinner at Vera’s in Lusby, MD                                                  

Day 3 Crisfield, MD; Sommers Cove Marina

Day 4 Lay Day in historic Crisfield                                                 

Day 5 Fleet’s Bay, south of the Potomac, north of the mouth of the Rapahannock; anchor out

Day 6 Cape Charles, VA; Town Harbor Marina

Day 7 Lay Day in Cape Charles                                                                    

Day 8 Gloucester Point, VA; slips at York River Yacht Haven on Sarah Creek

Day 9 Deltaville, VA; anchor out or grab a slip at Fishing Bay Marina   

Day10 Great Wicomico River; anchor out in Mill Creek

Day 11 Smith Creek off the Potomac; anchor out

Day 12 Solomons Island; Zahniser’s Safe Harbor Marina; dine at La Vela

Read more great cruising articles.

More Middle Bay itineraries