Ego Alley Annapolis Sailing

Captained and Bareboat Charters in Annapolis, Maryland

The Chesapeake Bay is among the world’s top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside towns like St. Michaels and Oxford, to the vibrant ports of Baltimore and Annapolis, the Chesapeake Bay offers something for everyone.

Our docks in historic Eastport overlook the celebrated city of Annapolis and the Naval Academy. Take a short stroll or dinghy ride into town and enjoy the quaint shops and world-class restaurants before heading out on your Chesapeake Bay adventure.

Charter with Waypoints® Annapolis to Experience:


  • Daily, Weekend, and Week-Long Charters 
  • Skippered, Bareboat, and ASA Certification Charters 
  • New Luxuriously Appointed Fountaine Pajot Sailing and Motor Catamarans, Dufour Sailing Monohulls, Jeanneau Sailing Monohulls, and Jeanneau Powerboats
  • Yachts Equipped with Air-Conditioning and Generators 
  • Provisioning and Personal Concierge Services

Contact an Annapolis Charter Specialist Today


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Ships docked in and Annapolis harbor