Captained and Bareboat Charters in Annapolis, Maryland

The Chesapeake Bay is among the world’s top cruising and sailing destinations. From quiet, pristine anchorages, to historic seaside villages, to the busy ports of Baltimore and Annapolis, the Bay offers something for everyone.

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

For Reservations or More Information, Contact Us


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Ships docked in and Annapolis harbor