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
An Insider’s Viewpoint
“How would we describe the perfect cruise from Annapolis to St Michaels? Talk to Susan and Traci at Waypoints and hire Mike to be your captain and chef extraordinaire!
Booking was easy and Dark Star was the perfect venue for our sail on the Chesapeake. We were blessed with beautiful weather and we never lacked in getting the details we needed quickly when we asked questions and made requests.
We launched the boat from their very accessible location on the Eastport side of Spa Creek. They helped us navigate parking and Waypoints had people help us with our luggage. We can’t say enough good things about our experience. They exceeded our expectations!”
Julie M.
An Insider’s Viewpoint
“If you are looking for a Five-Star full-service charter experience and marina, look no further than Waypoints Annapolis. The boat was in mint condition and the service at the Marina was exceptional. Annapolis is a beautiful historic city with great restaurants and a fun nightlife for those who want to spend an evening onshore.”
Mike
An Insider’s Viewpoint
“This may be the best charter company I have ever used. Fantastic customer service, wonderful, perfectly maintained boats, price competitive, perfect location right on the Severn next to Chart House, boat choice from small to large.”
Sandy
An Insider’s Viewpoint
“Phenomenal company, team, and experience, from start to finish! Waypoints Annapolis offers the finest yachts for charter and boat-as-business opportunity we’ve ever seen!”
Karen
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