Waypoints Annapolis

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222 Severn Ave
Annapolis, MD 21403
The Finest Fleet on the Chesapeake Bay. We offer bareboat and fully crewed sailing charters. Take a boat for a day sail or spend a few weeks exploring all the Chesapeake Bay has to offer. We provide full itinerary planning and can recommend provisioning services. We take care of the details so you don't have to. Take a half or full-day cruise around the Annapolis area. The Chesapeake Bay is well-known as an outstanding waterway for sailboat cruising. Protected waters, great anchorages, gorgeous natural scenery, bountiful seafood, unique, historic towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. We can coordinate sailing charters at our home base on the Chesapeake Bay and anywhere in the world. Interested in learning to sail? Our certified instructors can take you on a Learn to Sail vacation and help you obtain ASA certifications. Let Waypoints Annapolis make your dream vacation a reality.

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1.01 reviews
Paul R.
6/9/2021

I chartered Recovery Room, a Jeanneau 51, over Memorial Day weekend 2021.  When I picked up the boat, there were a number of broken parts that were pointed out to me.  I was concerned that this...

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