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About Us


Five O' Clock Charters believes that the wonders of the Chesapeake Bay and the beauty of the Annapolis area are worth experiencing from the water. We are a skilled captain and crew with a comfortable and sturdy craft, and we would love nothing more than to enable as many people as possible to enjoy the Bay as we do.

We believe in the importance of relaxation, and have a deep appreciation for sailing. We believe sailing has a special ability to help people de-stress and adds value to the Annapolis experience. Sailing is one those activities in which you can become totally immersed, and for that reason it makes the perfect getaway. Whether you are trimming sails, keeping the boat on course, feeling the power of the wind driving the boat through the water, or just basking in the beauty and solitude of being on the water, one can easily disconnect for a while on a sailboat.   

The Captain

Annapolis native Michael Jewell is a USCG licensed Captain (50-Ton Master) with 20 years of both racing and cruising experience, much of it gained right here in the Annapolis area of the Chesapeake Bay. Offshore experiences include Annapolis to Newport, Annapolis to Bermuda, as well as several charter sails in the British Virgin Islands.  

The Boat

Five O' Clock is a 1987 O'Day 40-foot craft with amenities such as a covered cockpit, cockpit cushions, and open decks. Below decks you will find a fully equipped main salon (seating area), galley (kitchen), and fully enclosed head (toilet). She is a sloop rig which consists of a mainsail and jib with a 40 HP inboard diesel engine.