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Points of Interest

Bloody Point Light on the Chesapeake Bay

A charter sail is a great way to experience more of what makes Annapolis so special: 19th-century lighthouses still in operation, the magnificent Chesapeake Bay Bridge, historic buildings nestled in small coves, and one of the most gorgeous cityscapes you will ever see. Five O'Clock Charters provides the best seat in the house for observing ospreys and their chicks nested on buoys, sailboat races in action, quaint harbors, and so much more. You could spend a year sailing the Chesapeake Bay and still not see all that it has to offer. Let us know what you want to see, and we will plan a route that is sure to please you.

Highlights on the Bay

Kayaking in Harness Creek

Harness Creek is a calm and scenic place to drop anchor and have a swim, do some paddleboarding, or explore the waters by kayak.

A steady parade of expensive yachts gives Ego Alley its infamous moniker, bringing a unique and ever-changing character to the Annapolis waterfront.

Bloody Point Lighthouse

Bloody Point Bar Lighthouse, known to locals as “Bloody Point Light”, is located just off the southern tip of Kent Island and marks the entrance to the Eastern Bay.

Thomas Point Lighthouse

Thomas Point Shoal Lighthouse, built in 1875, is the only screw-pile lighthouse on the Bay still in its original location and is a National Historic Landmark.

Sailing under the Bay Bridge

While traveling over the bridge gives one a great view of the Bay, traveling under it gives a whole different view and perspective.