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Nautical chart of the Chesapeake Bay

While it is nice to have a sense of how far one could go during a half day versus a full day, we are very much at the mercy of wind and weather. Sailing is an activity which demands flexibility, as our course and speed are dictated by the wind and results may vary.

Full Day:  ~6 hrs

  • Sail to the Chesapeake Bay BridgeThomas Point Light, and back to Annapolis, approximately 20 miles.
  • Sail to Whitehall Bay, drop the anchor, enjoy a picnic, take a swim, and then sail home.
  • Sail up the Severn River to Round Bay, cruise through Annapolis Harbor, take a trip down Ego Alley, and return.
  • Sail to Poplar Island passing Thomas Point Light, Bloody Point LightBay Bridge, and home.
  • Morning sail to the Bridge, anchor for lunch, swim/kayak/paddleboard, sail to Thomas Point, cruise Annapolis Harbor and Ego Alley.
  • Sail to Harness Creek, anchor for lunch, swim/kayak/paddleboard, sail back via Bloody Point or Bay Bridge.

Absent favorable winds

Worst case, we do have an engine and can take a slow boat ride to any of these destinations. Just being on the water, away from the hustle and bustle, ghosting along in the peace and quiet while soaking up the scenery can be a really great experience.