Chronic Sailing

Annapolis, United States

Wake to glassy anchorages and fall asleep to the gentle rock of home—a week on the water where comfort never means compromise.

Annapolis, United States

Wake to water lapping your cabin, sleep under stars you've earned—a floating home where the Chesapeake becomes your backyard for a week.

Annapolis, United States

Wake up anchored in crystalline shallows, no crowds, no schedule—just eight of you, steady waters, and a week unfolding exactly as you choose.

Annapolis, United States

Trade your calendar for tides: a week sailing the Chesapeake with people you love, where the only schedule that matters is the water.