Boat charter in Annapolis

Annapolis, Maryland, sits at the heart of the Chesapeake Bay—America's largest estuary and a storied sailing destination. This historic home port offers direct access to one of the continent's most rewarding cruising grounds, where sheltered waters, numerous anchorages, and charming waterfront towns make for unhurried exploration.

The charter fleet comprises eleven vessels suited to varied preferences and experience levels. Five traditional sailing yachts provide classic handling for those seeking wind-powered cruising, while four catamarans deliver stability and spacious deck plans ideal for relaxed group sailing. A single motor yacht and power catamaran round out the lineup, offering fuel-efficient alternatives for guests prioritizing comfort and ease of navigation across the bay's gentle waters.

Whether you're chartering for a weekend escape or a longer voyage, Annapolis provides the perfect departure point for discovering the Chesapeake's quiet coves, historic waterfront communities, and the particular rhythm of East Coast cruising.