Sail Virginia Yacht Charters offers private captained and bareboat sailing charters on the Chesapeake Bay, departing from Willoughby Marina in Norfolk, Virginia. The business helps guests choose the vessel, timing, and charter style that fit the occasion, whether that’s a quick sunset sail, a private celebration, or a multi-day voyage exploring the wider Chesapeake.
The fleet includes five vessels suited to different group sizes and trip lengths. The Aventura 37 Catamaran is the roomiest option, with three staterooms and a stable layout for longer trips, available captained or bareboat from 3 hours up to 7 days. The Dufour 37 “French Kiss” and Jeanneau 38 “Southern Cross” both offer two staterooms and comfortable cabin space for overnight or multi-day Chesapeake itineraries, also captained or bareboat. The Hunter 36 “Blue Destiny” offers flexible day sails, overnights, and short getaways with two private staterooms and a large head. For smaller groups wanting a focused, closer-to-marina experience, the compact Colgate 26 offers a responsive 6-hour day sail.
Longer charters open up destinations across the Southern Chesapeake, Norfolk Waterside, Virginia’s Eastern Shore, Cape Charles, the York River, Yorktown, and further up the bay to Annapolis, St. Michaels, and Solomons Island, with routes reviewed based on vessel, duration, weather, and booking details.
Pricing starts from $400 for the Colgate 26, $550 for a 3-10 hour captained charter or the Hunter 36, $600 for the Jeanneau 38, and $800 for the Aventura 37 catamaran or Dufour 37, with multi-day rates available for longer trips. Guests are asked to wear white-soled shoes and bring sunglasses, layers, snacks, and drinks for comfort during the charter.
For anyone in the Norfolk/Hampton Roads area looking for a private sailing charter on the Chesapeake Bay, from a short sunset sail to a multi-day voyage, Sail Virginia Yacht Charters offers a well-equipped, multi-vessel fleet departing from Willoughby Marina.
