Private Sailing on the Chesapeake Bay
Sail Virginia Yacht Charters offers private captained and bareboat sailing experiences from Willoughby Marina in Norfolk, Virginia. Every booking is reviewed for vessel fit, timing, group needs, and final details before confirmation.
Our Approach
A Clearer Way to Plan Time on the Bay
Planning a private sailing experience should feel straightforward. The team helps guests choose the right vessel, duration, and booking path based on the group, occasion, and time they want on the water. From short captained sails to longer bareboat options, the process is designed to keep the next step clear before the charter is confirmed.
The Fleet
Vessels for Different Ways to Sail
The fleet includes options for captained sailing, smaller day-sail experiences, bareboat monohull sailing, bareboat catamaran cruising, and new charter offerings as they are confirmed. Each vessel supports a different kind of day on the Chesapeake, from easy hourly sails to overnight and multi-day requests.
Where We Sail
Departing from Willoughby Marina
Sail Virginia Yacht Charters operates from Willoughby Marina at 1525 Bayville St, Norfolk, VA 23503. The location offers direct access to Hampton Roads and the Southern Chesapeake Bay for short sails, private occasions, sunset outings, overnight experiences, and longer sailing requests.
Willoughby Marina
1525 Bayville St
Norfolk, VA 23503
Final dock and arrival instructions are provided after confirmation.
What Guests Can Expect
The Details Stay Clear
Private Group Experience
Your booking is planned around your group, vessel selection, duration, and confirmed charter details.
Flexible Charter Lengths
Charter durations vary by vessel — from short day sails to multi-day rentals. See each boat's listing for available options.
Captained and Bareboat Options
Captained options are handled by a licensed captain. Bareboat options are reviewed for qualified sailors before confirmation.
Clear Arrival Details
Final dock location, arrival timing, and booking instructions are provided after confirmation.
Weather-Aware Scheduling
Sail Virginia Yacht Charters will advise on weather-related changes, delays, or rescheduling when needed.
FAQ
Common Questions Before You Sail
A few practical details can make planning easier. Final availability, timing, payment instructions, and dock details are confirmed through the booking process.
Ready to Plan Your Time on the Bay?
Choose your vessel, duration, and preferred date. The team will review availability, pricing, timing, and final booking details before confirmation.