Pick the vessel that fits your group. Each option opens its own page with photos, durations, and booking.
Settle in for a few hours on the Bay while the captain handles the sailing, route, and timing. Built for sunsets, celebrations, visiting guests, date nights, and easy time together.
Available from 3 hours to 10 hours
Day sail
The roomiest option in the fleet, with broad gathering space, multiple staterooms, and a stable catamaran layout for longer Chesapeake Bay trips.
Available from 3 hours to 7 days
3 staterooms
A newer Dufour cruiser with accommodations, two staterooms, and the right setup for overnight or multi-day Chesapeake Bay itineraries.
Available from 3 hours to 7 days
2 staterooms
A proven cruising yacht with an open cockpit, in-mast furling, and comfortable cabin space for longer Chesapeake Bay charters.
Available from 3 hours to 7 days
2 staterooms
A flexible Hunter 36 for day sails, overnights, and short getaways, with two private staterooms, a large head, and practical onboard comfort.
Available from 6 hours to 3 days
2 staterooms
A compact, responsive day-sail boat for smaller groups who want a focused sailing experience close to Willoughby Marina.
Available for 6 hours
Small-boat day sail
Not sure which option fits? Send us a quick note with your date, group size, and occasion, and the team will recommend a vessel.
From Hampton Roads to the Eastern Shore, the Middle Bay, and historic towns farther up the Chesapeake, longer charters open the door to a wide range of waterfront destinations. Routes are reviewed based on vessel, duration, weather, and final booking details.
Browse the fleet and find the charter, vessel, or experience that best fits your group.
Submit the inquiry form, call the office, or send an email with your preferred date, duration, and group size. Charters are not booked directly on this site.
The team reviews vessel availability, timing, group size, and captain needs for the dates you requested.
A team member works with you directly to finalize the vessel, schedule, and any details for your sail.
Your charter is confirmed only after Sail Virginia Yacht Charters reviews the details and sends final confirmation.
