Pick the vessel that fits your group. Each option opens its own page with photos, durations, and booking.
From $500
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
From $2,800
The roomiest option in the fleet, with broad gathering space, multiple staterooms, and a stable catamaran layout for longer Chesapeake Bay trips.
Available from 2 days / 30 hours to 7 days
3 staterooms
From $2,000
A newer Dufour cruiser with clean accommodations, two staterooms, and the right setup for overnight or multi-day Chesapeake Bay itineraries.
Available from 2 days / 30 hours to 7 days
2 staterooms
From $1,600
A proven cruising yacht with an open cockpit, in-mast furling, and comfortable cabin space for longer Chesapeake Bay charters.
Available from 2 days / 30 hours to 7 days
2 staterooms
From $500
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
From $400
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.
From this page, select the charter, vessel name, or experience that best fits your group.
Within the booking portal, choose your dates and times for that charter or vessel.
Provide your preferred date, group size, and contact details.
The team checks vessel availability, timing, group size, captain needs, and any manual-review requirements.
Your charter is confirmed only after Sail Virginia Yacht Charters reviews the details and sends final confirmation.
