Choose your vessel, select your charter length, and plan a private sailing experience from Willoughby Marina in Norfolk.
Captained and bareboat options available. Charter durations vary by vessel.
Departing from Willoughby Marina in Norfolk, Virginia.
When your group steps aboard, the day takes a different pace. The marina falls behind, the water opens up, and the Chesapeake becomes the setting for lasting memories. We help with the vessel, timing, and final details so the experience feels effortless and hard to forget.
Your group has space to settle in, enjoy the water, and let the day unfold at its own pace.
Choose the vessel, charter style, and duration that fit the day you are creating.
Availability, vessel fit, timing, pricing, and final booking details are reviewed before confirmation.
Every group comes to the water for a different reason. Start with the experience you have in mind, then choose the vessel, duration, and booking path that fit your plans.
For birthdays, proposals, anniversaries, family gatherings, client outings, and meaningful time on the water.
Plan a Private Event →For overnight and multi-day experiences with more room to explore, unwind, and settle into the Chesapeake.
Explore Longer Options →Select the charter option that best fits your group. Each vessel shows the available duration options, from short sails to overnight and multi-day requests.
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
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.
A private charter can be shaped around the people, the occasion, and the kind of day you want to create.
Bring everyone onto the Bay for a day with room to relax, talk, and enjoy the water.
Plan a private setting with open water, sunset light, and space for the moment.
Give the gathering a setting that feels intentional, scenic, and personal.
Host clients, teams, or leadership groups in a private Chesapeake setting.
Show guests the Bay from the water with a private sailing experience from Willoughby Marina.
Let golden hour set the tone for a quieter, more atmospheric sail.
Depart from Willoughby Marina in Norfolk and experience the Southern Chesapeake Bay from the water — open air, waterfront views, wildlife, sunsets, and the quiet shift that happens once land falls behind you.
Willoughby MarinaFinal dock and arrival instructions will be provided after confirmation.
A few simple details make the day easier, especially if this is your first private sailing charter.
Comfortable clothing is recommended. White-soled shoes only.
Bring sunglasses, layers, snacks, drinks, and anything your group needs for comfort during the charter.
Charters depart from Willoughby Marina at 1525 Bayville St, Norfolk, VA 23503. Final dock instructions will be provided after confirmation.
Sail Virginia Yacht Charters will advise on weather-related changes, delays, or rescheduling when needed.
Choose your charter option, select your duration, and complete the booking steps. Some charters may require availability review before final confirmation.
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.
Availability, pricing, and final booking details are confirmed in the booking system.
From a short captained sail to a multi-day Chesapeake Bay charter, start with your preferred option and the team will help confirm the right fit.
Final availability, pricing, and booking details are confirmed through the booking system.
