Captained or Bareboat Catamaran
Aventura 37 Catamaran
The roomiest option in the fleet, with broad gathering space, multiple staterooms, and a stable catamaran layout for longer Chesapeake Bay trips.
3 staterooms
Chesapeake Bay · Hampton Roads, Virginia
Sailing on the Chesapeake Bay for celebrations, escapes, and time together
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.
The Experience
Exceptional moments on the open water
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.
Private Chesapeake Setting
Your group has space to settle in, enjoy the water, and let the day unfold at its own pace.
Planned Around Your Occasion
Choose the vessel, charter style, and duration that fit the day you are creating.
Details Handled Clearly
Availability, vessel fit, timing, pricing, and final booking details are reviewed before confirmation.
Ways to Sail
Choose Your Way Onto the Bay
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.
Private Celebration
For birthdays, proposals, anniversaries, family gatherings, client outings, and meaningful time on the water.
Plan a Private Event →Longer Time on the Bay
For overnight and multi-day experiences with more room to explore, unwind, and settle into the Chesapeake.
Explore Longer Options →Charter Options
Your Next Adventure Awaits
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.
Captained or Bareboat
Dufour 37 “French Kiss”
A newer Dufour cruiser with accommodations, two staterooms, and the right setup for overnight or multi-day Chesapeake Bay itineraries.
2 staterooms
Captained or Bareboat
Jeanneau 38 “Southern Cross”
A proven cruising yacht with an open cockpit, in-mast furling, and comfortable cabin space for longer Chesapeake Bay charters.
2 staterooms
Captained or Bareboat
Hunter 36 “Blue Destiny”
A flexible Hunter 36 for day sails, overnights, and short getaways, with two private staterooms, a large head, and practical onboard comfort.
2 staterooms
Small-Boat Charter
Colgate 26
A compact, responsive day-sail boat for smaller groups who want a focused sailing experience close to Willoughby Marina.
Small-boat day sail
Ports to Explore
Where the Chesapeake Can Take You
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.
Southern Chesapeake
Norfolk Waterside
Virginia Eastern Shore
Cape Charles
York River
Yorktown
Middle Bay
Annapolis
Eastern Shore
St. Michaels
Southern Maryland
Solomons Island
Occasions
Experiences Tailored To You
A private charter can be shaped around the people, the occasion, and the kind of day you want to create.
Family Days
Bring everyone onto the Bay for a day with room to relax, talk, and enjoy the water.
Anniversaries & Proposals
Plan a private setting with open water, sunset light, and space for the moment.
Birthdays & Celebrations
Give the gathering a setting that feels intentional, scenic, and personal.
Corporate & Client Outings
Host clients, teams, or leadership groups in a private Chesapeake setting.
Visitors to Norfolk
Show guests the Bay from the water with a private sailing experience from Willoughby Marina.
Sunset & Evening Sails
Let golden hour set the tone for a quieter, more atmospheric sail.
Where We Sail
1525 Bayville St
Norfolk, VA 23503
See Hampton Roads and the Chesapeake From a Better Angle
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 Marina1525 Bayville St
Norfolk, VA 23503
Final dock and arrival instructions will be provided after confirmation.
Before You Sail
Know What to Expect Before You Step Aboard
A few simple details make the day easier, especially if this is your first private sailing charter.
What to Wear
Comfortable clothing is recommended. White-soled shoes only.
What to Bring
Bring sunglasses, layers, snacks, drinks, and anything your group needs for comfort during the charter.
Where to Meet
Charters depart from Willoughby Marina at 1525 Bayville St, Norfolk, VA 23503. Final dock instructions will be provided after confirmation.
Weather
Sail Virginia Yacht Charters will advise on weather-related changes, delays, or rescheduling when needed.
Booking Process
How to Book Your Charter
Choose your charter option, select your duration, and complete the booking steps. Some charters may require availability review before final confirmation.
- STEP 1
Choose your charter option
From this page, select the charter, vessel name, or experience that best fits your group.
- STEP 2
Choose your duration
Within the booking portal, choose your dates and times for that charter or vessel.
- STEP 3
Reserve your preferred booking
Provide your preferred date, group size, and contact details.
- STEP 4
Sail Virginia reviews availability
The team checks vessel availability, timing, group size, captain needs, and any manual-review requirements.
- STEP 5
You receive confirmation
Your charter is confirmed only after Sail Virginia Yacht Charters reviews the details and sends final confirmation.
See Charter Options
Availability, pricing, and final booking details are confirmed in the booking system.
Ready to Get Your Group on the Water?
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.