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
Charter Selector
Choose Your Vessel
Pick the vessel that fits your group. Each option opens its own page with photos, durations, and booking.
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
Not sure which option fits? Send us a quick note with your date, group size, and occasion, and the team will recommend a vessel.
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
Booking Process
What Happens After You Request a Charter
- STEP 1
Choose your charter option
Browse the fleet and find the charter, vessel, or experience that best fits your group.
- STEP 2
Reach out to check availability
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.
- STEP 3
Sail Virginia checks availability
The team reviews vessel availability, timing, group size, and captain needs for the dates you requested.
- STEP 4
We plan the day together
A team member works with you directly to finalize the vessel, schedule, and any details for your sail.
- STEP 5
You receive confirmation
Your charter is confirmed only after Sail Virginia Yacht Charters reviews the details and sends final confirmation.