Enjoy the Bay while a licensed captain handles the sailing. Choose from available captained charter options, select your preferred duration, and confirm final availability through the booking process.
A captained sail gives your group a private Chesapeake Bay setting with the sailing handled for you. Step aboard, settle in, and enjoy the water while the captain manages the vessel, route, and conditions.
A licensed captain manages the vessel, route, docking, and on-water decisions so guests can enjoy the experience.
Captained charters are designed for guests who want to enjoy the Bay without operating the vessel.
Choose from available captained vessels and duration options based on your group, occasion, and preferred time on the water.
Each vessel offers a different way to experience the Chesapeake with a captain handling the sailing. Final availability, pricing, group size, and booking details are confirmed through the booking process.
Available Captained or Bareboat
A comfortable cruising yacht available for captained or bareboat sailing on the Chesapeake Bay. Up to 6 guests; overnight captained reservations may be limited to 2 or 4 guests because the captain requires a berth.
Available Captained or Bareboat
A spacious catamaran available captained or bareboat, suited for groups looking for more room and longer time on the Bay. Up to 6 guests for day sails and bareboat overnight; overnight captained reservations are limited to 4 guests because the captain requires a berth.
Captained Charter Available · Bareboat Availability Pending Review
The DuFour 37 “French Kiss” is available as a captained charter option.
Captained Cruise · 3 Hours
A 3-hour captained cruise aboard the Colgate 26 for smaller groups looking for a focused Chesapeake Bay sailing experience. Up to 6 guests.
The captain manages the sailing side of the experience so your group can focus on the water, the occasion, and the people aboard.
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.
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.
