Private Captained Day Charter
Private captained Chesapeake Bay sailing with a licensed captain. Choose 3, 4, 6, 8, or 10 hours for sunsets, celebrations, visiting guests, date nights, or relaxed time on the water.
- Charter type
- Captained Charter
- Capacity
- Up to 6 guests
- Durations
- 3, 4, 6, 8, or 10 Hours
- Departs from
- Willoughby Marina, Norfolk
About this charter
The private captained day charter is a fully crewed Chesapeake Bay sailing experience designed for guests who want time on the water without handling the boat themselves. A licensed captain manages the sailing while your group settles in, takes in the views, and enjoys a private experience built around your pace.
Available durations include 3, 4, 6, 8, and 10-hour charter options. Final availability for each duration is confirmed through the booking process.
This charter works well for sunset sails, casual gatherings, visiting guests, date nights, and easy time on the water with family or friends.
Best for: Couples, families, visitors, small groups, celebrations, and relaxed time on the water.
Gallery: Private Captained Day Charter
Every Sail Is Planned With Care
Sail Virginia Yacht Charters reviews availability, timing, group needs, weather, and final details so each experience feels clear before you arrive and easy once you step aboard.
Learn About Our ApproachAt a glance
- Charter style
- Private captained sailing experience
- Captained
- Licensed captain included
- Duration options
- 3, 4, 6, 8, or 10 hours
- Capacity
- Up to 6 guests
- Pricing
- From $500 for 3 hours. Additional durations confirmed in booking
- Departure
- Willoughby Marina, Norfolk, VA
Details for your sail
Group size
Up to 6 guests.
What to bring
Sunscreen, sunglasses, a layer for cooler evenings, and any food or drinks you'd like aboard.
Footwear
White-soled shoes only
Departure
Charters depart from Willoughby Marina, 1525 Bayville St, Norfolk, VA 23503. Dock and arrival details are provided after confirmation.
Weather
Sail Virginia Yacht Charters will advise on weather-related changes, delays, or rescheduling when needed.
Things to know
Minimum Charter Duration
Private captained day charters start at a 3-hour minimum.
Sailing Requirements
No sailing experience is needed. A licensed captain is included and handles the vessel.
Cancellation Policy
Cancellation fees may apply.
Captain Included
This is a captained charter option. Guests can relax while the captain handles the vessel and route details.
Group Size
Up to 6 guests.
Available Durations
Available durations include 3, 4, 6, 8, and 10-hour charter options. Final availability and pricing are confirmed through the booking process.
Best For
Couples, families, visitors, small groups, celebrations, and relaxed time on the water.
Departure Location
Charters depart from Willoughby Marina, 1525 Bayville St, Norfolk, VA 23503. Final dock and arrival instructions are provided after confirmation.
What to Wear
Comfortable clothing is recommended. White-soled shoes only.
Weather Conditions
Sailing is subject to weather conditions and safety review. Sail Virginia Yacht Charters will advise on weather-related changes, delays, or rescheduling when needed.
Arrival Time
Please arrive at least 15 minutes before departure. Final arrival and dock instructions will be provided after confirmation.
Frequently asked questions
Please arrive at least 15 minutes before departure. Sailing is subject to weather conditions and safety review.
What Happens After You Request a Charter
- STEP 1
Choose your boat and charter option
Use the booking widget to select your preferred boat, then pick the duration and date 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.