3-10 Hour Captained Charters
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
- 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.
Captained charter rates by boat
Captained/crewed charters include a captain and one mate.
The Captains and Mates that we schedule for your charter are independent contractors. While the cost of your charter includes their hourly/daily rate, gratuity (based on the cost of the charter) is customary and expected to be paid by the lead charter guest at the conclusion of the charter.
Aventura 37 Catamaran
| Duration | Price |
|---|---|
| 3 hours | $900 |
| 4 hours | $1,200 |
| 6 hours | $1,450 |
| 8 hours | $1,700 |
| 10 hours | $1,950 |
Dufour 37 “French Kiss”
| Duration | Price |
|---|---|
| 3 hours | $900 |
| 4 hours | $1,000 |
| 6 hours | $1,250 |
| 8 hours | $1,400 |
| 10 hours | $1,550 |
Jeanneau 38 “Southern Cross”
| Duration | Price |
|---|---|
| 3 hours | $700 |
| 4 hours | $800 |
| 6 hours | $900 |
| 8 hours | $1,000 |
| 10 hours | $1,100 |
Hunter 36 “Blue Destiny”
| Duration | Price |
|---|---|
| 3 hours | $650 |
| 4 hours | $725 |
| 6 hours | $800 |
| 8 hours | $875 |
| 10 hours | $950 |
Check availability with our team
Send us your preferred dates and duration through the inquiry form and our team will confirm availability and help set up your sail.
Gallery: 3-10 Hour Captained Charters
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
Pick the boat, duration, and date that best fits your group, then reach out to check availability.
- 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.