Let's Go Sail Virginia
Overview
Few people get out on the water these days, and fewer still get to sail a modern sailboat. Here is the single-most unique activity in Williamsburg, where guests get to run the helm or just relax on the water.
Unlike crowded tourist boats, every charter here is 100% private. Guests can steer the yacht, trim the sails, or simply relax while taking in wide‑open river views, local wildlife, and the steady coastal breeze that makes the York River the best sailing waterway in the region. Dolphin sightings are common in warm months.
Perfect for:
• Couples seeking a unique, romantic experience
• Families wanting a safe, private adventure
• History lovers exploring Williamsburg and Yorktown
• Photographers and wildlife enthusiasts
• Anyone looking for the best sailing near Williamsburg, VA
Whether you’re celebrating a special occasion or simply want to experience the York River under sail, this is the region’s top‑rated, most authentic sailing experience.
What's Included
- Dinner You'll enjoy a 10% discount for the acclaimed marina restaurant York River Yacht Haven.
- Lunch Bring your own box lunch and beverages. Cold bottled water provided.
- CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
- PHOTOS offered for free of the entire crew at sea, and on the wheel.
- DOGS are welcome, and sometimes they attract dolphins (true fact).
- LEARN to sail by taking the helm (wheel) to turn the boat.
- No drugs and no cats!
Meeting Location
8109 Yacht Haven Road
Gloucester Point, VA 23062, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
1. You'll learn to sail in 10 minutes. From there you'll learned the details of how to build speed, how to "see the wind" and how to turn the boat safely.
2. Special Events include Appreciation Cruise, Boat-Buying Cruise, Waterfront Real Estate Cruise, Wedding Engagements, Anniversaries, Birthdays, Burials at Sea.
4. Bring your dog for free and save on kennel fees. No cats!
5. Sit back and relax, or seize the bow in privacy for couples.
Additional Info
- Confirmation is instant and will be received at time of booking
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- ADA accessible with 24-hour notice.
- Shade and padded seat provided.
- This tour/activity will have a maximum of 6 travelers
Frequently Asked Questions (8)
Q: What is the cancellation policy for the Let’s Go Sail Virginia?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-211668P2
Traveler Photos
Reviews
Average 4.96 out of 5 stars based on 197 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from Cool Shore Excursions customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- Dinner. You'll enjoy a 10% discount for the acclaimed marina restaurant York River Yacht Haven.
- Lunch. Bring your own box lunch and beverages. Cold bottled water provided.
- CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
- PHOTOS offered for free of the entire crew at sea, and on the wheel.
- DOGS are welcome, and sometimes they attract dolphins (true fact).
- LEARN to sail by taking the helm (wheel) to turn the boat.
- No drugs and no cats!.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age to participate is 1. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Let's Go Sail Virginia is as follows:
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Let’s Go Sail Virginia will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- DinnerYou'll enjoy a 10% discount for the acclaimed marina restaurant York River Yacht Haven.
- LunchBring your own box lunch and beverages. Cold bottled water provided.
- CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
- PHOTOS offered for free of the entire crew at sea, and on the wheel.
- DOGS are welcome, and sometimes they attract dolphins (true fact).
- LEARN to sail by taking the helm (wheel) to turn the boat.
- No drugs and no cats!
Additional Info
- Confirmation is instant and will be received at time of booking
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- ADA accessible with 24-hour notice.
- Shade and padded seat provided.
- This tour/activity will have a maximum of 6 travelers
