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Let's Go Sail the York River in Gloucester Point, Virginia

158 Reviews 4.95 out of 5 stars Based on 158 traveler reviews collected by Cool Destinations and TripAdvisor |
Recommended by 99% of reviewers
99% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Virginia, USA
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from $96.42 per person

Lowest Price Guarantee
Couples enjoy a romantic cruise.
Take the wheel or sit in the catbird seat.
Learn to sail in ten minutes.
Enjoy a romantic interlude.
See the world from the catbird seat.

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Don't miss out!
On average, this is booked 11 (1) days in advance.
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2 hours 30 minutes (approx.)
Mobile ticket
Instant confirmation
Offered in: English

Overview

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, birthday, anniversary or surprise gift.

Private, hands‑on sailing on the beautiful York River just minutes from Williamsburg. Steer the boat, learn local history, spot dolphins, or simply relax. A peaceful, unforgettable experience for couples, families, and anyone seeking the region’s top sailing adventure.

What's Included

  • Bottled water
  • Privacy on a cushion up on the bow.
  • Learn to sail in 20 minutes. Grab the helm!
  • Absolutely no illegal drugs onboard.
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Meeting Location

Meeting point

8109 Yacht Haven Road
Gloucester Point, VA 23062, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Experience the region’s top‑rated private sailing adventure just minutes from Williamsburg and Yorktown. Step aboard a comfortable 32‑ft sloop for a peaceful, hands‑on sail on the beautiful York River, where steady breezes, open water, and stunning views create the best sailing conditions in Tidewater Virginia. Every charter is fully private (up to 6 people max), giving you the freedom to steer the boat, learn sailing basics, or simply relax on deck. Spot dolphins in warm months, enjoy wide‑open river scenery, and escape the crowds for an unforgettable experience perfect for couples, families and anyone seeking authentic coastal adventure. Great for romantic getaway.

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Transportation options are wheelchair accessible
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap

Frequently Asked Questions

(8)

Q: Will I get seasick on Let’s Go Sail the York River in Gloucester Point, Virginia?

A: If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy. Read more Feb 2023

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-211668P1

Traveler Photos

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Reviews

4.95
158 reviews

Average 4.95 out of 5 stars based on 158 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor

5 stars
154
4 stars
2
3 stars
1
2 stars
0
1 star
1

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On average, this is booked 11 (1) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool Destinations customers.

Filter by:

Q: Will I get seasick on Let’s Go Sail the York River in Gloucester Point, Virginia?
A:

If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.

Feb 2023
Q: What is the cancellation policy for the Let’s Go Sail the York River in Gloucester Point, Virginia?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • 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 (EDT).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Bottled water.
  • Privacy on a cushion up on the bow.
  • Learn to sail in 20 minutes. Grab the helm!.
  • Run the helm as you learn to sail. Hoist the spinnaker for downwind sailing. Swim off the aft if the wind dies.
  • Photos provided for free of your excursion.
The following is NOT included:
  • Absolutely no illegal drugs onboard.
Apr 2025
Q: What is the weather cancellation policy?
A:

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 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 1. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If 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 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Let's Go Sail the York River in Gloucester Point, 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
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Let’s Go Sail the York River in Gloucester Point, Virginia will be included in your confirmation email from Cool Destinations. 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 2024

What's Included

Activity name

  • Bottled water
  • Privacy on a cushion up on the bow.
  • Learn to sail in 20 minutes. Grab the helm!
  • Run the helm as you learn to sail. Hoist the spinnaker for downwind sailing. Swim off the aft if the wind dies.
  • Photos provided for free of your excursion.
  • Absolutely no illegal drugs onboard.

Additional Info

Activity name

  • 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
  • Infants are required to sit on an adult’s lap
  • Friendly dogs welcomed.
  • This tour/activity will have a maximum of 6 travelers
  • Operated by a business

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For your protection and stress-free bookings, use our secure platform to pay for bookings. Williamsburg Charter Sails

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  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
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  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Destinations and 48 hours before your trip starts, we will refund the difference.
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100% refund
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You can cancel up to 24 hours in advance of the tour for a full refund.

  • 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 (EDT).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

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If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Destinations over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
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  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.