Overview
Available languages
2 hours 30 minutes
Mobile ticket
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.
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
ADA accessible with 24-hour notice.
Shade and padded seat provided.
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.
Options
Let's Go Sail Virginia
What‘s Included
CELEBRATE your anniversary or birthday with private seating on a cushion up on the bow.
You'll enjoy a 10% discount for the acclaimed marina restaurant York River Yacht Haven.
PHOTOS offered for free of the entire crew at sea, and on the wheel.
DOGS are welcome, and sometimes they attract dolphins (true fact).
Bring your own box lunch and beverages. Cold bottled water provided.
LEARN to sail by taking the helm (wheel) to turn the boat.
No drugs and no cats!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
132 reviews
Total reviews and rating from Viator & Tripadvisor
Go Sail with Captain Bill- He’s the greatest
pattylG5232UK,Jun 19, 2026
- Review from Tripadvisor
5.00Captain Bill is the most amazing guide. He let my son, Blake, drive the boat & taught him about sailing. It was a truly wonderful experience that I will never forget!!!! He made our trip to Virginia a wonderful memory.
Sailing the Chesapeake.
Freedom110729,Jun 17, 2026
- Review from Tripadvisor
5.00The best experience with perfect weather. Capt Bill turned over the helm to our son who enjoyed 2 perfect hours being our Captain. A few heavy winds but Captain Bob encourage our son to keep steady. He never flinched; just followed directions. We most certainly would do this trip again. Peaceful relaxing day before we left for home. Thanks for giving us a great memory and experience.
Sailing- beginner, but obsessed
ramsieb2026,Jun 16, 2026
- Review from Tripadvisor
5.00If I could give more than 5 stars I would. Sailing with Captain Bill and Let's Go Sailing Virginia was absolutely amazing. My husband had been sailing before, but this was my first time. Captain Bill was patient, knowledgeable and a really good teacher making it a great learning experience. I would recommend the adventure sailing cruise to anyone. It was by far one of the best days of our vacation.
A beautiful day to be remembered
588pam,Jun 9, 2026
- Review from Tripadvisor
5.00We had a wonderful experience sailing on the York River. Captain Bill is welcoming, smart, funny, and knowledgeable. Sailing on the York River on a beautiful sunny day is an experience not to be missed.
A wonderful day of sailing!
588pam,Jun 9, 2026
- Review from Tripadvisor
5.00We sailed with Captain Bill on June 7th 2026 on a beautiful sunny day. It was wonderful! Captain Bill is welcoming, funny, smart, and knowledgeable. Sailing the York River was an unforgettable experience.
Great afternoon in the water.
Burke5,Jun 8, 2026
- Review from Tripadvisor
5.00Bill was a great captain. Had a great afternoon on the water. So enjoyed steering the boat. Highly recommend this trip
Come about, come aboard!
V7375EWstevenc,Jun 6, 2026
- Review from Tripadvisor
5.00Fantastic sailing experience with Capt. Bill! Communication was fantastic for scheduling and arrival instructions. Super friendly and made us feel welcomed and comfortable right away. He taught us some basics of sailing, several of us had a turn at the helm. We loved being able to bring beverages and snacks aboard, it added to the pleasure of being on the water. He also got some fantastic photos from our trip,what a treasure! Price was fantastic! We definitely recommend an outing for a fantastic addition to your vacation!
Do This!
H7808UJsues,May 28, 2026
- Review from Tripadvisor
5.00Wonderful experience. Great day!
Great Sailing and Great Experience!
Venture50952898188,May 28, 2026
- Review from Tripadvisor
5.00I can’t say enough about what a wonderful time we had. Captain Bill communicated weather outlook and conditions the days leading up to our sail and gave us the go ahead the morning of our sail. Since we were traveling from another city this was vital information. He explained everything and added local interest. The experience was as advertised. You can either take the wheel or lounge on deck. Sailing conditions were perfect and it was so very relaxing. We even got to see Dolphins which was quite a treat this early in the season.! Thank you Captain Bill!
Fun day calm waters
U6117RWgails,May 28, 2026
- Review from Tripadvisor
5.00Great excursion would recommend!
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Operated by Williamsburg Charter Sails