Photo Shoots
3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 92% of travelers
92% of reviewers gave this product a bubble rating of 4 or higher.
from
$97
per adult
Williamsburg Charter Sails
Williamsburg Charter Sails
5
11:00 AM - 2:00 PM, 2:30 PM - 5:30 PM
Monday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Tuesday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Wednesday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Thursday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Friday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Saturday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Sunday
11:00 AM - 2:00 PM
2:30 PM - 5:30 PM
Full view
About
Enjoy the Zen experience of a private yacht that is safe, clean and easy to sail. Take the wheel or bring a bottle of wine. Up to six people sail the York River for three hours to see the scenery and learn a short history of the Battle of Yorktown from the perspective of the water. Join us any day of the week at York River Yacht Haven, 8109 Yacht Haven Road, Gloucester VA 230612. COVID-19 – Virginia reopened May 15 for sailing and fishing charters. He will meet you at the marina with a mask, removing it once we board the boat. We provide free masks for those who want one, and we practice social distancing.
Williamsburg, Virginia
Awards
Travelers' Choice
2024
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Improve this listingTours and Tickets by Williamsburg Charter Sails
Sailing
3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 99% of travelers
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$97
per adult
Travelers talk about
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
5.0
734 reviews
Excellent
714
Very good
16
Average
2
Poor
0
Terrible
2
512teri
Newport News, VA1 contribution
Apr 2021
I had a perfect time! The sailing was safe & the company stellar. The weather could not have been nicer on an early spring day April 6th. We had 12 MPH breezes & the Hunter 32 flew along hitting 16-17 at times; yet at a comfortable angle of inclination “heel.” I strongly recommend this capable captain to go sailing with. He is an engaging personality and I was totally comfortable with his abilities; speaking as a sailor with 20 years experience.
Written April 16, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Theresa for those sterling remarks, especially coming from a 20-year sailor.
Written April 21, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Rberg79
Topeka, KS1 contribution
Jun 2021 • Family
Captain Bill was professional and friendly right from the start.
It was my family's first time sailing and to the Williamsburg area. He shared a wealth of information not only about sailing but also the area. He assured my wife (who doesn't like boats) that things were fine when certain things would happen and explained what was happening. Two of my son's took the helm for large periods of time. They were clueless at the start but towards the end they were sailing smoothly due to Captain Bills teaching.
We had a great time at a great value for a family of 5 ages from 13-41
The voyage was exciting, fun, relaxing, knowledgeable, interactive, and engaging.
I highly recommend checking him out
It was my family's first time sailing and to the Williamsburg area. He shared a wealth of information not only about sailing but also the area. He assured my wife (who doesn't like boats) that things were fine when certain things would happen and explained what was happening. Two of my son's took the helm for large periods of time. They were clueless at the start but towards the end they were sailing smoothly due to Captain Bills teaching.
We had a great time at a great value for a family of 5 ages from 13-41
The voyage was exciting, fun, relaxing, knowledgeable, interactive, and engaging.
I highly recommend checking him out
Written June 8, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Robert for such an extensive review, especially for citing the voyage as exciting, fun, relaxing, knowledgeable, interactive and engaging. Wow!
Written June 9, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
coreys311
New York City, NY4 contributions
Oct 2021 • Couples
Captain Bill was so accommodating, friendly and safe. He took my wife, dog, and myself out on his boat and despite the bit of rain we encountered, he kept us engaged, laughing, safe and enjoying our time. Great conversation all around and it got quite zen when the rain stopped. Would recommend Captain Bill to anyone I know. Great time!
Written November 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Corey for such a glowing review. Loved the zen comment too.
Written November 7, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
missymarie123
Pittsburgh, PA1 contribution
May 2021
Captain Bill was great! My fiance and I booked an adventure cruise since we wanted to spend some time out on the water during our visit to Williamsburg. We had a great time! The weather was beautiful and the sailing trip was fun, relaxing, and informative all at once! We got to assist in sailing the boat as well as spend some time relaxing and soaking up the sun. We got engaged earlier on our trip and Captain Bill even had us "reenact" our engagement with a ring that he had on board for a great photo opportunity! Overall it was a really fun experience, we loved it! Would highly recommend!
Written June 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Missy, especially for describing the sailing as fun, relaxing and informative all at once. Others cheered your reprised engagement.
Written June 3, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Dianne J
Lawrenceville, GA2 contributions
Jun 2021 • Couples
Among other things in his former life, Captain Bill O'Donovan was a newspaper publisher, hence the name of his beautiful, two-masted sailboat, "Deadline." By luck, my husband and I were his only guests on this afternoon's history sail on the York River.
Bill is a serious history buff, and as any good journalist, he enjoys digging to get the backstory and details that most historical tours don't know (or don't choose to share.) He is an enthusiastic storyteller and paints vivid word pictures, bringing history to life as you sail where it literally took place.
Bill encourages his guests to take as active or passive role as they like in participating in the sailing experience and even takes photos for you to commemorate your sail.
By far, the most personable, genuine and uniquely informative water tour we've taken.
Bill is a serious history buff, and as any good journalist, he enjoys digging to get the backstory and details that most historical tours don't know (or don't choose to share.) He is an enthusiastic storyteller and paints vivid word pictures, bringing history to life as you sail where it literally took place.
Bill encourages his guests to take as active or passive role as they like in participating in the sailing experience and even takes photos for you to commemorate your sail.
By far, the most personable, genuine and uniquely informative water tour we've taken.
Written June 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Dianne, particularly for describing it as the most personable, genuine and uniquely informative water tour you've taken. Wow!
Written June 3, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
GiselaHarmatz
1 contribution
Jul 2021 • Family
Family members visited from out of state and we sailed with Capt. Bill in mid July and had a fantastic time.
Our son was allowed to take the wheel and has now developed a passion for sailing. Capt. Bill did an excellent job pointing out various seabirds along the way and we even spotted dolphins near the Coleman Bridge.
We are planning on going on another sailing adventure soon!
Our son was allowed to take the wheel and has now developed a passion for sailing. Capt. Bill did an excellent job pointing out various seabirds along the way and we even spotted dolphins near the Coleman Bridge.
We are planning on going on another sailing adventure soon!
Written July 19, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Gisela, especially that your son has now developed a passion for sailing. Wow!
Written July 20, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
ERP444
San Antonio Tlayacapan, Mexico28 contributions
May 2021 • Family
Despite rather unsettled weather with brisk winds and choppy water, we had a wonderful morning with Captain Bill. He is a true professional and modified our outing to minimize the rough conditions. His knowledge of the history of the Battle of the Capes was truly impressive. I would not hesitate for a moment to recommend Williamsburg Charter Sails to anyone wanting a great sailing experience!
Written May 26, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Ted, and for referring to a great sailing experience.
Written May 27, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Sightsee813139
1 contribution
Apr 2022
I am a former sailboat owner. Williamsburg Charter Sails owned and operated by
William ODonnell is a a first rate boat owner and operator. We sailed in light rain, strong winds, gusty winds, and very light winds. Mr. ODonnell is an experienced skilled sailor. He has great knowledge of the local waters and how to make the experience entertaining and filled with information. He has great interpersonal skills. He owns a great Hunter 32' in great condition that looks new. I can't wait to go again and i my have to hurry. I'm eighty.
William ODonnell is a a first rate boat owner and operator. We sailed in light rain, strong winds, gusty winds, and very light winds. Mr. ODonnell is an experienced skilled sailor. He has great knowledge of the local waters and how to make the experience entertaining and filled with information. He has great interpersonal skills. He owns a great Hunter 32' in great condition that looks new. I can't wait to go again and i my have to hurry. I'm eighty.
Written April 21, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much for such an extensive review, especially the headline.
Written April 23, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Michael-VirginiaUSA
Henrico, VA48 contributions
Jul 2021
An incredible trip. Bill is a polished professional who puts you at ease right away. Had not previously sailed so unsure of what to expect. Chose the history themed tour and Bill did not disappoint. Very thorough narrative of the history of Yorktown and the surrounding waters of the York River, complete with visual displays. While impressed with the history, the best was yet to come.
Bill turned the voyage over to willing passengers and I was the fortunate recipient of 1-1/2 - 2 hours at the helm and Bill provided me with an unbelievable education on sailing.
Have referred Bill to multiple friends and he has a lifelong client here. The $150 3 hour excursion for a couple was a great value. Cannot wait to go again. Ahoy Bill and happy sailing!
Bill turned the voyage over to willing passengers and I was the fortunate recipient of 1-1/2 - 2 hours at the helm and Bill provided me with an unbelievable education on sailing.
Have referred Bill to multiple friends and he has a lifelong client here. The $150 3 hour excursion for a couple was a great value. Cannot wait to go again. Ahoy Bill and happy sailing!
Written July 26, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Michael, particularly for describing it as an unbelievable education on sailing.
Written July 27, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
nelmslaw
Richmond, VA1 contribution
May 2021
I highly recommend Williamsburg Charter Sails...we spent a perfect day out on the water with Capt. Bill, who was extremely knowledgeable and kind. He took the time to explain the aspects of sailing as well as the local history. We will definitely be sailing again!
Written May 23, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks very much Lee, especially for the headline and describing it as a perfect day on the water.
Written May 25, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
HI Bill,
We are coming here for Springbreak. There will be 7 of us. We are all family. I have a 10,12 and 14 years old.
What do you charge and how long is it? It looks amazing!
Thanks,
Beth Petty
Written February 5, 2017
Alas, the US Coast Guard limits me to six people at a time. We can take six instead of seven, or four on one trip and three on another , or any other permutation. Sails depart at 11 am and 2:30, lasting 3 hours. Couples of two $150, three people $225, family of four, five and six $250. Mondays and Tuesdays are discounted 15% and 10% respectively. Thanks for asking.
Written February 5, 2017
Why would someone above ask if there was a place to eat, do you stop and wait for people to eat. we are coming the week of the 4th and are very interested. How many are on board and there are only two of us, will there be others? How far is this from the inns at Colonial Williamsburg and why are people asking if you pick them up? are there shuttles? thanks so much, judy
Written September 29, 2015
Judy-
1. We don't stop for people to eat. They typically buy fast food and bring it aboard. We also have an excellent restaurant at the marina for lunch afterward.
2. I have openings the week of Oct. 4.
3. Usually another couple joins us, but sometimes you have it all to yourselves.
4. We're 30 minutes from the inns at Colonial Williamsburg, via the majestic Colonial Parkway. I provide full directions. I do not believe CW has shuttle service for this amenity.
5. For more details, call 757-876-8654.
Thanks,
Capt. Bill
Written September 29, 2015
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