Step back into history when you join the crew of the Yorktown Schooner Alliance. Lend a hand at setting sail, take the helm and steer the ship, or look for dolphins and osprey as you glide along the shores of the York River. You will relive sailings Golden Age as you cruise past the Victory Monument and Battlefield where our country won its independence.
Setting sail on the historic waters of Yorktown, VA is a magical experience. Let yourself fall into the rich surrounding history and the majestic ship you're aboard while amongst family and friends - a fresh breeze pulling it all together. It's our passion at Yorktown Sailing Charters to introduce you to the beauty of the waters we've been sailing for over 30 years, give you lifelong memories and keep you coming back for more.
Setting sail on the historic waters of Yorktown, VA is a magical experience. Let yourself fall into the rich surrounding history and the majestic ship you're aboard while amongst family and friends - a fresh breeze pulling it all together. It's our passion at Yorktown Sailing Charters to introduce you to the beauty of the waters we've been sailing for over 30 years, give you lifelong memories and keep you coming back for more.
Services
Join the Alliance and step back into history aboard this 105 foot gaff-rigged schooner. The Alliance offers sailing charters from Yorktown Virginia in the summer months and Caribbean Islands in the winter months. This is your opportunity to explore the Chesapeake Bay tidewaters for a sightseeing cruise, or for the more adventurous soul, explore the emerald waters of the Caribbean on a 7 day cruise.
Four centuries ago, Captain John Smith explored the waters around Yorktown aboard a small sailing vessel while trading with the Powhatan Indians. Join him in spirit when you sail aboard Yorktown's Schooner Alliance. On the Historic Yorktown cruises you will sail past the Yorktown Battlefield where our country won its independence, and relive sailings golden age when a young America clambered aboard vessels similar to Alliance to find adventure.
For the more adventurous traveler who wants to get away from it all you should join the Alliance for a Caribbean sailing voyage. We will be departing the Chesapeake Bay in early December and sailing straight for Bocas del Toro Panama. From there we will make our way back to the Chesapeake Bay in short ocean passages stopping at some beautiful off-the beaten-path islands that offer great snorkeling, diving and hiking!
If you are vacationing in the Caribbean and are looking to spend a relaxing week with your friends and family, you have come to the right place. Yorktown Sailing Charters is your source for a number of Caribbean cruises for you to enjoy on your next vacation. With over 30 years of sailing experience, your hosts will take you on the trip of your lifetime.
These trips encompass a variety of different experiences including some ocean voyaging and exploring new ports. You will be standing watch and participating as part of the crew, including helping in the galley with cooking and cleaning, steering and standing lookout, helping set and trim sails, etc.
Reviews (21)
Gerry Renner
Oct 23, 2021
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Melanie Jean Gomez
Oct 22, 2021
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The sunset sailing charter was a perfect ending to a beautiful day in Yorktown! The crew were super polite and made the sailing the highlight of my day! I loved the historical information they shared and how they involved the passengers to hoist the sails. We even got to see some dolphins! I am super impressed with the crew and the schooner!
Mark Lyons
Oct 10, 2021
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Beth Winslow
Sep 30, 2021
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John Baldwin
Sep 17, 2021
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Rob T.
Aug 18, 2021
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WHAT a Waste if Time
AND don't go, if it's hot.
It takes the crew forever to get away from the dock.
We went on the Pirate Cruise with
2 kids and 9 adults.
The owner was aboard,
Not dressed in "Pirate Dress"...
But was constantly commanding her crew of "new pirates"
One of her crew, was there, it was his first day, and he was not dressed in Pirate Dress either.
We spent a lot of money,
For Nothing.
The kids got to,
Help lift the sails,
and watch a cannon fire,
The kids did take turns at the helm,
But the captain didn't have the motor in gear.
SAD trip
AND don't go, if it's hot.
It takes the crew forever to get away from the dock.
We went on the Pirate Cruise with
2 kids and 9 adults.
The owner was aboard,
Not dressed in "Pirate Dress"...
But was constantly commanding her crew of "new pirates"
One of her crew, was there, it was his first day, and he was not dressed in Pirate Dress either.
We spent a lot of money,
For Nothing.
The kids got to,
Help lift the sails,
and watch a cannon fire,
The kids did take turns at the helm,
But the captain didn't have the motor in gear.
SAD trip
William Crowder
Aug 13, 2021
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Genevieve M.
Jul 04, 2021
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Very underwhelming. We booked the pirate cruise for the kids on July 4th. The experience was a disappointment for all. I would not recommend. Captain honestly seemed high. "Mates" seemed disinterested in their jobs and entire experience didn't feel geared towards young kids at all. No laughter or fun by staff. Music, jokes, props, excitement would make the experience worth the cost. We all couldn't wait to get off.
Ernie L.
Jun 19, 2021
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Dorothy F.
Jun 19, 2021
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We went on the 1.30 cruise and we're a bit disappointed as we expected a cruise down the river and they only went back and forth between the beach and across the river. At the end they did go under the bridge a bit and back. But it was not what we expected and paid for. We did see a destroyer go through the bridge and the opening and closing of it. So that was exciting for our granddaughter. Just wish we knew the route before we paid.
Tiffany J.
Sep 14, 2020
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Kurt P.
Jul 23, 2020
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The girlfriend and I decided to give this a try, we were not disappointed, but it could have been slightly better.
There were a lot of positives to our tour, the crew was fantastic, they were helpful, knowledgeable, and even managed to keep the nautical puns to a minimum. They also give you a nice overview of the history of the area.
The boat was lovely, it was nice to be out on the water in a sail boat. It is a modern boat only 20 some years old, but fits the feel of the area. The only negative was that due to the current health crisis we were not allowed below deck.
The views were nice but
There were a lot of positives to our tour, the crew was fantastic, they were helpful, knowledgeable, and even managed to keep the nautical puns to a minimum. They also give you a nice overview of the history of the area.
The boat was lovely, it was nice to be out on the water in a sail boat. It is a modern boat only 20 some years old, but fits the feel of the area. The only negative was that due to the current health crisis we were not allowed below deck.
The views were nice but
Courtney A.
Jul 10, 2020
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We scheduled this as a spur of the moment kind of adventure. The ship appears very well maintained. The crew were extremely nice. We got to help hoist the sails and steer the boat. The crew entertained with information about the Yorktown area and the ship. Had a lot of fun and now I have the sailing bug.
Michelle L.
Nov 07, 2019
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My husband and I have done their sunset cruises twice, once as a couple October 2018, and more recently with my parents. AMAZING!
It is well worth the money it is a great experience. The first time was a perfect 68° fall evening absolutely beautiful and could not of been better or at least I thought.
The second time I was with my parents like I said I believe it was May 2019. We only had 2 nights in Williamsburg. First night cruise was canceled because of weather which we thought was a little odd cents really ended up getting a little rain that night. They offered to either a refund or to book
It is well worth the money it is a great experience. The first time was a perfect 68° fall evening absolutely beautiful and could not of been better or at least I thought.
The second time I was with my parents like I said I believe it was May 2019. We only had 2 nights in Williamsburg. First night cruise was canceled because of weather which we thought was a little odd cents really ended up getting a little rain that night. They offered to either a refund or to book
Cheryl M.
Aug 13, 2019
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My gf and I took the afternoon sail. Thankfully, while warm, there was a wonderful breeze. Our hosts were friendly and the historical information was interesting. I even learned some information I was unaware of about an ancestral home in Yorktown. I've spent much of my life on the water on workboats, but this was a first time on a sailboat. Quite magical.Involving the passengers in lifting the sails was fun. The quiet time which allowed us to wander was my favorite. I enjoyed just standing at the rail and chatting with my significant. I was reminded of my time spent on the water, and how
Claude P.
Aug 12, 2019
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Queenp M.
Aug 01, 2019
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Victor H.
Jul 08, 2019
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We took the sunset cruise on July 6 2019, we had a nice time and the captain and crew were knowledgeable and let the passengers help raise the sails. Only 2 stars because they way overbook this sail. We were 47 people on a boat that could comfortably seat around 30 people
We really could not move freely we were stuck in the back
We ordered a dinner box with our payment but that was not on board as the crew didn't pick them up prior to departure so we were offered other items like hot dogs or veggie burgers which were ok but had we known we would have made other dinner plans
This would have
We really could not move freely we were stuck in the back
We ordered a dinner box with our payment but that was not on board as the crew didn't pick them up prior to departure so we were offered other items like hot dogs or veggie burgers which were ok but had we known we would have made other dinner plans
This would have
Paul J.
Jun 17, 2019
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I always thought going out on a ship and sailing was beyond my price range, but with this ship, I was proven wrong. The crew and captain were excellent and made the trip extremely enjoyable. Getting the passengers involved was a great experience that my knee wouldn't let me try my hand at this time, but next trip, I definitely will. I am very pleased with the experience, and it not expensive like I thought. I will definitely book again next time I come down to Williamsburg, which is rather frequent. A huge thank you to the captain and crew (Christian and Emily(?)) for the new experience, and
Anna G.
Jul 18, 2018
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We signed up for the pirate cruise - thinking a pirate theme would be something the kids would LOVE. while the crew is dressed the part, they are quiet and seem to be put off with questions about the shoreline, yorktown, or pirate history. I had expected a bit more enthusiasm and energy from the crew but it seemed like they were phoning it in and couldn't wait until we were back.
The captain was gruff and answered questions begrudgingly. It certainly wasn't worth the money spent.
The captain was gruff and answered questions begrudgingly. It certainly wasn't worth the money spent.
Tania V.
Jun 19, 2016
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Went today and took advantage of the sunset sailing on the Alliance. It's a 105' foot schooner. The crew allowed anyone to pull up the sails and help out. The crew that consisted of 2 young ladies were very skilled and have been sailing for quite a few years. The boat also had a galley. They took cash and card with a $10 minimum. You could get beer,soda , water, or chips. The sunset was awesome! Definitely go with ur honey, bring a blankie and get a seat on top of the flat rectangular boxes next to the entrance. You'll love it!!
