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Sailboats for sale in Virginia

• Sailboat Listings
• United States
• Catalina (41)
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21 listings found

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2011 Laser 14 Williamsburg, Virginia, United States

1983 Challenger 60 | Magic Carpet Norfolk, Virginia, United States

1977 Islander 32 | Concession Saluda, Virginia, United States

2003 Compac 20 Williamsburg, Virginia, United States

1987 Island Packet 38 | Chasing Summer Norfolk, Virginia, United States

1975 Amf 14 Aldie, Virginia, United States

1975 Amf 14 | NA Aldie, Virginia, United States

2008 Precision 18.5 Midlothian, Virginia, United States

1979 Whitby 37 | Sea Gypsy Hampton, Virginia, United States

1985 Alberg 37 | Zipporah Deltaville, Virginia, United States

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1968 Cal 20 Cardinal, Virginia, United States

1982 Stevens 47 Hampton, Virginia, United States

1979 Westerly 33 | Persistence Newport News, Virginia, United States

1986 Catalina 34 | ImPluse Yorktown, Virginia, United States

1977 Columbia 27 | Euphoria Lottsburg, Virginia, United States

1983 Hans Christian 33 | Bijou Hampton, Virginia, United States

1973 Cal 46 | Defiant Deltaville, Virginia, United States

1969 Cheoy Lee 35 | Traveller I Offers Welcomed! Deltaville, Virginia, United States

2004 Catalina 32 | Flying Cloud Kilmarnock, Virginia, United States

1969 Cheoy Lee 36 | Traveller Deltaville, Virginia, United States

1990 Freedom 45 | Jade Moon Urbanna, Virginia, United States

Sail Yorktown

Yorktown's sailing tours: yorktown, va, explore yorktown's sailing charters.

• our most popular!
• User All ages
• Hour Glass 1 hour and 30 minutes
• Sailboat Schooner Alliance II

Schooner Alliance II: Yorktown Sightseeing Day Sail

Enjoy a daytime cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Immerse yourself in 300 years of history and enjoy the village streets and paths overlooking the York River before you board the ship. Book online!

• Hour Glass 2 hours

Schooner Alliance II: Yorktown Scenic Sunset Sail

Take a scenic sunset cruise aboard the Tall Ship Alliance II on the York River from the Riverwalk Landing Pier. Come aboard and enjoy the evening views of the York River while enjoying a beverage from our ships’ galley.

Yorktown Pirate Ship Adventure Sail

Bring the kids to Captain Mayhem’s School of Piracy and watch them set the sails, steer the schooner, and learn sailor skills! This sail is our kid-friendly cruise, recommended for kids 10 and under. Older kids may prefer Sightseeing Day sail.

July 4th Fireworks Cruise

What could be more patriotic than watching the July 4th Fireworks from a tall ship at Yorktown’s waterfront? This trip departs after the sunset sail and returns after the fireworks.

Explore Our Yorktown Sailing Charters

Yorktown Sailing Charters | Williamsburg Sailing

Set Sail for a By-Gone Era with Yorktown Sailing Charters

Step back into history when you join the crew of the Yorktown Schooner Alliance or Schooner Serenity. 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 sailing’s Golden Age as you cruise past the Victory Monument and Battlefield where our country won its independence. Book your Yorktown cruises online today!

For those who love history, yearn for romance, or have dreamed of a true sailing adventure,

Your Yorktown Ship has just come in!

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.

Whether you’re looking for things to do in Williamsburg, VA or searching among the best sailing charters on the Chesapeake Bay, your journey stops with us.

Yorktown Cruises & Sailing Specials

Special events are welcome as we are pleased to offer private sailing charters for weddings, corporate cruises, our own exciting pirate cruises and more. Among the popular pirate cruises you will watch as the kids raise the sails, learn sailors skills and truly experience what it was like years ago aboard a schooner! Catering services and beverages for purchase are available options for your convenience.

For the ultimate enjoyment of a day of sailing come join Yorktown Sailing Charters. After boarding the Schooner Alliance II (48 passengers max) or Schooner Serenity (6 passengers max) you will understand why so many satisfied customers have raved about our sailing cruises for years! We look forward to introducing you to the history, romance and beauty found in and around our boats.

Yorktown Cruise Ships & Sailing Charters Events

Thank you for checking out our website. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. If you have questions about any of our tours or how you can book a tour, give us a call today at 888-316-6422 or send an email . We look forward to hearing from you and taking you on your next sailing tour!

What Our Customers Have To Say! ★★★★★

Delightful Sail!

A wonderful afternoon with friends sailing out of Yorktown. It was a delightful 90 minutes on the water aboard a two-masted schooner.

Great Experience!

It was our first time visiting Williamsburg Yorktown and Jamestown and the sightseeing sail was definitely something we wanted to do and we were not disappointed. The Captain and crew were very friendly and we learned a lot of history of the area. Overall it was a wonderful time and very relaxing afternoon. Would definitely recommend!

Yorktown Sailing Charter!

We had a great time. Wish there would have been a little more wind. The commentator was very well versed in his local history.

We had a blast!

We thoroughly enjoyed our sunset cruise. The crew was excellent and we especially enjoyed the history lesson. We highly recommend Yorktown Sailing Charters.

It was very informative and fun. Would do it again.it was not crowded like other tours. The crew was very friendly. You definitely get what you pay for.

Chesapeake Sail Club

Sail the chesapeake bay for the 2024 season, boad creek, deltaville, virginia.

Our home port, Broad Creek, at the mouth of the Rappahannock River, means great destinations on the river and bay are within an easy morning or afternoon sail.

Explore the numerous deep water creeks off the Rappahannock – drop your anchor or berth at the available facilities and explore local villages. Favorites include Urbanna, Topping and Irvington.

Set course for a secluded creek and enjoy the natural beauty and wildlife that only the Chesapeake Bay area can offer, favorites include the Corrotoman and Antipoison.

Sailing Chesapeake Bay from Broad Creek, heading either north or south there are numerous bays, rivers and waterfront towns to visit. Favorites include Fleet’s and Little Bays, Great Wicomoco River area and Mobjack Bay.

Sailing east, across the bay, to the eastern shore, you will find quaint and welcoming towns such as Onancock and Cape Charles.

Solomons, MD and Portsmouth/Norfolk, VA are within a few days of sailing from our Rappahannock home port, when your schedule allows.

What Members are Saying

My daughter and I had a great day sailing yesterday. The friends we took with us had a great day as well. Read more

The CSC Fleet – Our Sailing Yachts

With the start of the 2023 sailing season, club members can sail either Bianca , a Tartan 34 keel/centerboard sloop or Ula, a Freedom 32 – your choice each time you reserve sailing time. Both yachts are well equipped, comfortable cruisers.

NEXT PUBLIC SAIL IS WEDNESDAY, SEPTEMBER 18 AT 6PM- SEE YOU ON BOARD!

American Rover Sailing Cruises

Sunset cruises, norfolk harbor tours, & private boat charters in norfolk, virginia, setting sail from downtown norfolk since 1986.

• Hour Glass 2 hours
• Clock Varies

Two-Hour Norfolk Harbor Cruise

See the sights on this daytime cruise, our most popular for children and families! You can lend a hand setting the sails, take a turn at the helm, or simply sit back and enjoy the cruise as the captain points out the highlights of the harbor!

Two-Hour Sunset Cruise

Set sail on this fun and romantic evening cruise! The Sunset Cruise is the perfect way for adults, couples, groups of friends, and colleagues on a company outing to spend an evening.

Sail the Elizabeth River & the Port of Virginia

Set sail with the friendly and experienced crew of this 120-passenger sailing schooner. We offer daytime and sunset Norfolk Harbor cruises under sail on the smooth waters of the Elizabeth River and the Port of Virginia. Help hoist the sails, take a turn at the helm, or just relax as the captain points out the sights on this historic Norfolk Harbor tour. Sunset cruises feature live entertainment.

This elegant ship with her distinctive red sails is Coast Guard inspected for safety. Comfortable seating is available on the shaded upper deck and in our air-conditioned below-deck area with ship store, bar, and restrooms. Our sails and charter boats in Virginia have been popular for families, weddings , field trips, group outings , and company parties since 1986. Cruises depart from the Waterside Marina in Downtown Norfolk. Come aboard and sail with us!

Read Reviews of Our Incredible Crew & Boat Tours in Norfolk, VA

I imagine a lot depends on how the weather is, but we lucked out. It was calm (didn't help the sailing portion I suppose), and the skies were clear. Not too hot either. We got to experience a perfect sunset, and even got a bonus moonrise out of the deal! The ship's Captain was great and explained everything as we were sailing. As it got to sunset time, a musician entertained the ship by walking around and taking requests. It was fun all around and everyone seemed to enjoy it.

I have been on this cruise four times now. It is great! The crew is friendly and knowledgeable. The boat is extremely clean and very comfortable. There are two very clean bathrooms onboard. They sell adult drinks, sodas, and snacks. Also, there is a musician that walks around singing and playing the guitar. He plays fun sing-along songs by a variety of artists. This cruise is my favorite thing to do in Norfolk!!! I will be back for a fifth time later this summer!!

This was probably a highlight for me, I absolutely loved it and told my husband I couldn’t wait to go again. The captain gave a wonderful tour and for couples wanting to experience a romantic evening, this is very romantic, watching the sunset was just beautiful. I highly recommend it, you won't be sorry!

This was a great way to entertain the family. We enjoyed drinks, musician and the narrative from the captain. The night was warm with a slight breeze and the sunset even cooperated. It was a peaceful and relaxing time.

This was a perfect activity for a beautiful day! The crew was very friendly and the Captain gave a narrative of what we were seeing. It was really impressive to see them set the sails. A great way to see the harbor!

Perfect, affordable outing for my family! 2 of our teenagers was away for the weekend which left us with our 10 & 2-year-olds! So peaceful and relaxing for ALL!

Would highly recommend, great commentary, friendly staff, bar and snacks available and length is just right

Check out our other cruise options in Norfolk and Virginia Beach!

Atlantic explorer whale & dolphin watching, victory rover naval base cruises, atlantic scout dolphin watching, naval station bus tours.

Discover the Sailing Life

at Northern Virginia Sailing School

When are We Open?

After closing for the season at the end of October 2023, we will open again from April 2024 through October 2024.

Where are We?

Take a breath of fresh air at one of Northern Virginia’s most popular parks while cruising in the sunshine!  While you are here,

be sure to take a walk down Leesylvania State Park’s path along the shore to read about the park history and understand why our sailing school has such an iconic and historical significance here on the Potomac River.

Northern Virginia Sailing School is nestled at the marina in Leesylvania State Park, directly on the lower Potomac River in Woodbridge, Virginia.  We are less than an hour from Washington, DC, easily accessible from I-95.

What Do We Offer?

The sailing school has been operating at this location since 2010, graduating countless sailors in American Sailing certifications . There are sailboats available to rent for certified sailors, captains available to take out your group, and specialized classes for all levels of sailing expertise.  We even offer classes for new sailboat owners on their own vessels.  All sails are scheduled by appointment, using an online scheduler which is fast, flexible, and convenient.

What Do We Sail?

Our most popular sailboat, used for introductory lessons and rentals, are Catalina 22s with outboard motors.  Catalina 22s have tough fiberglass hulls, masthead sloop (with a main and head sail), and swing keels.  Considered a “Daysailer,” they are resilient and safe teaching boats requiring lots of hands-on rigging and steering.  In 1995, Catalina 22s were even entered into the American Sailing Hall of Fame. It continues in popularity to this day as the first boat of many new sailors.  Once the Catalina 22 is mastered, it is more intuitive to make the jump to bigger, live-aboard sailboats. We also have other similar-style popular sailboats brands that we use interchangeably for a varied sailing education, such as the Hunter and the San Juan.  

Our more advanced courses are held on a much larger Hunter 31 with full navigation equipment, inboard diesel motor, and all the gear needed to experience cruising on a live-aboard sailboat.

Who Are We?

We have a small crew of top-notch instructors with varied experience all over the world.  Our focus in education is quality, as we limit class sizes for optimum teaching.  Each of our instructors are committed to safety.  Click here to meet them!

What Sets Us Apart?

At Northern Virginia Sailing School, you can expect your American Sailing classes to be entirely on the water.  You can expect to have more time sailing, with a very quick motor past the breakers to the river.  You can expect to learn at your own pace and schedule, with classes available throughout the week and weekend for you to sign up as you are able.  

How to get started?

If you cannot wait to get started and are new to sailing, you can sign up for a Try Sail class , book a Cruise , or sign up for the American Sailing 101 course, Basic Keel Boat .  If you have sailed before and are certified, we offer Rentals on our Catalina 22s and advanced American Sailing certification courses such as:

ASA 102: Keelboat Sailing 2 ASA 103: Basic Coastal Cruising ASA 104: Bareboat Cruising

We simply offer quality sailing with fantastic instruction.   Check out our reviews and facebook page – they speak for themselves:

Join Our Facebook 5.0 Star Rating

Google reviews 4.9 star rating, yelp reviews 5.0 star rating,  our sailing community.

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Fully Crewed Sailing Yacht Charters

Chesapeake bay sailing at its best.

Book your private fully crewed luxury sailing charter on a catamaran or monohull in the Chesapeake Bay and Hampton Roads. Perfect for couples or small groups.

Hampton Roads Premier Luxury Sailing Experience

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Screen Rant

Below deck sailing yacht season 5 trailer leaves fans disappointed with gary king’s involvement.

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Below Deck Sailing Yacht season 5’s trailer has finally arrived, and with Captain Glenn Shephard’s crew including First Officer Gary King, fans are disappointed in the show’s return . While Below Deck viewers have been impatiently awaiting news about Below Deck Sailing Yacht season 5 for over a year, the trailer has finally been released, and has many concerned about what the season is going to look like. While the trailer reveals the return of some familiar faces, the storylines that appear to be part of the season left viewers feeling uneasy. After Gary’s sexual misconduct allegations, his involvement seems overwhelming.

In the Below Deck Sailing Yacht season 5 trailer, the crew’s chartering guests around Ibiza in a new sailing adventure. With Gary showing up early in the trailer after Daisy Kelliher makes her grand entrance, things get dicey quickly. “That’s right, we have a f****** job and I’m not carrying this f****** season on my own you f****** prick,” Daisy shouts at Gary in one moment of the trailer as he lays in his bed, looking dismayed. The rest of the trailer shows the genuine chaos of the season, featuring Gary heavily much to the surprise of Below Deck viewers .

What Gary’s Involvement In Below Deck Sailing Yacht Season 5 Means

He’s part of the show more than ever.

Throughout the Below Deck Sailing Yacht season 5 trailer, it was clear that Gary will be a focal point of the exterior team’s story. Being shown on the deck with some of the exterior team, pushing Deckhands to their limits and critiquing their work, Gary’s presence on the sailing yacht may be odd during Below Deck Sailing Yacht season 5 . While he appears to be getting along with Daisy , he may not even have her in his corner by the end of the charter season. His heavy involvement in the trailer may not indicate the same throughout the whole season.

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Although Gary has been a part of Below Deck Sailing Yacht since the early days of the series, seeing him as a member of the crew after his sexual misconduct allegations came to light is tough. While Bravo filmed Below Deck Sailing Yacht season 5 before the allegations were revealed, they came to light during the filming of the season and it appears that the network didn’t choose to remove Gary from later episodes or take action at all. Though it remains to be seen if production did anything about Gary , it’s disappointing to some to see him on screen.

Our Take On The Below Deck Sailing Yacht Season 5 Trailer

It could be chaotic fun, but gary leaves a stain on the show.

Although the trailer for Below Deck Sailing Yacht season 5 makes it seem like one of the most exciting, dramatic seasons of the series we’ve ever seen, the mess may not be worth it if Gary’s involved. By ignoring the sexual misconduct allegations lodged against Gary and leaving him on the series, seemingly without explanation, Bravo is allowing it to seem like what he may have done is okay. Though nothing has been proven, taking no action on Below Deck Sailing Yacht could be a misstep that may taint the entire season of the sailing spin-off for once excited viewers.

Below Deck Sailing Yacht premieres Monday, October 7 at 9 p.m. EDT on Bravo.

Source: Below Deck /Instagram

Below Deck Sailing Yacht

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Below Deck Sailing Yacht is a spin-off of the Below Deck reality television series. Premiering on Bravo, the show follows the life of a Yacht crew as they attempt to navigate a busy Charter season in which many customers make use of a 177-foot sailing yacht. Over the first three seasons, the yacht has been to Greece, Croatia, and Spain.

Danni Warren

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Your First Look at Below Deck Sailing Yacht Season 5

Chase Lemacks Says Goodbye to the Below Deck Sailing Yacht Crew

Gary King to Chase Lemacks: "I've Never Worked with a Deckhand Like You"

Your First Look at the Below Deck Sailing Yacht Season 4 Reunion

There’s Trouble in Paradise for the Throuple Onboard

Daisy Kelliher Tells Gary King They Need to Stop Flirting

Gary King and Chase Lemacks Show Off Their New Speedos

Alex Propson and Mads Herrera Get a Surprise Personal Training Session

Ileisha Dell Is Short on Time as She Prepares a 10-Course Dinner

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Gary King and Daisy Kelliher Escort the Guests on a French Shore Excursion

Chef Ileisha Dell Describes Herself as “Pretty Loyal” in Relationships

Glenn Shephard

Daisy Kelliher

Cloyce Martin

Davide Morosi

Keith Allen

Emma Crouch

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first blood yanks

With about nine knots of wind from the northeast, the race committee blew the first starting horn just fifteen minutes late, at 11:45 am. After nearly an hour and a half of intense competition, it was Newhouse and Wilmot’s “Yonder”, from the New York Yacht Club, who took the win ahead of Douglas Rastrello’s “Good to go”, also racing under the U.S. flag representing Newport Harbor YC. Third place in this first race of the World Championship went to a Spanish team, Luis Albert’s “Patakin” from the Real Club Náutico de Palma. Results .

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