sailboat charter virginia

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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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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.

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Sail Chesapeake Bay

• Location Guide

Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

NEXT PUBLIC SAIL IS SUNDAY, NOVEMBER 2 AT 5PM - 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! (opens in new window)

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