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Chesapeake Bay Sailboat Adventure near Williamsburg, VA in Yorktown

A Chesapeake Bay sailing is a lovely activity if you're in the Virginia, Maryland, or Washington, DC area. The bay is usually calm and an excursion on the water can help you “stop and smell the roses,” so to speak, even if only for a few hours.

We were in the Williamsburg, Virginia area for a weekend trip , and ending our three-day vacation with an afternoon sail was the perfect way to close it out.

Disclosure: There are affiliate links in this post, which means we may earn a small commission if you click the link and proceed with a purchase,  at no cost to you . We truly only recommend hotels, products, and services we personally use. As Amazon Associates, we earn from qualifying purchases.

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Chesapeake Bay Sailing from Yorktown

One of the cool things about the area is how historic it is. European settlers came over from the other side of the Atlantic in boats. And hundreds of years later we're still able to enjoy those same waters to sail around the coast. Amazing!

sailboat cruise yorktown va

Thankfully, Yorktown Sailing Charters makes that possible.

sailboat cruise yorktown va

Yorktown Sailing Charters and the Schooner Alliance

This beautiful ship does three distinct sailing excursions in Virginia. No matter the sailing you choose, you may see dolphins and osprey and even have the opportunity to help with the sails and steering.

1. Yorktown Sightseeing Day Sail

We did this excursion and it was fabulous. It's about 1.75 hours and leaves during the day. (Our sailing was at 2:00pm.)

2. Yorktown Scenic Sunset Sail

Sail the Chesapeake Bay for up to 2 hours and see the sunset from a unique vantage point: on the water. Time is dependent upon the setting sun, of course, but expect to leave the pier at 5:00pm or 5:30pm, depending on the day you book.

3. Pirate Adventure Sail Yorktown

1.5 hours (great for children): Memorial Day through Labor Day (end of May through the beginning of September) at 10:30am.

Learn to tie knots, steer the ship, and fire the canon. Pirate tattoos are available for children too. (And hopefully, kids of all ages if the adults want some.)

All of these sailings are incredibly affordable at under $40 per person.

There's a maximum of 30 people on the ship during normal sail times.

The ship is available for private charters as well, for special birthday celebrations and events, like if you want to get married on the ship. (And we know a great wedding photographer: Mikkel !)

Learning about the History of Yorktown as you Sail around the Chesapeake Bay

The staff on the ship are very knowledgeable about the area and coastline. They narrate the trip and you're able to listen (if you like) or tune it out and escape to your own little world, feeling the breeze on you and enjoying the fresh air.

The scenery won't blow your mind but it is quite lovely and calming. Sailing in a bay isn't often about the scenery but the journey and experience.

sailboat cruise yorktown va

The Chesapeake Bay Sailing Experience

Being aboard a sailing ship is a real treat. (Whether it's an excursion or something like an overnight schooner trip with Maine Windjammer Cruises .)

The ship's owners, Greg and Laura Lohse, captain the sailboat. They're friendly and welcoming and have been sailing together for over 30 years.

When you're aboard the schooner you have the option to help out or simply sit back and relax. Dan and I loved helping with the sails and being of service! And otherwise, we enjoyed life together aboard the ship and some beer that was available for purchase.

sailboat cruise yorktown va

About the Schooner Alliance

We LOVED the name that was chosen by the ship's owners, Greg and Laura, and the meaning behind it.

The schooner Alliance was named for the pivotal relationship between the French and Americans that allowed the United States to win its independence in the American Revolutionary War in the 1780s.

There's also an alliance between Greg and Laura, married and sailing partners. Such a cute double entendre!

The Alliance hull was built in 1995 in Palm Coast, Florida, and she was outfitted in Maine in 1996. Her deck length is 80 feet and her overall length is 105 feet. A “schooner” is a type of sailboat that denotes the types of sails on the ship.

She used to sail the Maine coast as a member of the Maine Windjammer fleet . (The ship can actually fit 12 passengers overnight.)

Her former name was the “Kathyrn B.” during her life in New England. Greg and Laura purchased her in 2005.

Even then and now, the Alliance remains in Caribbean waters during winter. (Shouldn't we all, really?)

sailboat cruise yorktown va

⛵️ Not con vinced to book a sail on Alliance? Check out what other guests are saying on TripAdvisor !

Practical Information for Yorktown Alliance

A few things to note to make your sailing experience extra smooth.

  • There is a restroom on board but they're asking guests to refrain from using it and use the facilities at Riverwalk Landing before boarding, due to COVID safety measures.
  • Bring cash: you can buy beverages onboard and it's nice to tip the crew .
  • Sunglasses and sunscreen are a must!
  • Wear comfortable clothes. This isn't a fancy boat – it's joyfully low-key, comfy, and fun. (NO platform or heeled shoes!)
  • Bring a lightweight cardigan or jacket if you like – it may get windy.

sailboat cruise yorktown va

Driving to Yorktown from Williamsburg, Virginia

Yorktown has a lovely area on the York River, called Riverwalk Landing. This is where the sailing excursions head out to the Chesapeake Bay, shortly after leaving the harbor and heading south.

We left about 30 to 45 minutes time to arrive at the harbor, find parking, and check in from brunch at Williamsburg Winery that morning.

Parking in the area is easy, thanks to a parking garage. However, it can get very congested with traffic even on a random weekend in October, when we were there. So just have some patience and leave yourself time so you don't have to rush, just in case.

sailboat cruise yorktown va

Riverwalk Landing is a fun place to explore too. It's not too big but has a few places to get ice cream, drinks, restaurants, and some shops. They often have events on the lawn as well, like a farmers market.

sailboat cruise yorktown va

Heading to the east coast? Also read:

  • River Cruises in the US: Start Here to Plan Your American River Adventure
  • United States Cruise Ports Map and Information
  • 23 Ways to Be a More Eco-Conscious Cruiser Before, During + After a Cruise

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Mikkel and Dan Woodruff co-own and operate Sometimes Sailing. Through their cruising expertise, they bring the best travel ideas on the world's waterways to their audience along with packing tips, budgeting advice, and seasonal deals. They have been featured on many of the best cruise podcasts, including DCL Duo and the Joy of Cruising. Their articles are nationally syndicated and have appeared on AP Wire various times.

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Yorktown, Va., to be Featured on Princess’ 2024 Schedule, First Major Oceangoing Cruise Line to Visit Virginia’s Historic Triangle

America’s earliest settlements, revolutionary war sites and charming small towns provide guests with unique experiences ashore.

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For the first time ever, Princess Cruises will call at Yorktown, Va. and Virginia’s Historic Triangle, as part of a series of custom-curated itineraries in summer 2024 that will highlight opportunities to experience Colonial Williamsburg and Jamestown in addition to visiting the historic seaside town.

Princess Cruises is planning five day-long calls – three via Island Princess (2,200 guests/900 crew) and two via Emerald Princess (3,080 guests/1,200 crew) – that will result in a significant economic impact to the region, which has played an important role in American history.

Additional details, including specific sailing dates, itineraries and shore excursions, are expected to be announced in the coming weeks.

“Princess is already well known for our unique itineraries that appeal to our guests who gravitate toward interesting historical and cultural opportunities and Yorktown is perfectly in tune with that philosophy, offering not only a glimpse at the Revolutionary War but also dining, shopping and activity options with wide-ranging appeal. It’s a win-win for everyone,” said John Padgett, president of Princess Cruises.

Padgett added that the new itineraries are even more significant as interest builds ahead of events and festivities across Virginia to commemorate the 250 th anniversaries of the Revolutionary War and the Declaration of Independence.

“Our community is rooted in history and it is an important part of our visitor mix. We are honored that Princess Cruises sees the value in bringing their customers to Yorktown,” said Kristi Olsen-Hayes, Director, York County Economic & Tourism Development. “Additional visitors coming to our area via the cruise line would contribute to the region’s economy, benefiting retail, restaurants, and regional attractions, as well as generating revenue for both the Commonwealth and multiple local governments.”

As the first major cruise line to call on the region, Princess understands and appreciates the significant role it plays in boosting area tourism and, as it does with other homeport and port of call communities, the company will work with local tour operators to showcase the attributes of this fascinating historical region while benefiting local residents.

“We couldn’t be more excited about this incredible opportunity to add this truly unforgettable destination experience to our already impressive array of itineraries,” said Padgett. “As a native Virginian myself, I can attest that an itinerary that offers the chance to visit Colonial Williamsburg, Jamestown and Yorktown promises to be a most welcome addition for our guests, providing them memorable vacation experiences that they can’t find anywhere else.”

Yorktown offers 300 years of history from revolutionary battlefields to 18th Century homes. Picturesque streets provide the backdrop for art galleries, antique and specialty shops, while attractions like the Watermen’s Museum offer hands-on programs and exhibits for all ages. Entertainment, including Fifes and Drums performances, abounds, and visitors can stroll along the scenic riverwalk lined with charming restaurants and shops that offer a view of the York River.

Sure to be a popular shore excursion, a visit to Colonial Williamsburg will allow guests to discover why this was the capital of Virginia and the largest, most prosperous American colony. Men and women from all walks of life strolled these streets, and Princess guests will follow in their footsteps as they re-trace history They’ll also explore dozens of original buildings, homes, and shops reconstructed on 301 acres – most on their original foundations. Rare animal breeds, historic trades, and lovingly restored gardens add layers of authenticity to the Colonial Williamsburg experience. Guests will feel as if they’ve traveled back in time.

Guests opting to visit Jamestown, just a short, 30-minute motorcoach ride from the port, will be captivated by the history behind the original site of the first permanent English settlement in North America and the story of the role of the three cultures - European, North American and African - that came together to lay the foundation for a uniquely American form of democratic government, language, free enterprise and society.

Princess Cruises sails to more than 330 incredible destinations around the world. More information is available through a professional travel advisor, by calling 1-800-PRINCESS (1-800-774-6237) or by visiting the company’s website at www.princess.com .

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Schooner Alliance Sailing - Yorktown Sailing Charters

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  • Yorktown - Things to Do    
  • Yorktown Sailing Charters

Booked this sunset cruise for my husband’s birthday, very nice deck crew/captain. offered beer wine... read more

sailboat cruise yorktown va

My wife and I took the Sunset Sail and it was beautiful! Got some great pictures. Crew was funny... read more

sailboat cruise yorktown va

Schooner Alliance Sailing

While on vacation my family and I decided to try something new. We have been to the historic triangle area for the last 20 years and were running out of new experiences. We took the 2hr sunset cruise and it was a very pleasurable experience. It had rained heavily just before our boarding time but luckily it stopped just in time. As a result we were able to see beautiful rainbows and cloud formations. The crew offered info on the ship and surrounding points of interest. My husband and children helped with raising the sails. My parents also joined us. There were maybe a dozen folks on board from teenager to senior citizens and there was something for everyone to experience. You could be engaged in conversation or just enjoy the peacefulness of the York River. And the sunset was truly spectacular.

sailboat cruise yorktown va

Went on the sunset cruise ($35 per person); it was supposed to be a 2 hour cruise, but we were only out for an hour and 15 minutes. Don't know why the time was cut short; the weather was fine. Older man, owner of the ship, sailed the ship, while a young high-school girl and a 20/30ish age male served as crew. The crew hoisted the sails with volunteers from the passengers. Points of interest were pointed out along with the way by the young female crew member. Overpriced beer/wine/sodas/snacks were sold on board. Limited places to sit on the ship. The crew members did not present a good image for a sunset cruise, on which most of the passengers were neatly dressed and freshly showered. The two crew members had on filthy t-shirts, and looked very unkept. A clean shirt, a comb, and a washcloth to freshen up would have done them wonders. I realize they are hosting 3 cruises a day; but they are also responsible for projecting an image that represents the business. There was also no music on board the ship. It would have been nice to listen to some Jimmy Buffett or island music while cruising at sunset. For $35 per person, it could have been a lot better!

Out of all the things to do in Yorktown, I would have to rate a cruise on the Alliance as my favorite! We boarded the ship from the dock in the center of the River Walk, although it should be noted that credit cards are not accepted, so bring cash. After boarding the ship we received a thorough airplane style safety briefing on the ship and then we set sail. Turning towards the George P Coleman bridge, we got an opportunity to hoist the sails (a lot of fun but more work than you might think!). The ships crew, including first mate "JM" (John Michael) and second mate Julianna took the time to explain everything from why a schooner is a schooner to what each sail was for and how to raise them. During the cruise they explained more about the ship, the York river, and information on the local area. It was very relaxing and enjoyable sailing the river under sail power only. We were able to observe the US Coast Guard conducting training drills both at the dock and on the river in the area. Once under way, the crew opened the galley, where water, ice cream, beer and other refreshments were available. Don't forget the camera on this trip as the are a lot of great photo opportunities. The only sad part of the entire trip was that the two hours went by way too fast. The rest of Yorktown is pretty average, but the Alliance is a cut above.

sailboat cruise yorktown va

This as a great experience. We took a morning cruise and were able to see 2 Navy ships pass under the bridge, with the bridge opening horizontally. We were told this is the only bridge in the country that opens like that. The three member crew were very friendly and knowledgable. The ride was smooth. The price was reasonable. Will definately do it again if in the area. A must do if in the Yorktown area.

In June,18 members of the Werner Reunion visited Historic Yorktown,VA. Some went on a tour of Yorktown aboard Segways which was a new experience for all. Yorktown has a great website with details on everything. We had made reservations for the 3pm. sail for the 18 of us on the Alliance. They list 3 sailing times but you should check ahead. It was a 2 hour sail on the Alliance,a 3 masted sailing vessel,down the York river and back. The 2 young crew members were very knowledgeable and efficient. We returned to Historic Powhatan via the Colonial Parkway which is a beautiful drive. . ,

We booked an evening cruse on the James River. The captain cut it short by about an hour. Not sure why the weather seemed okay. The captain is a little weird-he went on and on about not wanting a party boat-belive me you could not party here if you tried. They do sell some snacks and some cans of beer/ wine I believe. It was actually kind of boring. The captain has some young kids who live on the boat and serve as crew also. They told us they live aboard with no air, no TV etc... They seemed odd also. They hung out after we docked for tips-probably the only money they see. They told you a little about the history but if you have been anywhere in the area visiting you already know the most basic stuff they told us. I would not recommend this attraction. The captains wife captains the other boat they own called the Serenity which is also in the area. This was just not a fun, interesting or exciting trip and the crew is just too weird.

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Yorktown Sailing Cruises

Yorktown Sailing Cruises

With the Yorktown Sailing Charters sailing cruise, you'll have the chance to experience travel on the high seas as it was over 300 years ago - aboard a tall ship! You'll sail aboard the Schooner Alliance, much like the ship Capt. John Smith used when trading with the Powhatan Indians.

The journey will take you past the Yorktown Battlefield, Victory Monument, the banks of the York river and more as you experience the culture and history of America while simultaneously seeing the beautiful sites of the Williamsburg area. If you are lucky, the crew will let you lend a hand at setting sail. The Sunset Tour lasts about two hours. It is very family- friendly and great for all ages. 

The Alliance is a ship has seen many different waters in her lifetime. Built in Florida in 1995, she was a charter vessel in Maine and cruised around the Caribbean Islands before being purchased by the Yorktown Sailing Charters in 2005. Now, she is a daily charter vessel that cruises the York River. Aboard, there are four queen staterooms with their own bathrooms, two double cabins, and a Captain's cabin.

A perfect fit in combination with the other historic activities in Williamsburg and great as an addition to any Williamsburg VA vacation , experience the history of sailing with the Yorktown Sailing Charters.You may even see other fun things to do in Williamsburg  while on the trip.

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  • What type of parking do you have? There is parking on Ballard St. across from the Post Office.
  • Approximately how long is the cruise? It is approximately two hours long
  • What lake or river does the sailboat cruise on? It sails the York River.
  • How many passengers does the boat hold? 49 passengers
  • What is the dress code? Casual - you may want to dress warm because it can get cold on the water

Yorktown Sailing Charters

Private Charters

Enjoy the splendor of a sunset sail.

You will return to the by-gone days of old sailing ships when you step aboard the Schooners Serenity or Alliance II . Sit and relax or lend a hand at setting sail.

We can customize your charter to fit your needs. We offer a variety of catering and beverage services for private events. Call us to discuss charter options.

Contact us today to book your York River sailing charter and Yorktown sunset cruises at 888-316-6422 .

The perfect venue for that special event! Great for family gatherings or office parties!

a person sitting on a dock next to a body of water

Private Charter Rates 2023:

Schooner Alliance II  can carry up to 42 guests for private charters.

1.5 hour private charter day sail: $2,000 (Saturdays & Sundays $2,100)

2 hour private charter sunset sail: $2,500 (Saturdays & Sundays $2,600)

A contract and advance payment are required for private charters or large groups.

  • Only an hour away from the Richmond metropolitan area, and 25 minutes from Colonial Williamsburg.
  • Free parking within 1 block of the dock.
  • Street address for GPS: 425 Water Street, Yorktown, VA 23690
  • Mailing address: York River Cruises, P.O. Box 238, Yorktown, VA 23690
  • Call 888-316-6422 for charter information

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COMMENTS

  1. Yorktown Sailing Charters

    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!

  2. THE 5 BEST Yorktown Boat Rides & Cruises (Updated 2024)

    2023. 1. Yorktown Sailing Charters. 1,795. Boat Tours. Great service lots fun nice boat very clean and crew is awesome nice trip great view lots good history information an... 2. Best Williamsburg Tours. 42.

  3. Yorktown Sailing Charters

    Oct 2020. A well organized schooner sailing experience. About thirty guests and a crew of four travelled two hours on the York River. Covid-19 presentations and USCG Safety Briefings were appropriate. The challenge for this vendor is an unusually large number of uncontrolled variables. Our experience was a sun-free, sunset cruise, a sailing ...

  4. Yorktown, VA Sailing on the York River

    Sail the York River on the Schooner Serenity. Offering day and sunset sails, private charters and sightseeing cruises out of historic Yorktown, Virginia. Set Sail for a by-gone Era! New This Year ... Street address for GPS: 425 Water Street, Yorktown, VA 23690. Mailing address: Yorktown Sailing Charters P.O. Box 238 Yorktown, VA 23690 ...

  5. All You Need to Know BEFORE You Go (with Photos)

    About. 2 hour cruises on the York River aboard the Schooner Alliance. Sailing from Historic Yorktown's Riverwalk Landing April to November. Yorktown, Virginia. Contact.

  6. YORKTOWN SAILING CHARTERS

    Specialties: 2 hour sightseeing cruises aboard Yorktown's Schooner Alliance. Established in 1995. The Lohse's began their daysail business in Cape Charles on VA's Eastern Shore in 1995 with their 45' pocket schooner Delight. In 2000 they upgraded to the 65' schooner Serenity to continue the daysail business in Cape Charles. In 2005 they upgrade again and purchased the 105' schooner Kathryn B ...

  7. Schooner Alliance, Yorktown Sailing Charters

    Schooner Alliance, Yorktown Sailing Charters, Yorktown, Virginia. 3,290 likes · 5 talking about this · 3,603 were here. Sailing cruises on the York River aboard the Schooner Alliance

  8. Chesapeake Bay Sailboat Adventure near Williamsburg, VA in Yorktown

    Sail aboard the Schooner Alliance with Yorktown Sailing Charters off the York River into the #ChesapeakeBay, in a historic Virginia. #VisitWilliamsburg #VisitVirginia ... VA in Yorktown. Published on June 26, 2022 January 10, 2023 Updated on January 10, 2023. 12 shares. Flipboard; Share; ... Sometimes Sailing is a cruise-focused website by Dan ...

  9. Schooner Alliance, Yorktown Sailing Charters

    Schooner Alliance, Yorktown Sailing Charters, Yorktown. 3,063 likes · 39 talking about this · 3,334 were here. Sailing cruises on the York River aboard... Facebook. Email or phone: Password: Forgot account? Home. Reviews. Photos. Videos. ... Yorktown, VA, VA 23690. Get Directions (888) 316-6422.

  10. About Us

    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 Serenity. On the Historic Yorktown cruises you will sail past the Yorktown Battlefield where our country won its independence, and relive ...

  11. - Williamsburg Charter Sails Home

    August 15, 2023. Sailing with Dolphins - What an awesome day with Captain Bill of Williamsburg Charter Sails. Our family enjoyed sailing the York River as my dad did growing up. It was a beautiful day to share and honor memories of time spent with him while on the water. Seeing the dolphins and sailing alongside of them made the day.

  12. Two Princess Cruises Ships to Call at Historic Yorktown

    Ties to Revolutionary War. Two Princess Cruises ships will include five-day-long port calls to Yorktown on their itineraries in summer 2024, with three visits by the 92,000 gross ton, 2,200-guest ...

  13. Scenic Sunset Cruise / Sail Yorktown

    Yorktown Sailing Charters: Scenic Sunset Cruise / Sail Yorktown - See 1,795 traveler reviews, 475 candid photos, and great deals for Yorktown, VA, at Tripadvisor. Skip to main content. Discover. ... 425 Water Street, Yorktown, VA 23690. Open today: 9:00 AM - 9:00 PM. Save. Review Highlights

  14. TOP 10 BEST Boat Tours in Yorktown, VA

    Top 10 Best Boat Tours in Yorktown, VA - March 2024 - Yelp - Yorktown Sailing Charters, Native Island Sailing, Bay Fly Fishing, Bay Country Kayaking, Great White Water Sports, Electrified Marina

  15. Yorktown, Va., to be Featured on Princess' 2024 ...

    For the first time ever, Princess Cruises will call at Yorktown, Va. and Virginia's Historic Triangle, as part of a series of custom-curated itineraries in summer 2024 that will highlight opportunities to experience Colonial Williamsburg and Jamestown in addition to visiting the historic seaside town.

  16. Private Sunset Cruise Yorktown VA

    From $55. Schooner Serenity. 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. Book Now.

  17. Sailboat Rentals in Yorktown, VA

    Yorktown, VA is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The sailboat rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 5 charters are currently available with or without captain, lined up in the Yorktown's marinas, waiting for their guests.

  18. Schooner Alliance Sailing

    Yorktown Sailing Charters: Schooner Alliance Sailing - See 1,795 traveler reviews, 475 candid photos, and great deals for Yorktown, VA, at Tripadvisor.

  19. Yorktown Sailing Cruises

    425 Water St Yorktown, VA 23690. Yorktown Sailing Cruises is no longer available. This activity is no longer available. Top related activities are listed below: Let's Go Sail Virginia. Let's Go Sail the York River in Gloucester Point, Virginia. Williamsburg 3 Hour Sailing Cruise. Dead Of Night Tour in Williamsburg. Williamsburg Segway Tours.

  20. Private Charters

    Street address for GPS: 425 Water Street, Yorktown, VA 23690. Mailing address: York River Cruises, P.O. Box 238, Yorktown, VA 23690. Call 888-316-6422 for charter information. Experience exclusive adventures with Private Charters by Yorktown Sailing Charters. Tailor your sailing experience for a memorable voyage. Call us to book!

  21. Dinner Cruise Yorktown, VA 23690

    Top 10 Best Dinner Cruise in Yorktown, VA 23690 - March 2024 - Yelp - Yorktown Sailing Charters, City Cruises Norfolk, Carrie B Showboat, American Rover, Rudee Tours, Hampton Yacht Club, Powhatan Plantation Resort, Dockside Seafood & Fishing Center, Sea Hooker Charters