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Williamsburg, VA

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Bay Country Kayaking

5.0 (3 reviews)
Open • 9:00 am - 7:30 pm

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Yorktown Sailing Charters

Yorktown Sailing Charters

4.0(67 reviews)
12.1 mi
Locally owned & operated
Certified professionals

Our family had a fantastic sail on the Alliance II. The schooner was in great shape with plenty of…read moreseating, and the crew were knowledgeable. Captain and crew made everyone welcome and went above beyond to assist guests. The 2 hour sunset sail was beautiful and it's a great location to view from the water. I also want to thank Yorktown Charters for accommodating a change in our cruise date. We originally had scheduled a cruise in July but had to cancel at the last minute due to an unexpected illness. Without asking, The company converted our reservation to a gift certificate that we were able to use for a future booking. So grateful we were able to reschedule for this weekend. Class A organization!

Road the Schooner Alliance on a hot summer day with no wind so we moved by motor, but at multiple…read morepoints it felt like we weren't moving and were baking on the boat. If you go on a hot day, sit towards the front of the boat because you'll get any breeze that gets mustered up by the boat's movement. I'm not a boat person, and if it wasn't so hot out, I think I would have liked it better. The crew were so friendly and informative about how the boat works and they fired a cannon, which was neat. The drinks they offered were cold and went well with the boat riding. The chairs they have are plastic folding chairs, which ended up being more comfortable than expected.

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Yorktown Sailing Charters
Yorktown Sailing Charters - Daily Sailing Charters, historic adventures on the York River, Yorktown, VA

Daily Sailing Charters, historic adventures on the York River, Yorktown, VA

Yorktown Sailing Charters

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Miss Hampton - The Miss Hampton II returning to port after a 3 hour cruise.

Miss Hampton

4.4(16 reviews)
28.3 mi

A fantastic tour. We arrived early for the tour and Rachel…read morechecked us in. We had a short wait before the captain said we could board. Rachel made us feel comfortable. We talked with her while we waited for others to check in. Captain Charlie let us board on time. No surprises or delays. Bev and I used the walkers to get down the ramp. Captain Charlie with the whole crew greeted every passenger at the bottom of the ramp. They helped us over the step onto the tour boat. Adam assisted the captain in getting us on our way. He wore his life vest as he was out front on the boat. We were indoors. Bev and I sat down on a table right in the front. Most passengers went upstairs to the next level. We did not think we could manage so many steps so we sat in the room we came in. Hudson also assisted throughout the event. He answered many questions we had about the trip. Captain Charlie's voice came over the speakers and shared many facts about the area. We were looking left right and front. Captain Charlie is so friendly and naturally funny. Bev and I enjoyed his commentary. Bev had questions about specific things as she lived in this area for 23 years. Hudson answered all of them. He is very knowledgeable about the area. Adam took our order for drinks so we did not have to go upstairs to the bar. He kindly brought them to us. We also asked for snacks. Cookies and chips to go with our drinks. I gave him my credit card and he returned with everything. Adam checked on us often. He is so friendly, kind and has a great sense of humor. Bev and Adam would banter back and forth. Both have a quick wit. We were taking everything in. It was such a beautiful sunny day with a slight breeze coming across the Chesapeake Bay. On the way back to the dock we saw so many dolphins. They were swimming and jumping out of the water. So beautiful and exciting. I'm sure the joy in my heart was seen through the smile in my eyes. Once we docked Rachel was right there to welcome us home. Time flew by so fast with so much to see. Rachel was joined by Captain Charlie, Adam and Hudson to see us safely to shore. We loved this trip don't just take our word come check it out for yourself. Thank you Willie n Bev.

The boat was clean and comfortable and the commentary was interesting. Several years ago I…read morepurchased the Hampton Sea to Stars combination ticket. We were saving, the cruise, the best for last. The first Miss Hampton operator retired, so there was a three-year delay from when I purchased to when we could do the cruise. We appreciated the new owners who were gracious and honored our Sea to Stars Combination ticket. The staff was friendly and helpful. It was a very hot day. The staff recommended that we would probably be the most comfortable at the bow of the boat where there was a cool spray and a nice breeze.

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Miss Hampton - Miss Hampton is great cruise.

Miss Hampton is great cruise.

Miss Hampton - Front of Miss Hampton II boat

Front of Miss Hampton II boat

Miss Hampton

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Jamestown Discovery - Jamestown Haunted River Cruise 8:45pm tour

Jamestown Discovery

4.8(5 reviews)
19.9 mi

We had a wonderful experience on the Jamestown discovery boat tour. Captain Corey and First made…read moreWilliam made our ride very smooth. The seats were comfortable, and there was a nice little tray that folded down where we could set our beverages and our phones. Captain Corey was a wealth of information and he made the experience very interactive. It was incredible to get to see history from this different angle. It was obvious that Captain Corey loves what he does. And is very natural on the water. He worked very hard to help us to see wildlife as well. We even got to see a bald eagle! I learned a lot during that one hour ride, and would certainly recommend as well as come back again! If you want to learn more about the Jamestown settlement and the island, this is definitely worth booking a ride.

Great sunset tour on the James River! Our party of 10 friends had a really enjoyable sunset tour…read morewith Captain Corey and William this past week. The boat is clean with comfortable seat cushions and pop-up tables in each row for drinks and snacks, which you may bring on board. We enjoyed the wine and baked goods we brought with us. The ride is mostly pretty smooth since the boat is a pontoon boat. We had a short period of time with some rocking while watching the sun set, but it didn't last long. Captain Corey's commentary about the James River and Jamestown Island was fun and interesting. We saw wildlife such as eagles and great blue herons. When the boat was out on the James River, we saw the Jamestown-Surry Ferry. We then went close to the recreated ships at Jamestown Settlement. The sunset on the James is spectacular. Though we had some clouds, it was still lovely. As the sun sets, they play music, which adds to your enjoyment. The tour lasted an hour. I highly recommend for a couple, a family, and a group of friends!

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Jamestown Discovery - Jamestown Haunted River Cruise 8:45pm tour

Jamestown Haunted River Cruise 8:45pm tour

Jamestown Discovery - Jamestown Haunted River Cruise 8:45pm

Jamestown Haunted River Cruise 8:45pm

Jamestown Discovery - Jamestown Haunted River Cruise

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Jamestown Haunted River Cruise

Captain Dan's Around the Island Tours

Captain Dan's Around the Island Tours

4.9(102 reviews)
71.5 mi

Our boat tour with Captain Dan's Around the Island Tours was absolutely terrific!! This was easily…read moreTHE highlight of our day on Chincoteague. Captain Dan took us all around Chincoteague and Assateague, including up into the shallow marshes where the smaller boat could get us wonderfully close to the wildlife and scenery. We saw bald eagles, the Chincoteague ponies, Assateague Lighthouse, and some absolutely beautiful parts of the islands that you just can't appreciate from the road. You can normally see dolphins, but they didn't make an appearance for us. What really made the trip special, though, was Captain Dan himself. He was incredibly knowledgeable, personable, and clearly loves the area. We must have asked him a billion questions about everything under the sun--wildlife, fisheries, the ponies, the islands, local history, the marshes, even county sewage issues -- and he happily answered every one of them in depth. It felt much more like spending a couple of hours exploring Chincoteague with a very knowledgeable local (he's 7th generation on Chincoteague!!) friend than taking a standard tourist boat ride. The two hours flew by, and we came away knowing that we had seen and learned so much more about Chincoteague and Assateague than we ever had before. We can't recommend Captain Dan highly enough. If you're visiting Chincoteague, put this tour on your must-do list!

EXCEPTIONAL TOUR-- I took the 1/2 pony 1/2 dolphin tour!…read moreCapitain Doug was experienced and had a need for speed so hold on! what a thrilling ride!!! ;) First we saw the wild ponies -- the capitain found all their hiding places and we were up close and personal with the ponies. Then we sped out to the ocean to see the dolphins! The ocean is chopping so hold on!! Again, he found the dolphins near the shore and gave us every angle to get a great picture! On the way back he spotted a young pelican and we stopped to check it out! Yes, you need to take this tour!

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Captain Dan's Around the Island Tours
Captain Dan's Around the Island Tours
Captain Dan's Around the Island Tours

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Smith Island Cruises-Tyler - Smith Island Cruises - Crisfield

Smith Island Cruises-Tyler

4.7(6 reviews)
47.7 mi

Bottom Line. Reliable and friendly transportation to Ewell on Smith Island…read more The brackish water of the Chesapeake Bay runs through my veins and I love the heritage and culture of the region. I've traveled the Eastern Shore and the Western Shore and I've now finally made it to the in between of Smith Island, in part thanks to Smith Island Cruises. My husband and I took the ferry from Crisfield to the village of Ewell on Smith Island. The ferry is a two-deck passenger ferry that probably holds around 100 people but on Labor Day weekend I think there were only about 30 aboard. Passengers are welcome to bring their luggage aboard including coolers. You can bring bikes too but there is a charge. Smith Island is dry so if you're hoping to have a drinky drink then discretely bring your own. The ferry trip is advertised to take about 45 minutes but depending on conditions, such as wind, it could take longer. During the cruise the captain pointed out some landmarks and provided a little history which was a nice touch. Overall the trip was scenic and I'm glad I had my birdnoculars in tow. The ferry is no frills. It offers a safe passage, friendly service and two bathrooms. Online ordering of tickets is easy. You can also reserve a golf cart and Smith Island cake at the same time. If departing from Crisfield then you pick up your tickets (wristband) at the Captain Tyler Motel before hand and then they'll direct you to free parking near the B pier at the marina. It was a very simple and organized process. Once on Smith Island we got a delicious lunch at the Bayside Inn and then went to the nearby Cultural center where we enjoyed the exhibits and got a walking tour map for the town. For our short 2.5 hours on the town we found waking, versus gold cart riding or biking, to be adequate. Shout out to the employee on board in the first mate/hospitality role - he was friendly and welcoming.

Took this trip from Point Lookout Captain Jack was the best!…read moreHe gave a great tour as he narrated the trip to Smith Island and gave some education along the way. We Ebenezer had a little quiz on the way back on facts that we were given on the way over. Very entertaining . The mate was really good too... he passed out sliced watermelon on the way back. We were kind of hot and a little tired and that was so nice! The boat does have bathrooms. The online tickets are very easy.

Photos
Smith Island Cruises-Tyler - The ferry in Crisfield prior to boarding.

The ferry in Crisfield prior to boarding.

Smith Island Cruises-Tyler - In Crisfield tickets (wristband) can be picked up at the Captain Tyler Motel.

In Crisfield tickets (wristband) can be picked up at the Captain Tyler Motel.

Smith Island Cruises-Tyler - View from the ferry ride of an old hunting lodge that local birds now call home.

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View from the ferry ride of an old hunting lodge that local birds now call home.

Bay Country Kayaking - rafting - Updated October 2026

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