Boat Rides For Kids | Pirate Adventure on the Chesapeake

Jun 6, 2017 | Fun Things To Do With Kids in MD, DC, and VA

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Find Family Fun at Pirate Adventures

Set sail in search of fun with us and experience a Pirate Adventure with your family aboard the pirate ship Sea Gypsy in the Annapolis Harbor.

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Boat Rides for Kids in Annapolis

Looking for summer fun?  Come to Annapolis and find boat rides for kids of all kinds!  It’s nice to walk around city dock and look at all the boats out in the harbor. But on a hot June summer day, it’s tough to be landlocked when there are so many opportunities to get out on the water!

Interactive Boat Rides for Kids

Though the history of Annapolis is quite interesting. It is summertime, give the kids a little break from the facts and let their imaginative minds run freely! Kick back and enjoy a cruise out on the bay as the crew entertains your child  for an hour and a half on the Sea Gypsy. Pirate Adventures on the Chesapeake gets the family out on the water the fun way. The pirate ship cruises down Ego Alley drinking pirate Pete’s grog while yelling Argggh and Ahoy to our mates at Pussers dining.  The cruise includes facepainting and dress-up as well as a search for sunken treasure and a live water cannon battle!


A couple piers over, you’ll find our friend the Sea Dragon. Family Fishing Adventures is Maryland’s newest child & family attraction. The Sea Dragon is fully equip with rods for the whole family and stocked with crab pots, nets, life jackets and more. It’s totally hassle free fishing adventure that is geared towards a kid friendly experience. Though, it is just as much fun for the adults to see that excitement in their kids eyes while they reel in their first rockfish straight from the Bay!

Hoist the Sails

Our neighbors across the harbor  have two 74-foot wooden schooners. The Woodwind and Woodwind II set sail from the Annapolis Waterfront Hotel up to four times a day for a two hour sail. With kids on board, the crew takes an interactive approach by educating them about sailing and pointing out wildlife in the Chesapeake bay.


Harbor Cruises

If your looking for a cruise a little shorter and more informational, check out Watermark cruises. The one  we yell Argggg in passing quite often is the Harbor Queen. The Harbor queen is a 40-minute narrated cruise of the Annapolis Harbor about the U.S naval academy and  history of Annapolis. The harbor queen is a larger boat but Watermark also offers rides on Miss Anne, which is a much smaller vessel. It travels down into Spa Creek teaching you about the history from the 17th century to present day time. Though its not exactly catered to entertain children, kids ride for only $6!


Paddle and Float

If you would rather rent a kayak, canoe or paddle board, our third street neighbors, Annapolis Canoe and Kayak, offers rentals for the whole family!



We hope to see you on the water with your kids in Annapolis this summer, either aboad our kid-friendly pirate ship or waving Ahoy from other boat rides for kids in Annapolis!