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Annapolis Boat Ride For Kids: Our Review of Pirate Adventures on the Chesapeake

When thinking of Annapolis, many people think of sailing and fishing. It’s no surprise, as Maryland’s capital has 520 miles of coastline! Hanging out on the water is one of the fun ways to spend the day in Annapolis with kids.

On a recent visit to Annapolis, we were able to experience a fun family-friendly Annapolis boat ride with Pirate Adventures on the Chesapeake .

Disclosure: Some of the links below are affiliate links, meaning, at no additional cost to you, we may receive a commission if you click through and make a purchase.

Boats Rides for Kids in Annapolis: Pirate Adventures on the Chesapeake

Sailing with the Pirate Adventures on the Chesapeake provides an enjoyable way to spend some time on the Annapolis Harbor. A family-owned and operated attraction since 2003, they obviously enjoy working with kids. The pirate crew puts on a great show, and their excitement rubs off on the new recruits.

Pirate Adventures Location and Parking

The Sea Gypsy sets sail at the end of Third Street in the Eastport neighborhood of Annapolis. Limited parking is available in their lot. Additional parking can be found at the Annapolis City Marina Parking Lot. If you park in this lot, remember to present your parking ticket at Pirate Adventures to receive a discounted parking rate!

Sailing Times and Cost of a Pirate Adventure Cruise

This pirate ship sets sails 7 days a week from mid-April through Labor Day, and weekends through the end of October. Sailing times vary based on the season, so visit their website for the most updated information. Reservations are highly recommended, as they have limited capacity on the ship.

A ticket to board the Sea Gypsy is $22/person (at time of publication). Discounted tickets are offered for pirates 2 years of age and under. Click here for the most updated ticket prices. They also offer discounted tickets on specific sailing times. You can learn more about those discounts here.

Pirate Adventures also offers group rates for field trips and birthday parties. They have a spacious, beautifully decorated, dedicated area for parties. It is a perfect event for your next celebration!

What to Expect on Your Pirate Adventure Cruise

A lot of pirate fun!

But seriously, your kids will be entertained from start to finish on a Pirate Adventure cruise. The crew works non-stop to engage children, all while staying in pirate character.

After check-in, children transform into mermaids or pirate. Mermaid tails and tutus or pirate vests and hats are some of the options for kids to choose from the large chests full of dress-up clothing. 

After your child is dressed up in their mermaid or pirate garb, they will receive a tattoo. Don’t worry; it’s not permanent! Kids choose which design they’d like, and the expert pirate tattoo artists paint it on their forearm, cheek, or even forehead.

Once everyone is ready to go, kids get a crash course on what it takes to be a pirate, including using pirate language like “aye-aye” and “huzzah!”. Once they are deemed sea-worthy, the new pirate recruits are led the pirate ship Sea Gypsy.

Aboard the ship, the typical pirate activities take place. Kids shoot water cannons at rival pirates, search the map for the X, and find the treasure. Of course, there are a few mishaps and antics along the way, making the trip even more enjoyable for everyone on board. 

The entire experience lasts about 1 hour and 45 minutes. The time flies by quickly! The pirates and their mates provide so much fun and entertainment throughout the trip.

Our Thoughts on Pirates Adventures on the Chesapeake

Ultimately, the kids found both the Pirate Adventures on the Chesapeake to be tons of fun!

They loved playing pirate and mermaid while laughing at the antics of Boots and Captain Spike on the Pirate Adventures cruise.

If you have enough time on your next visit to Annapolis with kids we also recommend visiting Kent Narrows and Ferry Point Park Beach. There is a lot to do in the area that’s fun for everyone.

Read It Now, Pin It For Later!

Family-Friendly Annapolis Boat Rides - Pirates Adventures on the Chesapeake and Family Fishing Adventures are two fun ways to spend time on the water! - Where the Wild Kids Wander - #familytravel #annapolis #maryland

Lauren
Lauren

Lauren is the visionary behind Where the Wild Kids Wander. She is a travel enthusiast who lives outside of Philadelphia. For more than a decade, she's been hitting the road, exploring the nooks and crannies of the United States alongside her family. Her passions include visiting big cities and small towns and trekking through nature's trails. She loves sharing those adventures with fellow travelers.