Pirate Adventures on the Chesapeake

Pirate Adventures on the Chesapeake "On the pirate ship Sea Gypsy we always find the treasure, we always defeat that stinky pirate, and the children always walk away with incredible stories!"
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Sail away in search of sunken treasure aboard our children's pirate cruise in the Annapolis Harbor. Perfect for family fun, field trips and birthday parties Pirate Adventures is an interactive experience on the high seas. Fire our famous water cannons, face painting and dress up, and a treasure hunt on the water make for an unforgettable adventure that your kids will remember for years to come.

06/14/2026

Summer doesn’t wait.

Good thing we’re now sailing 7 days a week.

Come aboard the Sea Gypsy for imagination, adventure, and the kind of afternoon your kids will talk about all summer long.

One more thing to look forward to this summer.Starting NOW, Pirate Adventures sails daily.Weekdays or weekends, we’ll be...
06/05/2026

One more thing to look forward to this summer.
Starting NOW, Pirate Adventures sails daily.
Weekdays or weekends, we’ll be ready when you are.

Image credit Laura's Focus Photography

Summer planning doesn’t have to be complicated.Pirate Adventures presale tickets make it easy to have something fun alre...
06/01/2026

Summer planning doesn’t have to be complicated.

Pirate Adventures presale tickets make it easy to have something fun already waiting for your family.

✔ Buy presale tickets now ✔ Pick your date later
https://www.chesapeakepirates.com/pre-sale-tickets/

Ariel is coming aboard for our Pirate Princess Cruise on June 6… and she invited some friends. 🧜‍♀️Join us aboard the Se...
05/28/2026

Ariel is coming aboard for our Pirate Princess Cruise on June 6… and she invited some friends. 🧜‍♀️

Join us aboard the Sea Gypsy for pirate adventure on the water, treasure hunting, and swashbuckling fun.

Then head ashore to our indoor party room where Ariel, Belle, and Cinderella will be waiting for a magical princess meet & greet filled with photos, smiles, and royal fun.

✨ Costumes encouraged
June 6
https://www.chesapeakepirates.com/pirates-and-princesses-cruise/
Swipe to see who Ariel invited ➡️

Memorial Day weekend brought more rain boots than sunglasses this year ☔️But there’s something pretty magical about watc...
05/25/2026

Memorial Day weekend brought more rain boots than sunglasses this year ☔️

But there’s something pretty magical about watching kids show up ready for adventure anyway with zero concern for the forecast.

A good reminder that childhood magic doesn’t wait for perfect weather, and summer 2026 is here! 😎

Finally. A weekend for the water ☀️If Pirate Adventures has been on your list, this might be your sign.Come sail with us...
05/15/2026

Finally. A weekend for the water ☀️

If Pirate Adventures has been on your list, this might be your sign.

Come sail with us this weekend ⚓

Put a Pirate Adventure in your back pocket.Presale tickets let you pick your date later and use them anytime.Right now i...
05/11/2026

Put a Pirate Adventure in your back pocket.

Presale tickets let you pick your date later and use them anytime.

Right now is the lowest price of the season.

Get your presale tickets at the link in bio.

05/08/2026

Last call for Mother’s Day.

Moms and grandmoms sail free this Sunday, May 11.

Sailings are nearly full.

Call now to reserve your spot.

Address

311 Third Street
Annapolis, MD
21403

Opening Hours

Monday 8:30am - 6:30pm
Tuesday 8:30am - 6:30pm
Wednesday 8:30am - 6:30pm
Thursday 8:30am - 6:30pm
Friday 8:30am - 6:30pm
Saturday 8:30am - 6:30pm
Sunday 8:30am - 6:30pm

Telephone

+14102630002

Website

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