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.

These are the pictures you want on your camera roll. 📸☀️ We’re sailing Saturday, Sunday and Monday for Labor Day weekend...
09/04/2026

These are the pictures you want on your camera roll. 📸☀️ We’re sailing Saturday, Sunday and Monday for Labor Day weekend! Call for reservations (410) 263-0002.

Fall weekends in Annapolis are for getting out on the water and getting in on the fun. ⚓️The kids may be leading the adv...
08/27/2026

Fall weekends in Annapolis are for getting out on the water and getting in on the fun. ⚓️

The kids may be leading the adventure, but grown-ups are definitely invited to play along.

We’re sailing weekends in through October 25. 🍂🏴‍☠️

Grab your crew and come aboard!

Beautiful weekend of pirating - now sailing Saturdays and Sundays through October 25th. 🌤️ 🍁
08/23/2026

Beautiful weekend of pirating - now sailing Saturdays and Sundays through October 25th. 🌤️ 🍁

08/18/2026

✨ The KPop Demon Hunters need a crew! 🎶

Kids will set sail on a Pirate Adventure aboard the Sea Gypsy 🏴‍☠️, then head back on land to meet KPop Demon Hunters characters in our party room. 💜

If the movie and music have been on repeat in your house, your kids won’t want to miss this one!

🎟️ Character cruises have a way of selling out.
🔗 Get tickets: https://www.chesapeakepirates.com/pirates-and-princesses-cruise/

Next up: Moana & Rapunzel • October 18th 👑🌺

08/14/2026

Come squeeze in one more summer adventure for with us 🏴‍☠️

08/12/2026

Apparently no one told these pirates summer is winding down. 💃🏴‍☠️☀️
We’re dancing our way through the last couple weeks of weekday adventures, and there’s still plenty of summer left to squeeze in an adventure with us. ⚓️
Weekday trips continue through August 21. But don’t worry, we’re not packing up the treasure just yet. 🗺️✨ Weekend adventures continue into the fall. 🍂

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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