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.

11/10/2025

Whether it was your first time or your tenth, we want to thank all the mates who came out and sailed with us this season.

That’s a wrap on 2025 — the crew is getting a well-deserved rest before we return for Season #24 on April 17, 2026.

If you’re already dreaming of next year’s adventures, holiday gift certificates are now on sale at chesapeakepirates.com.

The Sea Gypsy will be waiting when spring set's sail! 🍃🌸

10/25/2025

🎃⚓️ The pumpkin patch came to us!

The Great Annapolis Pumpkins have arrived — and one of them looks right at home aboard the Sea Gypsy. 🏴‍☠️

It’s our final weekend to sail, and Annapolis is all dressed up for Halloween! 🍂☀️
Climb aboard for one last adventure, then stroll downtown to see the incredible pumpkin carvings on display.

🍁 Blue Skies. Pirate Tides. Fall Vibes.

🍂 One last weekend to sail the Sea Gypsy! Tickets are available for 10/25 and 10/26⚓️Climb aboard and soak up the magic ...
10/22/2025

🍂 One last weekend to sail the Sea Gypsy! Tickets are available for 10/25 and 10/26⚓️

Climb aboard and soak up the magic before we dock for the season 🏴‍☠️

It’s been a beautiful fall on the bay, and we can’t wait to celebrate the final voyage with our crew — that means you! ☀️

🎟️ Book your family’s adventure today and make one more memory on the Chesapeake before we say farewell to 2025.

10/19/2025

🍂 One weekend left to sail!
Don’t miss your crew’s last chance to fire the water cannons, hunt for treasure, and soak up the sunshine aboard the Sea Gypsy. ☀️⚓️

It’s been another beautiful fall weekend in Annapolis, let’s end the season with a splash! 💦🏴‍☠️
🎟️ Book your adventure before we dock for the year!

09/19/2025

🏴‍☠️ Happy International Talk Like A Pirate Day ☠️

Think you can do better? 📹 Share a video of your kids best pirate talk (feed or stories) and tag us []. One lucky buccaneer will win a $50 gift card to sail with us this fall.

🗓️ Entries close 9/20 — winner announced 9/21.

09/16/2025

🎂 “Happy Birthday” hits different on the high seas…
Fall into High Seas Birthday Fun aboard our pirate ship! 🍂⚓
We’re sailing weekends through October 26 — don’t let your child’s special day sail away.
📅 Reserve your fall party today: [link]

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

https://lnk.bio/pirateadventures

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Sail Away in Search of Fun Today!

Welcome to Pirate Adventures on the Chesapeake, a place where children come to experience the magic of sailing away in search of buried treasure. Come aboard our pirate ship and get caught up in this real life adventure and be amazed as our crew taps into the wonder of a child’s imagination. This is not a typical pirate cruise, before you know it your child will be painted with a curly mustache or a beautiful mermaid, dressed up as a pirate and marching off to the ship. Once aboard the young pirates will learn the rules at sea aboard their pirate ship and read a treasure map to find our sunken treasure. A message in a bottle floats by and the children discover that Pirate Pete, the smelliest most rotten pirate on the seven seas is lurking nearby and he has something our brave crew needs. Off we go into battle with our famous water cannons! Will the crew defeat Pirate Pete and find the sunken treasure? 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! Pirate Adventures on the Chesapeake is conveniently located between Baltimore and Washington DC in the historic port town of Annapolis. Operating since 2003 you will find that our great program, our caring, high energy staff and our commitment to your child’s satisfaction make Pirate Adventures an outstanding choice for families spending the day together, children birthday parties, and school field trips.