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.

Looking for one more adventure before school starts?Washington Parent just named Pirate Adventures one of the top last-m...
08/05/2025

Looking for one more adventure before school starts?
Washington Parent just named Pirate Adventures one of the top last-minute getaways for DC families—and we couldn’t agree more.

Looking for a quick family trip before school starts? Explore the best last-minute weekend getaways near DC, including Baltimore, Shenandoah, Colonial Beach, Annapolis and Philadelphia. Fun, food and adventure await.

08/03/2025

☀️ August just arrived—and there’s still time for one more epic adventure before the school year starts.

Celebrate 23 seasons of pirate fun with our Anniversary Special, and give your crew a day they’ll never forget. Treasure hunts, water cannon battles, and Blackbeard's Boneyard are calling your name!
Book Now: https://www.chesapeakepirates.com/anniversary-specials/

If you’re a pirate and you know it 👏👏
07/28/2025

If you’re a pirate and you know it 👏👏

07/26/2025

⚓️ This is your weekend adventure, pirate-style.
Let your kids dress up, chase treasure, and blast the water cannons while summer’s still in full swing.

🎟️ Book your voyage before it’s too late — we’re sailing all weekend!

✨ This is what treasure looks like.All earned on the high seas.⚓ Your little pirate’s big adventure is just one booking ...
07/23/2025

✨ This is what treasure looks like.
All earned on the high seas.

⚓ Your little pirate’s big adventure is just one booking away.
🎟️ Book now — treasure (and fun!) awaits.

07/22/2025

$5 Day never disappoints—thank you to everyone who came out to be part of the madness, the magic, and the memories.

From the first customer in line to the last pirate stepping off the ship, this day continues to be one of our favorite traditions.

07/20/2025
07/17/2025

Some things never change…

Whether it’s 2023 or 2025, one thing’s for sure: the energy is real, the adventure is epic, and the tickets are still just $5.

📅 Mark your calendar for Monday, July 21—no reservations, just first come, first served fun.
👉 Find out how things work in the comments.

07/16/2025

We’ll never get tired of this video—or $5 Day!

The biggest day of the season returns Monday, July 21, and it’s just as wild, fun, and unforgettable as ever.

Tickets are only $5, but remember—no reservations are taken. It’s first come, first served at the, and we always draw a crowd. DOORS OPEN AT 8:00 AM.

Make sure you know how it works before you come down to get tickets:
👉 https://www.chesapeakepirates.com/pirate-adventures-5-day/

07/14/2025

CHEERS TO 23 YEARS!
Raise a cup of pirate grog and celebrate with us — this Sunday only, tickets are just $23 at 5pm in honor of our 23rd anniversary.

⚓ Make a toast to memories your crew will treasure forever.
🎟️ Spots are limited — snag your tickets before they sail away!
https://www.chesapeakepirates.com/anniversary-specials/

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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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.