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!"
(490)

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.

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]

No Ren Fest tickets? No problem.This weekend may be Pirate Adventure Weekend at the Maryland Renaissance Festival, but h...
09/11/2025

No Ren Fest tickets? No problem.
This weekend may be Pirate Adventure Weekend at the Maryland Renaissance Festival, but here in Annapolis we’ve got pirate adventures every weekend through October 26! 🚢🏴‍☠️
💦 Fire the water cannons.
⚓️ Hunt for treasure.
👑 Make memories your family will treasure.
🎟️ Book now before our season slips away!

09/05/2025

✨ Last Call for Princess Magic! ✨

We have just a few tickets left for the Pirate Princess Cruise – Fair Winds & Fairy Tales this Sunday, September 7 at 9:30 AM.

Set sail for pirate adventure, then meet Ariel & Tinkerbell after the cruise for a morning your little pirates and princesses will never forget.

Don’t wait—these last spots will disappear like fairy dust!

Photo dump of the perfect Labor Day Weekend, thank you weather gods and all the mates that joined us this weekend!  Brin...
09/02/2025

Photo dump of the perfect Labor Day Weekend, thank you weather gods and all the mates that joined us this weekend! Bring on the beautiful fall weather! 🍁 Catch us sailing fall weekends through 10/26.

08/31/2025

Gorgeous Labor Day Weekend underway! ⛅⚓🦀
Still some tickets left for tomorrow afternoon - come find the treasure with us!

08/29/2025

Whose excited for Labor Day Weekend!?!? Weather looks AMAZING and we still have a few spots left each day.
📞 Call (410) 263-0002 now to reserve before we sell out!

👑⚓ Step into the story! Our Pirate Princess Cruise is sailing Sunday, September 7.Set sail for a Pirate Adventure and th...
08/27/2025

👑⚓ Step into the story! Our Pirate Princess Cruise is sailing Sunday, September 7.
Set sail for a Pirate Adventure and then meet Ariel & Tinkerbell after the cruise.
Tickets are limited — reserve your spot today!

🍁 Fall into High Seas Birthday Fun! Sailing weekends through Oct. 26. Dates filling fast — book now!
08/22/2025

🍁 Fall into High Seas Birthday Fun! Sailing weekends through Oct. 26. Dates filling fast — book now!

⚓ Celebrate Labor Day Weekend on the High Seas! ⚓Set sail with Pirate Adventures this Labor Day Weekend (August 30 – Sep...
08/21/2025

⚓ Celebrate Labor Day Weekend on the High Seas! ⚓

Set sail with Pirate Adventures this Labor Day Weekend (August 30 – September 1) and enjoy an adventure the whole family will love.

As a special thank you, First Responders, Police, Fire, and Teaching professionals receive 10% off tickets with valid ID at check-in.

It’s the perfect way to wrap up summer with sunshine and a salute to our local heroes.

📞 Call (410) 263-0002 to reserve your spot.

Hard to say goodbye to our college crew but also so much FUN! Our crew works hard, plays hard and makes the pirate magic...
08/18/2025

Hard to say goodbye to our college crew but also so much FUN! Our crew works hard, plays hard and makes the pirate magic happen for so many kids. We couldn’t be more grateful for all their hard work this summer! Next up, fall crew!

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

Alerts

Be the first to know and let us send you an email when Pirate Adventures on the Chesapeake posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Pirate Adventures on the Chesapeake:

Share

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.