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Monday 9am - 7pm Tuesday 9am - 7pm Wednesday 9am - 7pm Thursday 9am - 7pm Friday 8:30am - 7pm Saturday 9am - 7pm Sunday 9am - 7pm

Pirate Adventures on the Chesapeake

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United States
Annapolis, MD
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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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.

10/28/2024

Oh hey! Happy Halloween! 🧜🏽‍♀️ 🏴‍☠️ 🎃

10/21/2024

That’s a wrap on SEASON 22! If you know, you know. It was a good one. Old crew, new crew and we ended it with . Thank you to EVERY wide eyed pirate and mermaid who walked through our doors ready to - see you in the spring! 🏴‍☠️⚓️

08/25/2024

08/18/2024

Last week for Anniversary Special Tickets - $22 this Thursday!

Join us to celebrate our 22nd anniversary with $22 tickets once a week. A different sailing time each week will be posted by Sunday afternoons.

08/05/2024

Rum-N-Around we won! 🏴‍☠️ 🏴‍☠️ 🏴‍☠️

08/03/2024

Celebrate 22 years of plundering the Annapolis Harbor with us this Wednesday on the 5:00 pm trip. All tickets are $22 in honor of our anniversary.

https://www.chesapeakepirates.com/anniversary-specials/

07/22/2024

$5 tickets left on the 2pm trip today. Come and get them!

07/22/2024

$5 TICKETS LEFT THIS AFTERNOON AT 2:00 pm, 3:30 pm and 5:00 pm. Come down and get them.
https://www.chesapeakepirates.com/pirate-adventures-5-day/

07/21/2024

$5 DAY INFORMATION FOR TOMORROW 7/22!
You cannot make a reservation for $5 Day, you must come purchase the tickets in person.
The line will form at our location: 311 Third St. Annapolis, MD 21403. There will be signage indicating where to form the line.
The door will open promptly at 8am
There are 45 tickets available on six sailing times at 9:30, 11:00, 12:30, 2:00, 3:30, and 5:00
A total of 270 tickets are available for the day
Every person, regardless of age, even an infant does need a ticket on the boat.
There is not a limit on the amount tickets one person can purchase. Early bird gets the treasure!
We will sell all the tickets on a sailing (9:30 first) before the next boat becomes available.
Once we have sold all 270 tickets for the six trips we will be sold out for the day. $5 tickets are only available on Monday, July 22nd, 2024.
Tickets are non-refundable unless Pirate Adventures makes the decision to cancel in the event of any steady rain, thunderstorms, or high winds. If we need to cancel the trip your tickets will be refunded when you arrive for your scheduled trip.
Tickets will be sold to standby passengers if you do not show for your trip or do not use all the tickets purchased.

07/13/2024

Some dads just go the extra mile 🏆

07/11/2024

Get the best deal on tickets when you celebrate our anniversary with us! Save $10 per ticket this Sunday.

Join us to celebrate our 22nd anniversary with $22 tickets once a week. A different sailing time each week will be posted by Sunday afternoons.

07/02/2024

Have you been to an Annapolis Blues game yet? We are little obsessed AND we have 25 tickets to give away to the LAST home game of the 2025 season. Comment on this post GO BLUES for a chance to score FREE tickets to the game on 7/6. ⚽️🦀💙💙

06/27/2024

Our own Captain Ruby is proud to be a founding board member of PlayAnnapolis, a nonprofit working to provide access to sports and recreation to ALL youth in the city of Annapolis. Listen to our story and consider purchasing tickets to our first fundraiser, a tailgate at the Annapolis Blues on 7/6. Find out more and PURCHASE TICKETS here: https://www.playannapolis.org/event-details/playannapolis-tailgate-fundraiser

Send a message to learn more

06/06/2024

Looking forward to the end of the school year? Summer is ALMOST HERE! We begin our daily sailing schedule MONDAY, 6/10. Grab $22 tickets next week in honor or our 22nd anniversary!

Join us to celebrate our 20th anniversary with $20 tickets once a week. A different sailing time each week will be posted on Sunday afternoons. 20th anniversary tickets can be purchased online.

06/01/2024

Happy pride month! Start things off with the parade 12 noon from city dock. ❤️🧡💛💚💙💜

05/31/2024

Gorgeous weekend on tap! Time to find the TREASURE! Make your reservation by calling (410) 263-0002.

05/23/2024

🍀 Lucky to be pirates. 🏴‍☠️ On the perfect day ☀️ in the best town ⚓️ x 2!!!! Thank you honorary pirates - crushed it!

04/19/2024

🌟🌟Pirate Season begins TOMORROW! Special events announced for the 2024 season including Princess Sails and the famous $5 Day. https://conta.cc/3JvDCKU

03/30/2024

Best summer job - apply now!

03/18/2024

What a weeked! Annapolis St. Patrick's Parade continues to knock it out of the park!

03/16/2024

PreSale tickets now on sale. To celebrate we'll be marching in the Annapolis St. Patrick's Parade tomorrow - see you there! 🍀 🎩 🌈

PreSale Tickets On Sale Now Spring Forward! Parade Sightings & Savings Spring is coming and we're dusting off the water cannons Come see us tomorrow at the Annapolis St. Patricks Day Parade! Pur

09/18/2023

happening here - how great was this September weekend?!? ☀️⛈🌈

09/04/2023

That’s a wrap on weekday trips - but still treasure to be found weekends in the fall! 🍂🍁🍃

09/03/2023

Well said 🦜💙

08/18/2023

That was a gorgeous day! 😎Summer is slipping away - come get your revenge on Pirate Pete while you can!

Address

311 3rd Street
Annapolis, MD
21403

Opening Hours

Monday	9am - 7pm
Tuesday	9am - 7pm
Wednesday	9am - 7pm
Thursday	9am - 7pm
Friday	8:30am - 7pm
Saturday	9am - 7pm
Sunday	9am - 7pm

Telephone

+14102630002

Website

https://www.chesapeakepirates.com/

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Still got it- #CaptCrabbyForever 🖤

$5 Dollar day coming your way MONDAY 7/22. Call for details (410) 263-0002.

$5 day coming up! Call (410) 263-0002 for full details!

Now sailing daily. Call for reservations (410) 263-0002!

Set course for an unforgettable birthday voyage where pirate dreams and mermaid wishes come true!

That’s a wrap on weekday trips - but still treasure to be found weekends in the fall! 🍂🍁🍃

4 tickets left on the 3:30!!! 1 ticket left on the 2:00 trip!!!

$5 Day is on MONDAY - bring us your $5 bills!!!!! https://www.chesapeakepirates.com/pirate-adventures-5-day/

PSA from Pirate Pete - Monday is $5 Day. https://www.chesapeakepirates.com/pirate-adventures-5-day/

$5 DAY MONDAY 7/17. If you know, you know. https://www.chesapeakepirates.com/pirate-adventures-5-day/

$5 Day is this coming Monday 7/17. NO RESERVATIONS - FIRST COME FIRST SERVED! Find out how $5 Day works. https://www.chesapeakepirates.com/pirate-adventures-5-day/