FEATURED

LOL Annapolis welcomes you to the greatest comedy in central Maryland! The Comedy Zones joins us to welcome nationaly touring comedians as they stop in to visit Annapolis Maryland. Get your tickets online and join us to Laugh Out Loud Annapolis!

LEARN MORE

Two Days of Pirate Adventure with pirate Encampments, Live Mermaids, Magic, Music, and Mayhem!

LEARN MORE
Upcoming Events
June 2023
Fri, June 23
LOL ANNAPOLIS

  • Kevin Lee

  • with Irwin Loring

Doors: 7pm // Show: 7:30pm
$22.50 to $30
Crowne Plaza Hotel
Buy Tickets
More Info
July 2023
Thu, July 20
Pirate Island Events

Reggae Bay Day

Doors: 6pm // Show: 6pm
$45
Watermark Journey’s Harbor Queen
Buy Tickets
More Info
April 2024
Sat, Apr 27

Pirate’s Parlay of the Chesapeake 2024

Doors: 12pm // Show: 12pm
$1 to $90
Anne Arundel County Fairgrounds
Buy Tickets
More Info
Sat, Apr 27

Postponed-Pirate’s Parlay of the Chesapeake

Doors: 12pm // Show: 12pm
Anne Arundel County Fairgrounds
Not Available Online
More Info

SIGN UP

Join our email list!

Just Announced
sat, Apr 27

Pirate’s Parlay of the Chesapeake 2024

Anne Arundel County Fairgrounds
Tickets
thu, July 20
Pirate Island Events

Reggae Bay Day

Watermark Journey’s Harbor Queen
Tickets
sat, Apr 27

Postponed-Pirate’s Parlay of the Chesapeake

Anne Arundel County Fairgrounds
Unavailable
fri, June 23
LOL ANNAPOLIS

  • Kevin Lee

  • with Irwin Loring
Crowne Plaza Hotel
Tickets

SPONSORS

If you are interested in sponsoring or volunteering a Pirate Island Event, please contact Darrin at [email protected]