• Jolly Express Cruise

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Don't miss the Jolly Express Cruise! Annapolis’ favorite holiday activity makes its return for the 2025 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute “sleigh ride” including hot cocoa, holiday music, and good cheer. Captain Santa or Mrs. Claus will be at the helm during this festive evening cruise …

    $15 – $28
  • New Year’s Eve Annapolis Yacht Party

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Make your New Year’s Eve memorable with this special family-friendly celebration on the water in Annapolis. Cruise aboard a Watermark yacht and dance to DJ Lampdawg’s tunes. Enjoy a complimentary glass of bubbly for the adults and a cup of cocoa for the kids, and a front-row seat of Annapolis’ fireworks display. Celebrate the end …

    $59 – $109
  • Annapolis Harbor & USNA Cruise

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Step aboard the classic Harbor Queen for a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval Academy. Hear the history of the Naval Academy, Annapolis’ role as a historic seaport, the region’s waterways, and catch a glimpse of the Chesapeake Bay Bridge. This cruise is an Annapolis tradition and fun …

    $10 – $25
  • Annapolis Sunset Cruise

    Annapolis Sunset Cruise

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Our Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Enjoy a fun music playlist and beautiful scenery as you relax with a cool drink. Beverages and snacks are available for purchase from our full bar. Get your tickets here!

    $18 – $35
  • Thomas Point Lighthouse Cruise

    Thomas Point Lighthouse Cruise

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on our narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts; everyone loves it! Get your tickets here!

    $18 – $35
  • Chesapeake Bay Bridge Cruise

    Chesapeake Bay Bridge Cruise

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Cruise under the twin spans of the Bay Bridge, one of the longest over-water structures in the world, while enjoying sights of the Chesapeake Bay. Register here!

    $18 – $35