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FEATURED EVENTS
Day on the Bay in St. Michaels
Journey to St. Michaels, Maryland
Spend a Day on the Bay

Cruise across the Bay to spend over three hours at this quaint, historic village, enjoying fresh seafood, boutique shopping and historic sites, all within walking distance. Cash beverage and snack service onboard. Ticket includes complimentary admission to the Chesapeake Bay Maritime Museum and non-alcoholic beverage and doughnut on the morning cruise to St. Michaels.

Itinerary (approximate):
  • 9:30 am: Check-in at Annapolis City Dock.
  • 10 am - 12:00 pm: Cruise to St. Michaels. Complimentary coffee and doughnuts.
  • 12:00 pm - 3:30 pm: Free time in St. Michaels. Museum admission included.
  • 3:30 - 5:30 pm: Cruise back to Annapolis.


  • Reservations are strongly recommended for all "Day on the Bay Cruises". Vessels cruise rain or shine. Tickets are non-refundable. Online sales available until 6:00am day of the cruise. Walkups Welcome

    Blue Angels Demonstration Cruises in Baltimore
    Practice Day and Demonstration Day cruises to experience this elite team of Navy pilots as they streak across the Baltimore sky. Part of the Star Spangled 200 celebration. Time adjustment might be necessary due to the time of the Blue Angels performance.

    Star-Spangled 200 Sailabration 90 Min Cruise
    An international parade of tall ships and naval vessels sails into Baltimore June 13-19 for the Star-Spangled Sailabration, the bicentennial celebration of "The Star-Spangled Banner" and the War of 1812. The unique and one time weeklong event features more than two dozen ships flanking Baltimore's Inner Harbor and special air and water displays. Watermark's 90 minute Sailabration Cruise features an interpreter providing live narration of the harbor, the vessels in for the event and an overview of the 1812 history about the Baltimore Harbor.

    National Anthem Tour by Sea - 60 Min.
    View the Baltimore Harbor aboard a Watermark Yacht while enjoying our "1812 Harbor Cruise". Accompanied by lively narration describing areas around the harbor, you can see the Baltimore harbor of today while hearing about the lives of people during the War of 1812. These 60 minute cruises depart from the Light Street Piers in climate- controlled vessels with top deck open views of the harbor.

    African-American Heritage Tour
    In Partnership with the Kunta Kinte-Alex Haley Foundation

    Trace the rich and authentic journey of African Americans in Annapolis and explore their contributions both nationally and internationally. Key historical sites include the Kunta Kinte-Alex Haley Memorial and the Thurgood Marshall Memorial. Any event may be canceled due to severe weather, lack of participation or mechanical breakdown. - no refunds

    Baltimore Inner Harbor Cruise
    Step aboard Annapolitan II for a 45-minute cruise introducing Baltimore and the renaissance of the Inner Harbor. See Federal Hill, the city skyline, Fells Point, the USS Constellation and catch a glimpse of Ft. McHenry. Join us today. Check in time is 15 minutes prior to your cruise. Welcome aboard!

    Any event may be canceled due to severe weather, lack of participation or mechanical breakdown.

    Bay Lighthouses Cruise
    Lighthouses Cruise: Explore the Treasures of the Chesapeake Bay

    Thomas Point Lighthouse, Sandy Shoal Lighthouse and Baltimore Shoal Lighthouse

    Join Watermark for our award winning "Bay Lighthouses Cruise." During this 2 1/2 hour cruise you will pass under the twin spans of the Bay Bridges and pass by Sandy Point Shoal, Baltimore Harbor, and Thomas Point lighthouses.

    Any event may be canceled due to severe weather, lack of participation or mechanical breakdown.



    City Lights Cruise
    The City Lights Cruise is an evening cruise around the Inner Harbor. Step aboard the Annapolitan II for a twilight cruise to see the lights of the buildings reflecting off of the water and the iconic Domino Sugar sign lit up.

    Check in time is 15 minutes prior to your cruise.

    Civil War in Annapolis Tour
    The Civil War and mid 1800s period is explored through local historic sties and people from that time. Uncover many of the fascinating stories and events that unfolded in Annapolis, the role the city played during the war and about how city residents were impacted during this dramatic time in America.



    Colonial Stroll
    Stroll with a Colonial-Commissioning Week Special!
    Tour the heart of Annapolis as our colonial-attired guides lead the way. Tour includes exteriors of the Maryland State House and famous historic mansions.

    *Building interiors when available.


    Fireworks July 3rd Cruise Annapolis
    Enjoy the test seat in town for a local neighborhood Fireworks display on July 3rd. Snacks included, cash bar.

    NO REFUNDS.

    Fireworks July 4th Cruise Annapolis
    Enjoy the best seat in town for the spectacular Maryland Fourth of July fireworks show. Snacks included. DJ entertainment. Cash bar.

    No Refunds

    Fireworks July 4th Cruise Baltimore
    Enjoy the best seat in town for the spectacular Baltimore fireworks aboard a Watermark yacht. The cruise includes snacks and cash bar. DJ entertainment.

    NO REFUNDS

    Four Centuries Walking Tour
    Our colonial-attired tour guides will bring history to life in this 2 1/4 hour walking tour. Stroll through historic Annapolis, explore the interior of the Maryland State House, and be inspired by the sights and sounds of the U.S. Naval Academy, home to over 4,000 midshipmen. Building interiors when available.

    All guests 16 years of age and older must have a photo ID.



    Historic Ghost Walk
    As the sun sets and darkness wraps the streets of historic, and some say, haunted Annapolis, a knowledgeable guide will lead you on a journey sharing tales by candlelight of the spirits who dwell in the town's 18th century buildings and linger in the mist. This is a 1 1/2 hour Annapolis ghost tour.

    Please click here to book our Special Ghost Tour (available in October).




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