Bay Weekly Calendar

Bay Lighthouses Cruise

Annapolis City Dock Dock Street, Annapolis, MD

See Thomas Pt Shoal, Sandy Pt Shoal and Baltimore Harbor Lighthouses on Watermark’s award winning Bay Lighthouses Cruise. Join us for 3 to 3.5 hours exploring these treasures of the Chesapeake Bay. Our historically attired lighthouse keeper provides live interpretation for a thoroughly enjoyable cruise. Feel free to bring your lunch (food only). We have […]

$11 – $49

Recurring

Jolly Express Cruise

Annapolis City Dock, Slip 2 1 Dock Street, Annapolis, MD, MD

Hop aboard Miss Anne, all decked out for the Holidays and for a Spa Creek "sleigh ride" on the Jolly Express. Miss Anne will be adorned with reindeer spirit for an intimate cruise including hot cocoa, holiday music, and good cheer. Bring your own blankets and enjoy the cruise with "Captain Santa" at the helm.

$13.00 – $23.00

Mother’s Day Cruise in Annapolis

Annapolis City Dock Dock Street, Annapolis, MD

Treat the moms in your life to a lovely cruise this Mother’s Day. Our 95-foot luxury yacht, Catherine Marie, will take you out on the water for a leisurely 90-minute cruise. There will be live music, charcuterie boxes by Vintage Views Bar, and a signature drink, The Momosa. To create a safe, socially distanced experience […]

Table pricing

Caribbean Vibes on the Chesapeake Cruise

Annapolis City Dock Dock Street, Annapolis, MD

Enjoy a leisurely 3-hour sunset cruise on the Chesapeake to the tune of live music from steel drum band, Caribbean Vibes. Beverages and snacks will be available for purchase from our full bar.

$49.00

Summer Music Cruise

Baltimore Finger Piers 555 Light St, Baltimore

Enjoy a fun, 3-hour, live music cruise hosted in partnership with Pirate Island Events. On August 19th in Annapolis, the Chris Sacks Band will play its mixture of red-blooded American music and the blue seawaters of the Caribbean. On September 15th in Baltimore, the Caribbean Vibe Steel Drum Band will play its "music from the […]

$49.00

Harbor Queen Halloween with Honest Lee Soul

Annapolis City Dock Dock Street, Annapolis, MD

Climb aboard Harbor Queen to celebrate Halloween. Honest Lee Soul will be back by popular demand for an incredible live music performance. Add spirit to your night with our specialty cocktail at a special price: the Poison Apple ($7/cocktail). This event is 21 and over only. Costumes encouraged! This is a Halloween event you won't […]

$53.00

Mother’s Day Cruise in Annapolis

Annapolis City Dock Dock Street, Annapolis, MD

Treat the moms in your life to a lovely brunch cruise this Mother's Day. Our 95-foot luxury yacht, Catherine Marie, will take you out on the water for a leisurely 2-hour cruise with live music by Guava Jelly. Included in the ticket is a buffet omelette station by The Original Omelette Man and one complimentary […]

$45 – $90

Harbor Queen Hoedown

Annapolis City Dock Dock Street, Annapolis, MD

Yee-haw! Join us for a Harbor Queen Hoedown featuring the Summer Knights Band. Kick off summer with your best pair of boots and cowboy hat, and dance the night away.

$45.00

Annapolis Fireworks Cruise on July 4th

Annapolis City Dock Dock Street, Annapolis, MD

Step aboard a Watermark boat for the annual Annapolis Fireworks Cruise. On July 4th, enjoy the City of Annapolis' spectacular Fourth of July fireworks from the best seat in town as you cruise the historic harbor. A selection of delicious complimentary desserts will be available. Alcoholic and non-alcoholic beverages will be available for purchase from […]

$75.00

Day on the Bay to St. Michaels

Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. This quaint historic village offers fresh seafood, boutique shopping, and historic sites all within walking distance during your approximately 3 hours ashore, followed by the return cruise to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included.

Recurring

Jolly Express Cruise

Annapolis City Dock Dock Street, Annapolis, MD

Jolly Express Cruise Ho, Ho, Ho, and a Bottle of Rum! Well, maybe not the rum, but Santa returns to the shores of Annapolis with his Jolly Express Cruise! Grab the kids and family and start a new holiday tradition! Miss Anne will be adorned with festive reindeer spirit and a jolly red nose for […]

$25

New Year’s Eve Annapolis Fireworks Cruise

Annapolis City Dock Dock Street, Annapolis, MD

Make your New Year's Eve memorable with a special celebration on the water. In Annapolis, step aboard a Watermark’s flagship yacht, Catherine Marie, for a New Year’s Eve Annapolis Fireworks Cruise. Enjoy dancing, desserts, a DJ, a complimentary glass of bubbly, and fireworks. This event is 21 and over.

$97.00

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