Bay Weekly Calendar

Recurring

Sunset Cruise

Annapolis City Dock Dock Street, Annapolis, MD

Join our crew for an extraordinary sunset on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda).

$60

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

Sunset Cruise

Annapolis City Dock Dock Street, Annapolis, MD

Join our crew for an extraordinary sunset on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda).

$50

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

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

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

Queens on Queen

Annapolis City Dock Dock Street, Annapolis, MD

June is Pride month, and Watermark is celebrating with queens on the Queen! Join us for a raunchy, over-the-top drag queen show. These fabulous queens will entertain you with comedic and musical acts throughout the 2.5-hour cruise. You're in store for an evening full of hilarious skits, side-splitting performances and whatever other absolute ridiculousness these […]

$49.00

Queens on Queen

Annapolis City Dock Dock Street, Annapolis, MD

June is Pride month, and Watermark is celebrating with queens on the Queen! Join us for a raunchy, over-the-top drag queen show. These fabulous queens will entertain you with comedic and musical acts throughout the 2.5-hour cruise. You're in store for an evening full of hilarious skits, side-splitting performances and whatever other absolute ridiculousness these […]

$49.00

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

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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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