Blue Angels flying over Baltimore

Special & Seasonal Cruises

Annapolis & Baltimore

Our special events are planned around the season, holidays, city celebrations, our area partnerships and just for fun!

Check this page often as we regularly add more Annapolis events (like music cruises!) and events in Baltimore. Our special cruises often coincide with Baltimore events and events in Annapolis like 4th of July Fireworks.

If something fun is happening on the water – or the sky – we’ll get you the best seat in town to enjoy it. Our Rock ‘N River cruises are a unique form of Annapolis entertainment and our Saturday night Annapolis Sunset Cruises with Live Music are one of the most fun things to do in Annapolis. Watermark has fun every day and these special cruises are all about fun.

Available Now

Rock the Harbor with Tranzfusion

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April 22, 2023

Tranzfusion is back by popular demand for a 2.5-hour live music cruise in Annapolis!

Book Now

Mother’s Day Cruise in Annapolis

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May 14, 2023

Treat the moms in your life to a lovely brunch cruise this Mother’s Day.

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Annapolis Sunset Cruise with Live Music

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May-September

This 90-minute cruise takes you out on the water to watch the sunset and enjoy live music.

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Full Moon Cruise

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June 3, 2023

Climb aboard to watch the sun set and the full moon rise over the water as you sip a cool cocktail and relax to live music.

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Father’s Day on the Bay to St. Michaels

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June 18, 2023

Enjoy Father’s Day with a cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore.

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Charm City Drag Cruise

-Baltimore-

June 23, 2023

June is Pride month, and Watermark is celebrating with a Charm City Drag Cruise! Join us for a raunchy, over-the-top drag show aboard our luxury yacht, Catherine Marie.

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Annapolis Fireworks Cruise on July 3rd

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July 3, 2023

Step aboard a Watermark boat for the annual Annapolis Fireworks Cruise on July 3rd.

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Annapolis Fireworks Cruise on July 4th

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July 4, 2023

Step aboard a Watermark boat for the annual Annapolis Fireworks Cruise on July 4th.

Book Now

Baltimore Fireworks Cruise on Annapolitan II

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July 4, 2023

Step aboard Annapolitan II to enjoy the Baltimore skyline and spectacular fireworks display.

Book Now

Baltimore Fireworks Cruise on Catherine Marie

-Baltimore-

July 4, 2023

Step aboard Catherine Marie to enjoy the Baltimore skyline and spectacular fireworks display.

Book Now

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise

-Annapolis-

Click “Book Now” for available dates.

Pass under the twin spans of the Bay Bridge and three Chesapeake lighthouses: Sandy Point Shoal, Baltimore Harbor, and Thomas Point on this award-winning 3- to 3½-hour cruise.

Book Now

Chesapeake Bay Trio

-Annapolis-

Click “Book Now” for available dates.

Join our live interpreter for an enjoyable 3-hour cruise from Annapolis’ historic harbor, up the scenic Severn River, then into the Chesapeake Bay, under the Bay Bridge, to Thomas Point Lighthouse.

Book Now

Coming Soon

Dog with sunglasses on a cruise

Dog Days of Summer Cruise

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Join us on Harbor Queen for a dog-friendly party on the water with our friends at the Anne Arundel County SPCA in support of their work.

Fall Foliage Bay Lighthouse Cruise

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This beautiful cruise includes three Chesapeake Bay lighthouses in addition to a spectacular view of the lovely fall foliage along the Annapolis waterfront.

Miss Anne decked out for the holidays

Jolly Express Cruise

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Annapolis’ favorite holiday activity makes its return for the 2023 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.

New Year’s Eve Cruises

-Annapolis & Baltimore-

Ring in the New Year on an exclusive and fun fireworks cruise aboard a luxury yacht with a DJ, dancing, desserts, and a complimentary glass of champagne.

Rock the Harbor with Tranzfusion!
Tickets for Saturday, April 22nd now available
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