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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 Wednesday Night Races Cruises 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

Miss Anne decked out for the holidays

Jolly Express Cruise


Select dates December 2021

Hop aboard Miss Anne, all decked out for the holidays. Enjoy hot cocoa, holiday music, and good cheer on Captain Santa’s “sleigh ride.”

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New Year’s Eve Fireworks Annapolis Cruise


December 31st, 2021

Make your New Year’s Eve memorable with this exclusive and fun fireworks cruise aboard a luxury yacht. Desserts, dancing, music, and more!

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Lights Parade Package


December 11th, 2021

Dine at the Severn Inn and enjoy a spectacular dessert cruise aboard our luxury yacht, Catherine Marie, to watch the 2021 Eastport Yacht Club Lights Parade.


Music Cruise Baltimore

Live Music Cruises

-Annapolis & Baltimore-

May-October 2021

Click below to learn more about our upcoming live music cruises in Annapolis and Baltimore. Featuring local bands, a full bar, and spectacular views, these cruises really rock the boat!

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Coming Soon

Key Bridge Cruise


Enjoy a 90-minute cruise to and from the Key Bridge featuring narration of the Baltimore Harbor’s rich history.

Harbor Queen top deck shot

Schooner Races


A great opportunity to get out on the water to see the start of the Great Chesapeake Bay Schooner Race.  About 30 historic  & modern schooners race to Portsmouth, Va. in this annual competition.

Chesapeake Bay Heritage Cruise

Chesapeake Bay Heritage


Enjoy beautiful shoreline scenery as our Maryland Certified Chesapeake Bay Storyteller connects you to the treasure that is the Bay.

City lights

Light City Cruises


View the festival lights from the water. This special themed cruise features music, light-up beverages, and spectacular views of Baltimore’s skyline.

Dog with sunglasses on a cruise

Dog Days of Summer


An annual cruise to benefit the Anne Arundel County SPCA.  Bring your favorite four-legged friend, leashed please, and have them bob for hot-dogs on the top deck.

Watermark Cruise Boat

Watermens Festival


Cruise to the annual Watermen’s Festival in St. Michaels on Maryland’s Eastern Shore.  The festival celebrates watermen and their heritage.  Fun for the entire family.

Chesapeake Bay Maritime Museum boats docked

OysterFest Cruise


Cruise to the St. Michaels OysterFest at the Chesapeake Bay Maritime Museum.  OysterFest features live music, cooking demonstrations, children activities and more.

Cruise to the WineFest


Travel across the Bay to the St. Michaels Wine Festival.  Enjoy wine tasting venues throughout the town.  This cruise will sell out.

Fleet Week & Airshow


A signature Watermark event! There’s no better way to experience the U.S. Navy Blue Angels than from on a yacht as they buzz overhead.

Raven sunset in Baltimore

New Year’s Eve


Make your New Year’s Eve memorable with this special celebration on the water.  Ring in the New Year on an exclusive and fun fireworks cruise aboard a luxury yacht.  Desserts, dancing, music, and more!

Dublin 5 Band



It’s our annual halfway to St. Patrick’s Day cruise.  Dublin5, a local high energy Irish-rock band is an Annapolis favorite.

Fireworks over Baltimore Inner Harbor

July 4th Fireworks

-Annapolis & Baltimore-

Step aboard a Watermark yacht for the annual Annapolis and Baltimore fireworks cruises. Enjoy the spectacular demonstrations over the water.

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise


See Thomas Pt Shoal, Sandy Pt Shoal, and Baltimore Harbor Lighthouses on Watermark’s award winning cruise. Our historically-attired lighthouse keeper provides live interpretation for a thoroughly enjoyable cruise.

Cruising the harbor on the Raven

July 4th DJ & BBQ


Cruise on Raven, our 99′ luxury yacht during Baltimore’s fireworks spectacular.  Enjoy BBQ, music from a local DJ, and an Open Bar!  This is how you celebrate independence day.

Thomas Pt Lighthouse and Watermark Flag

Chesapeake Bay Trio


Join our live interpreter for a 3 hour cruise of Annapolis’s historic harbor.  Enjoy local tales of the sea and cruise under the famous Chesapeake Bay Bridge.

Fall Foliage on Cabaret 2

Fall Foliage Cruise


October 2022

This cruise includes three Chesapeake Bay Lighthouses and gives guests the spectacular view of the lovely fall foliage along the waterfront. A local favorite.

New Year’s Eve Charm City Cruise


December 2022

Ring in the New Year on an exclusive and fun cruise aboard a luxury yacht with dancing, desserts, and a live DJ.