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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 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

Full Moon Cruise

-Annapolis-

August 12th, 2022

Climb aboard to watch the sun set and the full moon rise over the water. Sip a cool cocktail and relax to live music by Stephen Henson.

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Cruise to the Watermen’s Festival

-Annapolis to St. Michaels-

August 14th, 2022

Cruise roundtrip to the Annual Watermen’s Appreciation Day in St. Michaels on Maryland’s Eastern Shore. The festival celebrates Chesapeake watermen and their heritage.

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Dog with sunglasses on a cruise

Dog Days of Summer Cruise

-Annapolis-

August 17th, 2022

Bring your pup on board, and join us for a dog-friendly party on the water with our friends at the Anne Arundel County SPCA in support of their work.

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Music Cruise Baltimore

Live Music Cruises

-Annapolis & Baltimore-

May-October 2022

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!

Learn More

Baltimore Sunset Cruise with Live Music

-Baltimore-

September 3rd, 2022

This 90-minute Baltimore Sunset Cruise aboard a Watermark yacht takes you out on the water to watch the sunset to the tune of live music.

Book Now

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise

-Annapolis-

Select dates April-October

See Thomas Point Shoal, Sandy Point Shoal, and Baltimore Harbor lighthouses on Watermark’s award-winning 3 to 3.5-hour Bay Lighthouses Cruise.

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Baltimore Fireworks Cruise on Annapolitan II

-Baltimore-

September 10th, 2022

Step aboard Annapolitan II to enjoy the Baltimore skyline and spectacular Fleet Week fireworks display from the best seat in town as you cruise the Inner Harbor.

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Songwriters on the Severn

-Annapolis-

September 17th, 2022

Celebrate the Annapolis Songwriters Festival with a 90-minute live music cruise on the Severn River, featuring members of The Loving Mary Band including Marti Frederiksen, Rebecca Lynn Howard, Elisha Hoffman, and Kylie Sackley.

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Rock the Harbor with Tranzfusion

-Annapolis-

September 30th, 2022

Tranzfusion is back by popular demand for a live music cruise in Annapolis! Tranzfusion, a classic rock band from Salisbury, Maryland, will rock the Harbor on Harbor Queen on this 2.5-hour cruise.

Book Now

Fall Foliage Bay Lighthouse Cruise

-Annapolis-

October 2022

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

Book Now

Coming Soon

Dublin 5 Band

Dublin5

-Annapolis-

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

Harbor Queen top deck shot

Schooner Races

-Annapolis-

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

-Annapolis-

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

-Baltimore-

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

Chesapeake Bay Maritime Museum boats docked

OysterFest Cruise

-Annapolis-

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

-Annapolis-

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

-Baltimore-

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.

Thomas Pt Lighthouse and Watermark Flag

Chesapeake Bay Trio

-Annapolis-

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.

Miss Anne decked out for the holidays

Jolly Express Cruise

-Annapolis-

Select dates December 2022

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

Lights Parade Holiday Package

-Annapolis-

December 2022

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

New Year’s Eve Fireworks Annapolis Cruise

-Annapolis-

December 31st, 2022

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

New Year’s Eve Charm City Cruise

-Baltimore-

December 31, 2022

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

4th of July Fireworks Cruises

-Annapolis & Baltimore-

July 3rd & 4th, 2023

Step aboard a Watermark boat for the annual fireworks cruise to enjoy the fireworks displays from the best seat in town.

Check out our special event cruises!
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