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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

Bay Lighthouse

Bay Lighthouse Cruise

-Annapolis-

Multiple Dates

See Thomas Pt Shoal and Baltimore Harbor Lighthouse on our Bay Lighthouses Cruise.  Our historically attired lighthouse keeper provides live interpretation.

Book Now

Thomas Pt Lighthouse and Watermark Flag

Chesapeake Bay Trio

-Annapolis-

Multiple Dates

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.

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Fall Foliage on Cabaret 2

Fall Foliage Cruise

-Annapolis-

Multiple Dates

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

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Watermark Cruise Boat

Watermens Festival

-Annapolis-

Cancelled

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.

Book Now

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.

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Cruise to the WineFest

-Annapolis-

October 3rd & 4th, 2020

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

Book Now

Coming Soon

July 3rd Fireworks

-Annapolis-

Cancelled

Cruise the scenic Severn River to a local community’s spectacular fireworks demonstration aboard the Harbor Queen, the best place to watch the fireworks.

July 4th Fireworks

-Annapolis-

Cancelled

Step aboard a Watermark yacht for the annual Annapolis Fireworks Cruise.   Enjoy the spectacular demonstration brought to you by the city of Annapolis.

Fireworks over Baltimore Inner Harbor

July 4th Fireworks

-Baltimore-

Cancelled

Step aboard a Watermark yacht for the annual Baltimore Fireworks Cruise.   Enjoy the spectacular demonstration brought to you by the city of Baltimore.

Cruising the harbor on the Raven

July 4th DJ & BBQ

Cancelled

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.

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.  This cruise sells out so reserve your tickets now.

Fleet Week & Airshow

-Baltimore-

A signature Watermark event!  2020 features the U.S. Navy Blue Angels and there no better way to experience them from on a yacht as they buzz overhead.

National Anthem Tour

National Anthem

-Baltimore-

The National Anthem Tour by Sea is a narrated cruise in Baltimore celebrating the heroic role of Baltimore and her residents during the War of 1812.

Dog with sunglasses on a cruise

Dog Days of Summer

-Annapolis-

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.

Jolly Express

Jolly Express

-Annapolis-

Hop aboard Miss Anne, all decked out for the holidays.  Enjoy hot cocoa, holiday music, and good cheer.  Cuddle up under the blankets as Captain Santa takes you on a “sleigh ride.”

Catherine Marie by the USNA

Parade of Lights

-Annapolis-

Dine at the waterfront Severn Inn, then enjoy a spectacular Dessert Cruise on the luxurious Catherine Marie to watch the Annual Eastport Yacht Club Lights Parade.

Catherine Marie sunset

New Year’s Eve

-Annapolis-

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!

Raven sunset in Baltimore

New Year’s Eve

-Baltimore-

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!

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-

October 31st, 2020

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

Music Cruise Baltimore

Live Music Cruises

-Annapolis & Baltimore-

Click below to learn more about our upcoming music cruises in Annapolis & Baltimore.  Featuring local bands, these cruises really rock the boat!

Learn More