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Group Cruises

Planning a trip to Annapolis or Baltimore for your family, social, military, reunion, or church group?

Watermark has the perfect cruise for your event.

Group pricing starts at 20 guests.

Cruise these Historic Seaport cities and beyond while taking in unbelievable views and the sights, history and sounds of these two picturesque Inner Harbors.

Our boats have a full bar service with light snacks available for purchase and restrooms on board.  Most of our vessels are handicapped accessible and climate controlled.

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Download our 2022 Group Experiences Profile Sheet here.

Group posing in front of yacht

Harbor Queen
Annapolis Harbor and U.S. Naval Academy Cruise

40min cruise – Annapolis

You and your group can step aboard Harbor Queen for a 40-minute narrated cruise of the historic Annapolis Harbor and the banks of the U.S Naval Academy. This is a great introduction to Annapolis for first time guests.

Lady Sarah and Cab
Scenic Cruises

90min Cruise – Annapolis

Select one of our scenic 90 minute cruises:

Scenic Severn River Cruise – A spectacular 6-mile cruise on the beautiful Severn River.

Chesapeake Bay Bridges Cruise – Marvel at the engineering feat as you cruise under the twin spans of the Bay Bridges

Thomas Point Lighthouse Cruise – Cruise the Chesapeake Bay to view this National Historic Landmark.

Captain on the ship
Chesapeake Bay Trio: River. Lighthouses. Bridge

3 Hour Cruise – Annapolis

A live interpreter shares your connection with the waters of Annapolis, the crown jewel of the Bay, through rich and diverse legends and lore. Hear tales of smuggling, rum running, and piracy and the legend of Chessie, the Chesapeake Bay Sea Monster. Also included will be a short history of Kent Island including information on its original North American inhabitants.

Bay Lighthouses Cruise

3 Hour Cruise – Annapolis – A Four Rivers Heritage Award Winner

Pass under the twin spans of the Bay Bridges and by Sandy Point Shoal, Baltimore Harbor, and Thomas Point Lighthouses. Cruise offers a live narration by our turn of the century lighthouse keeper.

Cruise to St. Michael's
Day on the Bay to St. Michaels

7.5 Hour Cruise – Annapolis

Enjoy a “Day on the Bay” cruising from Annapolis to historic St. Michael’s, Maryland with 3 hours of free time to explore specialty shopping, gourmet dining or touring the Chesapeake Bay Maritime Museum. Price includes admission to the museum along with complimentary non-alcoholic beverage and doughnuts on the morning cruise.  Roundtrip 10:00 AM–5:30 PM

In Baltimore Harbor

Legends and Sights of Baltimore

2.5 Hour Cruise – Baltimore

Baltimore history and Baltimore charm! Hear tales of the harbor and port from aboard Raven, the newest yacht in Watermark’s fleet. A live interpreter will share stories about the founding of Fell’s Point and the “red light district,” Edgar Allen Poe’s presence in Baltimore, the development of the Clippers and Francis Scott Key. Sights include the National Aquarium, The Domino Sugar Factory, Fort McHenry and the Key Bridge.


National Anthem Tour

National Anthem Tour by Sea

60min Cruise – Baltimore

1812 Narrated cruise: Step aboard a vessel that will transport you to a time when Baltimore residents defended their homes, businesses, and land. This is a narrated 1812 Baltimore Harbor Cruise. Cruise by the spot where Francis Scott Key watched the “bombs bursting in air” and wrote our National Anthem while aboard a British Ship


Baltimore Harbor Cruise

Baltimore Harbor Cruise

45min Cruise – Baltimore

You and your group can step aboard Annapolitan II for a 45-minute narrated cruise of Baltimore’s Inner Harbor and nearby landmarks. This cruise is a wonderful introduction to Baltimore for first time guests.



Reserve your cruise today. Call us at 410-268-7601 x 200


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Full Moon Cruise
Live music by Chris Sacks Band!
Saturday, June 3rd
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