Jolly Express Cruise
Join in on the Jolly Express Cruise! Annapolis’ favorite holiday activity makes its return for the 2024 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate …
Annapolis Harbor & USNA Cruise
Join Watermark for the Annapolis Harbor & USNA Cruise! Step aboard the classic Harbor Queen for a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval …
Cruise to OysterFest
Cruise round-trip from Annapolis to the St. Michaels OysterFest at the Chesapeake Bay Maritime Museum on Maryland’s Eastern Shore. OysterFest celebrates the Chesapeake’s favorite bivalve and features live music, retriever …
Sunset Cruise on the Chesapeake
Don’t miss the Sunset Cruise on the Chesapeake! Join our crew for a two-hour extraordinary cruise enjoying the golden hour on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned …
National Anthem Tour by Sea
Observe the Baltimore Harbor while enjoying a lively narration with the National Anthem Tour! You will be transported to a time when Baltimore residents defended their homes, businesses, and land …
Schooner Race Watch
Don’t miss the Annual Great Chesapeake Bay Schooner Race Watch aboard the 74-foot, Schooner Woodwind II! Join in the excitement and watch the start of the 130-mile race from Annapolis …
Scenic Severn River Cruise
Don’t miss the Scenic Severn River Cruise! It’s a spectacular six-mile narrated cruise on the beautiful scenic Severn River. View the historic Annapolis Harbor including the banks of the U.S. …
Chesapeake Bay Bridge Cruise
Cruise under the twin spans of the Bay Bridge, one of the longest over-water structures in the world, while enjoying sights of the Chesapeake Bay with Watermark’s Chesapeake Bay Bridge …
Songwriters on the Severn
Don’t miss Songwriters on the Severn! Celebrate the Annapolis Songwriters Festival with a three hour live music cruise on the Severn River. Featuring performances by July Moon, The Heels, and …
Annapolis Sunset Cruise
Our Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Enjoy a fun music playlist and beautiful scenery …