The Hip Hop R&B Yacht Party
The Hip Hop R&B Yacht Party is the best party on the water! Join us in Annapolis on Sunday, April 26, 2026. Party on the 95-foot Catherine Marie Yacht, dancing …
Spirits & Spirits
Don’t miss Spirits & Spirits! During this walking tour and cruise combination experience, you’ll brave the Historic District by foot, and hear spooky stories from your Ghost Guide. You’ll then …
Day on the Bay to St. Michaels
Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. Enjoy one complimentary non-alcoholic beverage on the way there! This quaint historic village offers fresh seafood, boutique shopping, …
Spa Creek Cruise
Step aboard our cozy launch, Miss Anne, for an intimate cruise up Spa Creek into the residential area of old Annapolis and Eastport. Cruise close to the homes and yachts …
Thomas Point Lighthouse Cruise
The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on our narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts; everyone …
Scenic Severn River Cruise
A spectacular, six-mile, narrated cruise from the Annapolis Harbor, past the U.S. Naval Academy seawall, and along the banks, wetlands, and waterfront homes of this protected river. Register here!
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. Register here!
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 …
Celebrate the Season in Annapolis with Watermark’s Holiday Experiences
There’s no place quite like Annapolis during the holiday season, when twinkling lights reflect off the water and history feels especially alive. This year, Watermark is offering a lineup of …
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 Academy. Hear the history of the Naval Academy, Annapolis’ …