Annapolis is a beautiful historic seaport that’s great to explore by water!
Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an Unforgettable Journey. 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.
Come on down and find us at Annapolis City Dock, 1 Dock Street and look for the Red umbrella!
Annapolis by Land & Sea
Family Field Trip
A family field trip for students and parents missing traditional field trips this year. Enjoy a Colonial Stroll through Historic Annapolis and an Annapolis Harbor & USNA Cruise.
Mother’s Day Cruise in Annapolis
Treat the moms in your life to a lovely cruise this Mother’s Day. Our 95-foot luxury yacht, Catherine Marie, will take you out on the water for a leisurely 90-minute cruise. There will be live music, charcuterie boxes, and a signature drink, The Momosa.
Annapolis Harbor & USNA
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’ role as a historic seaport, the region’s waterways, and catch a glimpse of the Bay Bridge.
Spa Creek Cruise
Step aboard our cozy launch for an intimate cruise up Spa Creek into the residential area of Old Annapolis, Eastport, and the banks of the U.S. Naval Academy.
Day on the Bay to St. Michaels
Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. Enjoy fresh seafood, boutique shopping, and historic sites all within walking distance.
Annapolis Sunset Cruise
Enjoy music playing, the sun setting, and a cool beverage from our River Run Bar as you relax on this hour long cruise through the Annapolis Harbor.
Blue Angels Practice Day Cruise
Watermark is offering this 2-hour cruise aboard our boats to view the Blue Angels practice day demonstration on May 25th. Experience this elite team of Navy pilots as they streak across the Annapolis sky to celebrate Naval Academy graduates. Watch this impressive air show from the best seat in town, a Watermark yacht!
Blue Angels 3-Hour Cruise
Watermark is offering this 3-hour cruise aboard our boats to view the Blue Angels demonstration on May 26th. Experience this elite team of Navy pilots as they streak across the Annapolis sky to celebrate Naval Academy graduates. Watch this impressive air show from the best seat in town, a Watermark yacht!
Annapolis Sunset Cruise with Live Music
This 90-minute Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Enjoy live music from your favorite local Maryland musicians and beautiful scenery as you relax with a cool drink.
Scenic Severn River Cruise
A spectacular 6-mile cruise on the beautiful Scenic Severn River and historic Annapolis Harbor; includes the banks of the United States Naval Academy
Chesapeake Bay Bridges
Cruise through Annapolis’ historic harbor, by the United States Naval Academy, and under the twin spans of the famous Chesapeake Bay Bridge.
Thomas Point Lighthouse
View this National historic landmark as you cruise the Chesapeake Bay on a narrated cruise. Not just for lighthouse enthusiast; everyone loves it!
Water Taxi Service
Hop on a taxi to visit your favorite restaurant or to get downtown from Eastport. Taxi’s operate in the Annapolis Harbor, including Spa Creek and Back Creek
Special or Seasonal Cruises
From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonal cruises throughout the year. Click below to learn more.
From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonl cruises throughout the year. Click below to learn more.