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!
Hop aboard Miss Anne, all decked out for the holidays. Enjoy hot cocoa, holiday music, and good cheer. Bring your own blankets and enjoy Captain Santa’s “sleigh ride.”
Colonial Stroll & Cruise – Holiday Style
Traditions of the holiday season will be highlighted along with our classic Colonial tales as you stroll the quaint streets of the Historic District. Your guide will deliver you to enjoy a cruise aboard the festively decorated “Miss Anne”.
Captain Santa’s Cruise
Bring the family on this water ride where cheery holiday music will be playing. Captain Santa will hand out candy canes to all.
Spirits & Spirits
You’ll be led through haunted waterways by boat and brave the Historic District by foot while your guide entertains you with nautical myths, pirate tales, and ghost stories.
Annapolis Harbor & USNA
Step aboard to experience a narrated cruise of historic Annapolis and the banks of the U.S. Naval Academy. An Annapolis tradition and fun for the whole family.
Spa Creek Tour
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.
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.
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!
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.