Cruises on the Bay

Cruises on the Bay

Cruises on the Bay℠ by Watermark® offers fun Annapolis cruises and Baltimore cruises that vary in duration, narration style – both recorded and live – and locales explored. Friendly Captain and crew will host you on an unforgettable journey. Come venture around the local Maryland waterways aboard the Chesapeake Bay's largest private fleet. Experience the scenic beauty and the unique treasures that can only be found in America's largest estuary. Choose from a variety of sightseeing cruises offered daily throughout the boating season. Whether you are looking for things to do in Baltimore, family activities, things to do in Annapolis, or a nice outing with a loved one, Watermark cruises has the perfect cruise for you!

Cruising the Chesapeake is easy with Watermark. Take a Chesapeake Bay day cruise on a Day on the Bay to St. Michaels Cruise…the cruise that started it all over 40 years ago! With two home ports – Annapolis and Baltimore – there are plenty of opportunities to get on the water. Take a Chesapeake Bay cruise around the Bay’s lighthouses, an Annapolis cruise learning about this historical city and its rich maritime culture, or a Baltimore cruise for a beautiful view of the city from the water.

Highlights of Cruises on the Bay by Watermark:

  • Cruises are pet-friendly as long as dogs are friendly and leashed. Dogs cruise free!
  • Restrooms on board for all Baltimore cruises and all Annapolis cruises except for Spa Creek tours on the cozy Miss Anne.
  • Air conditioned vessels in Baltimore. In Annapolis, most longer cruises are on vessels with air conditioning. Bonus: on hot days, it’s always cooler on the water!
  • Full bars on board most vessels. Cozy up to the River Run Bar for a mixed drink, beer, wine, soda or water. Harbor Queen and Annapolitan II serve up fresh popcorn every day and fun mementos from your journey on the water are available for purchase.
  • Special Events. Watch the Blue Angels, Fireworks, Wednesday Night Races, live music…and more…on board a Watermark yacht. Every year we offer fun Special Events and we’re always adding something new!