Sightseeing Boat Cruises in Annapolis Maryland
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| Annapolis Tours by Watermark ® |
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| Don't forget to check out our Annapolis walking tours. |
| Annapolis Cruise Video |
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| Watermark Video |
| Baltimore Inner Harbor Cruises |
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| Inner Harbor Cruises 45-minute Cruises of Baltimore Inner Harbor |
Cruise and Explore the Chesapeake Bay
Annapolis Harbor · USNA Boat Tour· Chesapeake Bay Lighthouse Cruise· Kid's Pirates Cruise · Music Cruise
Looking for things to do in Annapolis?
Come explore 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 family activities or a romantic outing with a loved one, Watermark has the perfect cruise for you!
Cruises are pet-friendly as long as they are friendly and leashed.
Click here to book the Santa Maria Cup Cruise!
| 40 Minute Cruise | 90 Minute Cruises | Jolly Express Cruise |
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| An introduction to Annapolis and U.S. Naval Academy (details). | Explore the treasures of the Chesapeake Bay (details). | Celebrate the Holidays! (details). |
| Bay Lighthouses Cruise | Day on the Bay in St. Michaels | Music Cruises |
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| Featuring a historical turn of the century keeper (details). | The perfect way to spend the day (details). | Music cruises with WRNR (details). |
Any event may be canceled due to severe weather, lack of participation or mechanical breakdown.
