Group Experiences

Annapolis & Baltimore, Maryland

Watermark has the perfect tour for your group event!

Explore Maryland by Land & Sea

Watermark offers a wide variety of group experiences in Maryland. Perfect for family gatherings, social occasions as well as military, educational, religious, and fraternal organizations. With seamless itineraries, affordable options, and knowledgeable representatives, we customize your experience to fit your group’s needs.

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Annapolis, Maryland

Baltimore, Maryland

The Destinations

From narrated sightseeing cruises to guided historic walking tours through the cities’ historic streets, we have many ways to explore the beautiful historic seaports of Annapolis and Baltimore by land and sea.

Annapolis and Baltimore are convenient locations to add to your Mid-Atlantic trip!

Close to major airports

  • 30-minute drive from BWI
  • 1-hour drive from DCA
  • 1½-hour drive from IAD

Close to major cities

  • Less than 1 hour between Annapolis and Baltimore
  • Less than 1 hour from Washington, D.C.
  • Less than 2 hours from Philadelphia
  • Less than 4 hours from New York City

Guided Historic Tours

Explore centuries of history in Annapolis and Baltimore with our period-attired guides.

U.S. Naval Academy

Walk the grounds of the historic U.S. Naval Academy, home to over 4,000 midshipmen.

Harbor Queen

Annapolis Harbor

Discover the historic city of Annapolis with a cruise along the harbor and the banks of the U.S. Naval Academy.

Baltimore Inner Harbor

Enjoy all that Baltimore has to offer, including the iconic Domino Sugar sign, Fort McHenry, and more.

Large group at dock

Extended Cruises

Take in the views and history of these two picturesque cities with a sightseeing cruise. Narration options available.

Expand Your Itinerary

Enjoy both daytime and evening experiences! Our strong network of partners allows us to plan seamless itineraries that fit your needs.

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