Embark on Your Unforgettable Journey

Watermark immerses you in the history, culture, and fun of the Chesapeake Bay area more completely than any other tour or charter company.

Cruises & Tours in Annapolis & Baltimore

Unforgettable journeys start with Watermark, and we’ve been doing it for more than 50 years.

Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips.

Annapolis Boat Tours
Baltimore Sightseeing Cruise
Rock the Harbor with Tranzfusion
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Why Watermark?

Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.

  • A complete Annapolis and Baltimore experience
  • Informative and fun, knowledgeable and helpful
  • The most refreshing way to see the sights
  • Unique educational field trips on land and water
  • The most affordable way to get out on the water
  • Meticulously maintained classic and elegant yachts
  • Customized private yacht charters
  • History comes alive in our museum without walls
  • Family fun activities for all ages
  • Highly trained, certified guides, captains, and crews
  • Over 50 years of sharing the best of the Chesapeake

What’s Happening at Watermark

Looking for things to do in Annapolis and Baltimore? It is always a great time to experience Watermark.
Stay connected with the Watermark community.

Check us out on Instagram

Cheers to the weekend 😁🍻 ...

Join your period-attired guide tomorrow afternoon for an African American Heritage Tour offered in partnership with the Kunta Kinte-Alex Haley Foundation and named a “Heritage Award Winner” by the Chesapeake Crossroads Heritage Area.

Saturday 4/20 1:00pm-3:00pm
Meets at Market House Park

🎟️ watermarkjourney.com/events/african-american-heritage-tour/ 🎟️

Pssst Mother`s Day is a month away 👀 Have you made plans yet?

Treat the moms in your life to a lovely brunch cruise!
🌸 Brunch buffet by @PalatePleasers
🌸 Open mom-osa and champagne bar
🌸 Live music by @GuavaJellyMusic

🎟️ Click the link in our bio for tickets 🎟️

Or, moms, send this to someone and drop a (not so) subtle hint 😉

Watching the #TotalSolarEclipse the Annapolis way 👉 On a boat 😎🚢 ...

Guest Journeys

Creating unforgettable journeys for over 50 years.