Watermark Tours Charters Cruises

Watermark Tours Charters Cruises Watermark® an Annapolis-based, locally owned and operated business, has been creating authentic experiences since 1972.
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Watermark® has immersed people in the history, culture, and fun of the Chesapeake area more completely than any other tour or charter company for more than 50 years. Whether you want to learn or just enjoy the Chesapeake Bay area, no one else offers so many ways to experience this special place, both by land and by water, in less than an hour or as long as you like. Offering historic walking tours, cruises, and special events for individuals and groups in both Annapolis and Baltimore.

09/02/2026

From ticket sales to captain, Bryan Harris has done it all! We’re glad to have him part of our crew. You could say it’s in his blood! 😉

08/20/2026

🚨 ATTENTION! ATTENTION! 🚨

Watermark has a new addition to the family! Meet Queenie, our new Watermark mascot, modeled after the Annapolis icon, Harbor Queen! 👑⚓️ We’re so excited to welcome her aboard! 💙

Now, we want YOU to join in the fun! 🎉

To celebrate Harbor Queen’s legacy and introduce Queenie to the community, we’re inviting you to:

📸 Snap a photo with Queenie
📱 Post it on social media
🏷️ Tag and use

For a chance to win a family four-pack aboard Harbor Queen, including four drink tickets and four popcorn vouchers! 🍿🥤

Get creative, have fun, and show us how you’re welcoming Queenie to the Watermark family! 👑💙

🌊 Set sail from Annapolis and experience the Chesapeake like never before! Join our live interpreter for a relaxing 3-ho...
08/18/2026

🌊 Set sail from Annapolis and experience the Chesapeake like never before! Join our live interpreter for a relaxing 3-hour cruise through historic Annapolis Harbor, along the scenic Severn River, and out onto the Chesapeake Bay. Cruise beneath the iconic Bay Bridge and journey to the beautiful Thomas Point Lighthouse. ⛵️🌅

Bring your camera, sit back, and enjoy the views, stories, and history along the way!
Get your tickets here: https://watermarkjourney.com/events/chesapeake-bay-trio-river-lighthouse-bridge/

We’re rocking the harbor again this Friday! 🎶🌅 Join Michael Miller aboard the Harbor Queen for an unforgettable evening ...
08/13/2026

We’re rocking the harbor again this Friday! 🎶🌅 Join Michael Miller aboard the Harbor Queen for an unforgettable evening of live music, breathtaking sunset views, and all-around good vibes.

Grab your tickets for Watermark’s Friday Night Live Sunset Music Cruise Series and start your weekend the best way possible—on the water! 🚤✨ https://watermarkjourney.com/events/annapolis-sunset-cruise-with-live-music/

08/10/2026

Ghosts, pirates, and a bar. 👻🍺

Walk the Historic District with a Ghost Guide, then cruise the haunted harbor for pirate tales and nautical legends. Drinks available on the boat. See you on Friday.

08/05/2026

One Harbor Queen takes you on the water. The other takes care of lunch. 😋

The Big Cheese Harbor Queen sandwich is named after one of Annapolis’ most iconic boats, and since they’re only two blocks apart, it’s the perfect stop before or after your cruise.

Address

1 Prince George Street
Annapolis, MD
21401

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