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 and 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.

This Week's Cruises & Tours

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Why Watermark?

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

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Who`s excited for the weekend? This guy 😆 ...

Discover Annapolis history with a twist 🧐🌀

Join your colonial-attired guide this Saturday afternoon to learn the weird, wacky, and unusual history of Annapolis.

Hear tales about the Russian sailor buried in the Annapolis National Cemetery, the historic “mobile homes” of Annapolis, the Confederate captain who kept fighting the Civil War long after the South surrendered and then built a home in Annapolis, the missing State House cornerstone … and so much more!

Saturday, July 13th 10:30am from 188 Main Street

🎟️ https://watermarkjourney.com/events/weird-wacky-unusual-history-of-annapolis-tour/ 🎟️

Meet the Team: Captain Aaron Hull ⚓️ ...

What a great holiday week! Thank you to our tour guides for bringing their colonial flair and representing Watermark in the Annapolis 4th of July parade 😁🇺🇸🎇 ...

Happy 4th of July 🚢🇺🇸🎇 ...

Meet the Team: Suzy Elcik 🌊 ...

Meet Mistress Susannah! 😁 ...

Watermark Staff over the last 50 Years

Watermark Team Since 1972

A family-owned business since 1972. Learn more about the growth and progression of Watermark.

Our Watermark Team Today

Interested in joining the Watermark family? Get to know our team here and view our open positions.

Guest Journeys

Creating unforgettable journeys for over 50 years.