Welcome to Watermark


Watermark’s vision since the beginning has been to immerse people in the history, culture and fun of the Annapolis area more completely than any other tour or charter company. Whether you want to learn or just enjoy, 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. In fact, we originated the idea of giving our guests a truly authentic Annapolis experience 40 years ago. And our unique training program ensures that everyone in the company — from period-dressed tour guides to captains to Event Planners — shares that experience in the most interesting and exciting way.


Watermark, originally Chesapeake Marine Tours, began by offering a single sightseeing cruise to St. Michaels aboard the Annapolitan in 1972. Founder Ed Hartman, an attorney by trade, had a love of boating and a desire to invest in the local community. The company quickly expanded to include scenic narrated cruises of the Annapolis Harbor on Harbor Queen and private yacht charters.

Today in its second generation of family ownership with Hartman's daughter Debbie Gosselin at the helm, Watermark's range of offerings includes endless possibilities for private charters with Yacht Charters on the Bay™ and Wedding on the Bay™, Annapolis water taxi service, a variety of walking tours with Annapolis Tours®, public cruises in Annapolis and Baltimore with Cruises on the Bay™ and special event tours and cruises throughout the year.


Watermark has the largest private fleet of luxury yachts on the Chesapeake Bay. Our yachts are the perfect venue for board meetings, award ceremonies, holiday parties, wedding receptions and other celebrations in the Annapolis and Baltimore area. We make planning easy and events run flawlessly.

Yacht charters can depart from various ports including popular destinations in Baltimore, Annapolis, and Maryland’s Eastern Shore. Our boats can accommodate 2 guests up to 280 and bookings can be for less than an hour to an all day cruise. We work with the area's premier vendors to offer a variety of menu and bar options, decor and more

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