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.

When the company first started, it put all the paid bills in a shoe box and hand the box to the accountant at the end of the year. There were no full-time employees and about 10 seasonal ones. Now it has an accounting system, controller, email, multiple websites, online ticketing, payroll service, five department heads, and four offices. The company employs 18 full-time and 160 seasonal workers. 

Today the company is in its second generation of family ownership with Hartman's daughter Debbie Gosselin at the helm. Watermark offers private charters, an Annapolis water taxi service, a variety of walking tours, public cruises in Annapolis and Baltimore and special event tours and cruises.
 
It recently added a second excursion boat in Baltimore, the 149-passenger Raven that was docked in response to the city's request for proposal for an iconic boat in the Inner Harbor. Raven offers private yacht charters for birthdays, corporate events, anniversaries, weddings and special events.