Watermark Flag

About Us

Welcome to Watermark!

Our Promise

Watermark immerses people in the history, culture and fun of the Chesapeake area more completely than any 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 Chesapeake experience over fifty years ago. And our unique training program ensures that everyone in the company, from period-dressed tour guides to captains to event planners, are still the people that share that experience in the most interesting and exciting way.

Rainbows can be seen from the deck of Lady Sarah



Watermark, originally Chesapeake Marine Tours, was founded by C. Edward Hartman II. Mr. Hartman, an attorney by trade, had a love of boating and desire to invest in the local community. Chesapeake Marine Tours began by offering a single sightseeing cruise to St. Michael’s aboard Annapolitan in 1972. That Day on the Bay cruise is still offered today. The company’s offerings expanded quickly to include 40-minute cruises of the Annapolis Harbor and the U.S Naval Academy shoreline as well as private charter service. The fleet inevitably grew; first, in 1973 the Annapolis landmark Harbor Queen was added. During the 1980s both Miss Anne and Miss Anne II were added and began providing tours of Spa Creek as they continue to do today. Over the years the fleet has changed; additions that remain today include Annapolitan II, Cabaret II in 1996, followed by Catherine Marie in 1999, Lady Sarah in 2005 and the most recent addition Raven in 2012.

Watermark has been providing Water Taxi service in the harbor since the 1980s. Watermark presently has four modified Privateer hulls serving as taxis in the Annapolis Harbor, Eastport, Spa Creek and Back Creek. Locals and visitors alike find the Water Taxi a convenient, affordable and enjoyable way to journey across the Harbor.

Harbor Queen 1970


Watermark Crew

harbor queen


Growth & Progression

In 1999 Ed Hartman’s daughter, Debbie Gosselin purchased Watermark from her father. Having worked for the company since 1982, Ms. Gosselin had a vision of expanding and diversifying the public sightseeing cruises offered on the Chesapeake Bay and continuing the commitment to excellence in private charter service.

Over the years, Watermark established itself as the central resource for locals, visitors, school groups, social groups and corporate clients alike. School groups, in particular, became familiar with Watermark as thousands of school-aged children stepped aboard Harbor Queen each year for their annual field-trip to Annapolis, Maryland. As a result of the many field trip opportunities, Watermark established a partnership early on with another Annapolis business, Three Centuries Tours.

Founded in 1975 by Paula Fishback, Three Centuries Tours was created to provide more ways for people to learn and experience the rich history and heritage of Annapolis, Maryland. In 1979, Ms. Fishback introduced authentic colonial attire for all of her walking tour guides. The period dress proved to be a significant distinguishing selling point for the young company. After many years of working together to provide unforgettable land and water experiences, Chesapeake Marine Tours purchased Three Centuries Tours in 2004, creating Watermark, the provider of the complete Chesapeake Bay experience as it is known today.

On the water, Watermark expanded its sightseeing cruise and private charter offerings to the Baltimore Inner Harbor in 2009. Watermark’s tour guides are also available for step-on guide and concierge services in Baltimore city.

In 2022, Gosselin retired, selling Watermark to the company’s General Manager of Vessel Activities and lifelong family friend Jake Iversen and his wife Laura.


Watermark’s range of offerings includes endless possibilities for private yacht charters, water taxi service, historical walking tours, ghost tours, a variety of public cruise options and special events. Longtime favorites like the company’s Harbor Queen cruises, Four Centuries Walking Tour and Baltimore Harbor Cruises on Annapolitan II stand side by side with newly developed experiences each season. Watermark is a leader in the regional hospitality industry and has many partnerships in the surrounding community. The company’s goal is to provide uncompromised customer service during an authentic Chesapeake Bay experience and to maintaining deep involvement in the local business community and charitable efforts.

Mayor & Raven



  • Best Rehearsal Dinner/Welcome Party Venue for What’s Up? Media’s Best of Weddings – 2024
  • Don Riddle Corporate Citizenship Award from the Anne Arundel Chamber of Commerce – 2023
  • Small Business of Year from the Maryland Tourism Coalition – 2021
  • Best of Retail and Professional Services from What’s Up? Annapolis – 2018
  • Heritage Partnership Award from Four Rivers Heritage Area for Architrex. For Partnership with Historic Annapolis – 2018
  • Youth Group Manager Claudette McDonald awarded Audrey Davenport Hospitality Person of the Year Award by the Maryland Tourism Coalition – 2018
  • Heritage Partnership Award from Four Rivers Heritage Area for Architrex. For Partnership with Historic Annapolis – 2016
  • Tourism Partnership Award from Maryland State Tourism Council for Architrex. For Partnership with Historic Annapolis – 2016
  • Group Sales Manager Jennifer DeLancey awarded “New Professional of the Year” by the Maryland Tourism Coalition – 2014
  • Director of Land Operations Heather Skipper awarded “Heritage Professional of the Year” by Four Rivers: The Heritage Area of Annapolis, London Town & South County – 2014
  • United States Coast Guard Awards for Inspection Excellence – 2014
  • Best Website Award for AnnapolisTours.com by the Maryland Tourism Coalition – 2013
  • Tour Guide & Annapolis Towne Crier Frederick Taylor awarded Interpreter of the Year by Four Rivers: The Heritage Area of Annapolis, London Town & South County – 2013
  • Public/Private Initiative Award for partnership with United States Naval Academy to develop the War of 1812 walking tour: Seas, Lakes & Bay by Four Rivers: The Heritage Area of Annapolis, London Town & South County – 2012
  • Harbor Queen Campaign awarded for Continuing Campaign Promotion by Maryland Tourism Coalition – 2011
  • Director of Land Operations Heather Skipper awarded Maryland Tourism Education Foundation award for Educational Development – 2011
  • President Debbie Gosselin awarded Person of the Year by Maryland Tourism Coalition – 2010
  • Tour Guide Mistress Meg Govan awarded Interpreter of the Year by Four Rivers: The Heritage Area of Annapolis, London Town & South County – 2010
  • Company Security Officer Captain Dean Scarborough awarded Roger Murphy National Safety Award by Passenger Vessel Association – 2009