Welcome to Watermark!
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.
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.
- 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