Graduate by Hilton Annapolis

Offering immaculate customer service and responsiveness, the team at Thoroughbred is available and ready to assist you in all your event, business, and personal transport needs. Priding themselves in reliability and availability, Thoroughbred is always there to get you from Point A to Point B. Thoroughbred Sedan, Van & Bus was founded by transportation veteran Joe Rosensweet, who serves as the driving force behind this business. Joe has combined his experience, expertise, knowledge and understanding of what an elite personal transportation service requires and brought it to the forefront of this industry. Joe has taken these characteristics and added his engaging personality as well as his personal touch to create a transportation experience that is worry-free for each client. Joe’s engaging personality and hard work-ethic allows you to Ride Thoroughbred with confidence, every time. We are committed to creating customized and competitive rates for your personal and corporate transportation needs.

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, 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. 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.