St. Mary's Parish

Sail away on the Chesapeake Bay! We have two, 74-foot schooners that sail out of downtown Annapolis up to four times daily on public sailing cruises. Come aboard and sit back and relax with a cold beverage. We have a bar with fantastic independent, craft brews from the local area. All public cruises come with a complimentary soft drink or water. Want the boat all to yourself? We also specialize in private events with catering. From corporate cruises to team building events, birthdays to reunions, schmooze cruises to incentive "sails", we can do them all. Students, scouts and group sails are another educational and interactive cruise that we offer.

Our 18th century Ballroom is located upstairs and boasts a private cocktail area, private bathrooms and an optional private VIP room. It can seat up to 100 guests in a formal seating arrangement *theater style & cocktail style can accommodate larger groups. This is a legendary Annapolis Banquet Hall. Audio & AV equipment, signage, event props & corporate gifts available upon request

Coodman Building, 100 Main St

Watermark® immerses people in the history, culture and fun of the Chesapeake Bay region. Choose from our wide array of offerings on land and sea: walking tours, sightseeing cruises, group tours, private yacht charters, event venue space, field trips, and more. Our tours and cruises are a unique and fun option when looking for things to do in Annapolis and Baltimore.

Continental breakfast & parking are included at this charming, 3-townhouse lodging with a garden.

Elegant rooms with period-style decor in 3 historic inns, plus an English-style pub & a gym.

Chart House Prime is a Maryland treasure through and through. Like its menu filled with local ingredients, part of Chart House Prime's appeal comes from its position in the community. Formerly a historic boat house that was the primary shipyard for John Trumpy & Sons, Chart House Prime seafood restaurant provides stunning views of Spa Creek. And a million dollar remodel sets Chart House Prime apart from the competition. Our journey began in 1978, when our Chart House Prime waterfront location in Annapolis opened its doors to provide customers with a dining experience beyond the cuisine. Today, we continue to build on that legacy with Chart House Prime. Our focus remains using the finest ingredients to bring you the best in refined seafoo...

Annapolis