Fishing & Crabbing

LoosenUp Charter Fishing

Maryland Chesapeake Bay Fishing ChartersLicensed for up to 44 passengers Departs out of Deale, Maryland, only a short distance out of Annapolis and Chesapeake Beach, Maryland. Fishing for Maryland St...

Boating

LoosenUp Charter Fishing

Maryland Chesapeake Bay Fishing ChartersLicensed for up to 44 passengers Departs out of Deale, Maryland, only a short distance out of Annapolis and Chesapeake Beach, Maryland. Fishing for Maryland St...

Tours

Mission Escape Rooms

They'll pay a fee to enter and will be given clues on how to get out. The staff, which will include two to three people, will watch from two-way cameras. Mission Escape Rooms is a new, interactive, f...

Galleries

Nancy Hammond Editions

Nancy Hammond is a painter who loves water life. Living waterside, she takes note of all things Chesapeake. Design is the added element in Hammond’s work which brings it a contemporary tone. Favored...

Attractions

National Sailing Hall of Fame

The National Sailing Hall of Fame is a not-for-profit educational institution dedicated to preserving America's sailing legacy....

Boating

Rob Wagner Charters, LLC

We offer day and over night crewed charters. Come join us and enjoy a special time sailing the Chesapeake. Our 38-foot sailing catamaran, the Alana McCree, is available for crewed charters out of Libe...

Tours

Terrapin Adventures

Terrapin Adventures (TA) operates unique outdoor adventure centers appealing to corporate groups, tourists and more! For a day of teambuilding and fun, visit our onsite center located in Central Maryl...

Kayaking & Paddleboarding

Terrapin Adventures

Come join us as we explore the many waterways of the area. We meet at our kayak put in (call us for directions). Many local rivers and lakes with interesting nooks and crannies are just 30 minutes awa...

Boating

Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Che...

Tours

Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, as well as longer specialty cruises. Sail past the US Naval ...

Events & Festivals

Annapolis Spring Sailboat Show

For three days in April, the Chesapeake Bay's thriving marine industry will relocate to City Dock. From sailboats to sails, from St. Michael's to Main Street, the region's favorite retailers exhibit a...

Tours

Annapolis Tours by Watermark

Journey into history, culture, and fun year round; enjoy an unforgettable walking tour through historic Annapolis with period dressed guides. Tour the Maryland State House, the grounds of the United S...