Tours

Annapolis Helicopter Tours: Monumental Helicopters

Join us for a helicopter tour of Annapolis, Baltimore, OR Annapolis AND Baltimore in one ride! Offering custom tours, corporate events, romantic sunset flights, and family entertainment. We have a 100...

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 ...

Performing Arts

Annapolis Shakespeare Company

Annapolis Shakespeare Company is a regional theatre company offering over 200 live performances annually. The Baltimore Sun recently referred to Annapolis Shakespeare Company as part of the “increas...

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...

Boating

Cruises on the Bay by Watermark

Cruises on the Bay by Watermark has been offering sightseeing cruises to visitors and residents of Annapolis for over 40 years! Cruises run daily through early Spring until early Fall with Special Eve...

Tours

Discover Annapolis Tours - 40 Minute Tour

Two Trolley Tours available - 40 minutes or 60 minutes: Our 40 minute tour offers "A little about a lot!" Sit back and relax as we get away from the waterfront to explore the back streets of Annapoli...

Tours

Discover Annapolis Tours - 60 Minute Tour

Our 60 minute tours start and end at the Annapolis Visitor's Center, located at 26 West St. There are about 1300 buildings in Annapolis at least a century old, representing 15 different architectural ...

Tours

Four Rivers - Heritage Area of Annapolis, London Town & South County

Four Rivers: The Heritage Area of Annapolis, London Town & South County offers an extraordinary wealth of historic, cultural, and natural resources to visitors and residents alike. Experience a place ...

Events & Festivals

Four Rivers - Heritage Area of Annapolis, London Town & South County

Four Rivers: The Heritage Area of Annapolis, London Town & South County offers an extraordinary wealth of historic, cultural, and natural resources to visitors and residents alike. Experience a place ...

Museums

Historic Annapolis Museum

The Historic Annapolis Museum is located on the 2nd and 3rd floor of the three-story structure located at 99 Main St. This site was built in the 1790s, on the site of earlier buildings that had burned...