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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...

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 ...

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...

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...

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 ...

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 ...

Historic Ghost Walks

As the sun sets and darkness descends upon the timeless streets of Annapolis, follow your spirit guide who will share stories of drowned watermen and other spirits that forever linger in the mist. Ann...

James Brice House

The James Brice House is one of the largest and most elegant of Annapolis' historic mansions. Construction on thie five-part Georgian home started in 1767 after the death of James' father, Judge Brice...

Navy Yard Tour with Annapolis Tours

Explore the yard of the United States Naval Academy with a certified USNA tour guide from Annapolis Tours by Watermark. Watermark's Four Centuries Walking Tour (offered daily March-October and Saturda...

Urban EvenTours

Urban EvenTours offers a fun, intimate & unique way to see Annapolis and its surrounding neighborhoods like a local!  In fact many of our travelers are locals - seeing their own city in a different w...

Colonial Tours of Annapolis

Whether making a day trip to Annapolis, vacationing in the area, or living here, a walking tour of Annapolis is the best way to really experience the people and places from over 200 years ago. Annapol...

Cruise Maryland from the Port of Baltimore

Cruise Maryland offers year round cruising to the Bahamas, Bermuda, Canada/New England and the Caribbean on Carnival Cruise Lines Pride and Royal Caribbean International's Grandeur of the Seas. In 201...