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Annapolis & the Chesapeake Bay - Official Destination Marketing Organization for Annapolis & Chesapeake Bay

Evening Suggestions

Annapolis Ghost Tours

Got Ghosts? We do! And we’ll tell you all about them…who they are, where they haunt, why they’re still here! Allow Annapolis Ghost Tour's guides to take you on a lantern-led ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history, while meeting some of our more spirited residents and visiting our most horrific haunted sites! Tour lasts approximately 90 minutes..

Medieval Times Dinner and Tournament

An exciting adventure back to the Middle Ages set inside an 11th-century-style castle. Feast on a four-course meal while watching spectacular pageantry, exquisite horsemanship and an authentic medieval jousting tournament. Medieval Times Dinner and Tournament will provide an unforgettable evening for your group. Plan to spend 3 hours to receive royal treatment!

Schooner Cruises

Consider a sunset or evening cruise aboard one of our magnificent schooners. Annapolis is home to the Schooner Woodwind I; the Schooner Woodwind II; Liberté, the Schooner; and Schooner Imagine…! Your group can raise the sails, steer the boat or just sit back and relax as the ship sails from the historic waterfront, past the Naval Academy and cruises into the Chesapeake Bay. Allow at least 2 hours for the cruise.

Yachts

Entertain in grand style on a beautiful yacht. Call one of our many charter companies and plan a unique special event. From 2 to 290, there is a beautifully appointed luxury yacht waiting to make waves for your next event. Please visit our Attractions section for a list of charter boats. You may also wish to have one of our Destination Management Companies or Corporate and Social Event Planners assist you with the planning. Visit our Event Planning and Support Services section for those listings. Allow at least 3 hours for your cruise.

Haunted Pub Crawls by Annapolis Ghost Tours

For the more daring, take a raucous romp on a Haunted Pub Crawl. Filled with stories of resident ghosts, haunted taverns, and restless spirits, our tours will have you sleeping with one eye open! The pub list may include: Galway Bay, Harry Brownes, Sly Fox Pub at the Reynolds Tavern, The Drummer's Lot at Maryland Inn, Rams Head Tavern, Middletons Tavern, or Phillips Seafood Restaurant. This tour is reserved for adults 21+ only and lasts approximately 2 hours.

Theater

There are great opportunities for your group to enjoy theater or dinner theater. Consider Bay Theater, located in the heart of Annapolis, offering professional theater in an intimate, off-Broadway-style house. The Colonial Players offers exciting live theater year round with comedies, drams, and musicals performed in an intimate 180 seat theater-in-the-round. Professional dinner theater is available at Toby’s –convenient to Annapolis and BWI, offering Braodway musicals, live orchestra, and a seven entrée buffet.

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