International Association of Tour Directors & Guides

Annapolis Familiarization Tour

November 21, 2025

Welcome to Annapolis and Anne Arundel County

In case the 500 miles of shoreline and beautiful sunshine didn't give it away, welcome to America's Sailing Capital! Annapolis isn’t just Maryland’s state capital; it’s home to the iconic U.S. Naval Academy and your front door to the easygoing charm of the Chesapeake Bay. Experience waterfront adventures, the freshest seafood you’ll ever taste, and cobblestone strolls through 18th-century charm where adventure is always just around the corner.

What to Know Before You Drop Anchor

• Annapolis and Anne Arundel County sit in central Maryland, perfectly placed between Baltimore and D.C.
• We’re home to the iconic Chesapeake Bay and the Chesapeake Bay Bridge
• Only 30 minutes from Washington, D.C. and Baltimore
• Beyond Annapolis, the county is full of lively suburbs, nightlife, and year-round entertainment
• Baltimore/Washington International Thurgood Marshall (BWI) Airport is just 25 minutes from downtown Annapolis
• From historic landmarks to local art scenes, the area blends past and present beautifully
• If you’re into fresh crab, oysters, and Old Bay on everything, you’re in the right place

This is Where Adventure Begins

• Start your exploration of Annapolis: Museum Without Walls™ at the William Paca House and Garden, a five-part Georgian mansion built in the 1760s for William Paca, one of Maryland’s four Signers of the Declaration of Independence and the state’s third Governor.
• The Hogshead at 43 Pinkney Street, an early 18th-century building reminiscent of the modest wood-frame homes that once housed colonial Annapolitans and revolutionary recruits, now serves as an interactive museum where visitors can experience daily life in 1700s Annapolis.
• Unleash your inner explorer at the Annapolis Maritime Museum, where the Chesapeake Bay’s story comes alive through historic vessels, immersive VR, and hands-on exhibits that blend history, tech, and fun for all ages.
• Explore the U.S. Naval Academy, the undergraduate college of our country’s naval service. The Academy trains midshipmen to graduate as Navy ensigns or Marine Corps second lieutenants, while developing competence, character, and compassion. Walk the hallowed halls surrounding John Paul Jones’ crypt and The Chapel.