Come Sail Away to Annapolis and Anne Arundel County where your family will discover adventures by both land and sea. Take a guided tour by foot or trolley through the city to learn some of its illustrious history and book your family on a pirate cruise of the Chesapeake Bay.

Look below for some must-dos in Annapolis and Anne Arundel County.

Spring and Summer Activities

• Annapolis Carriage Tours/Rides 
• Annapolis Sailing Cruises: Schooner Woodwind
• Annapolis Summer Garden Theatre
• Capital City Colonials
• Discover Annapolis Minibus Tours
• Liberte, The Schooner
• Maritime Heritage Festival
• Pirate Adventures on the Chesapeake
• Sail the Pintita
• Watermark Cruises and Annapolis Tours
• Wednesday Night Races

Fall Activities

• Annapolis Carriage Tours/Rides 
• Annapolis Summer Garden Theatre
• Maryland Renaissance Festival
• Capital City Colonials
• Discover Annapolis Minibus Tours
• Kunta-Kinte Heritage Festival
• Liberte, The Schooner
• Maryland Seafood Festival
• NAVY Sports
• Pirate Adventures on the Chesapeake
• Schooner Woodwind
• Watermark Cruises and Annapolis Tours  

Winter Activities 

• Annapolis Carriage Tours/Rides
• Discover Annapolis Minibus Tours
• Ice skating at Naval Academy
• Lights On The Bay
• NAVY Sports 

Plan Ahead

• Annapolis Sailing School
• Chesapeake Sailing School
• Colonial Players Acting & Directing Classes 
• Maryland Hall Performing Arts Classes

In Historic Annapolis

• Aromi di Italia Gelato
• Annapolis Ice Cream
• Boat Cruises (Watermark and Schooner Woodwind)
• Buddy’s Crabs and Ribs
• Chick and Ruth’s Delly (come for the Pledge of Allegiance each weekday morning at 8:30, weekends, 9:30)
• Playground at the corner of St. Mary’s & Compromise Streets
• The Gov. Calvert House (check out the glass floor in the lobby!)
• The State House
• US Naval Academy  

In Anne Arundel County

• Arundel Mills Shopping
• Arundel Olympic Swim Center
• B&A Hiking and Biking Trail
• County Parks
• Historic London Town (archaeological digs!) 
• Sandy Point State Park
• Westfield Annapolis 

Day Trips

• Baltimore Zoo
• National Aquarium in Baltimore
• Six Flags America