Walking tours are a great way to see Annapolis's historic district. HistoryQuest rents two self-guided (with audiotapes and maps) walking tours: "Historic Annapolis Walk with Walter Cronkite" and "Historic Annapolis African-American Heritage Audio Walking Tour." The cost for each is $5. Guides from Three Centuries Tours wear Colonial-style dress and take you to the State House, St. John's College, and the Naval Academy. The cost is $13. Tours depart daily April through October at 10:30 from the visitor center and at 1:30 from the information booth, City Dock. From November through March one tour a week leaves on Saturday at 1:30 from the information booth.
Discover Annapolis Tours leads one-hour narrated minibus tours ($18) that introduce you to the history and architecture of Annapolis. Tours leave from the visitor center daily April through November and most weekends December through March.
From April through November, Discover Annapolis runs 40-minute motorized Historic Annapolis Trolley Tours through the historic district of Annapolis. Sightseeing includes the State House, City Dock, and Colonial and Victorian homes. Tickets are sold at HistoryQuest, at 99 Main Street. Tours leave from the Annapolis Visitor Center at Northwest and Calvert streets. There is paid parking adjacent to the center.
The schooners Woodwind and Woodwind II are twin 74-foot boats that make two to four trips Tuesday through Sunday between April and October, with some overnight trips. Two-hour sails are $31 to $34. When the weather's good, Watermark Journeys runs boat tours that last from 40 minutes to 7½ hours and go as far as St. Michaels on the Eastern Shore, where there's a maritime museum, yachts, dining, and boutiques. Prices range from $10 to $60. Watermark also runs land tours that depart from the information booth at the City Dock. The tours include a 90-minute "Colonial Stroll" and a two-hour "African-American Heritage Tour." Tours run from April through October, and not every tour is given every day. Check the Watermark Journey Web site for information. Prices range from $12 to $16.
If you'd rather see Annapolis from a horse-drawn carriage, board "Annapolis Carriage" at the City Dock outside the Market House. The historic tours last either 25 minutes or 50 minutes and the carriages carry four adults comfortably.