To hit the high points in town, take a Historic Annapolis Walk. Visitors carry digital audio wands, which are customizable to enable you to go to places of the most personal interest. Tours focus on African-American Heritage, the Civil War, and the Revolution. They're available only at the Historic Annapolis Foundation's Museum Store, 77 Main St. (tel. 410/268-5576; www.annapolis.org), Tuesday through Saturday from 10am to 6pm, Sunday from 11am to 6pm. The tours last about 2 hours.
Annapolis Tours (tel. 410/268-7601; www.annapolis-tours.com) are led by guides in Colonial costume. Tours of the historic district, which include the Naval Academy, last 2 hours and don't require reservations. From April through October, they depart daily at 10:30am from the visitor center at 26 West St. and at 1:30pm from the City Dock information booth. (If you take a morning tour, guides try to get you to the Naval Academy in time for the midshipmen's noon formation.) From November through March, there is only one tour a week, Saturday at 1:30pm, departing from the City Dock information booth. The price is $11 for adults and $6 for children 17 and under. (Note: Picture ID is required for those 18 and older to gain access to the Naval Academy and State House.) Other options include ghost tours on October evenings and candlelight strolls on December evenings; check the website for a schedule.
Naval Academy Walking Tours depart from the Armel-Leftwich Visitor Center of the United States Naval Academy at Gate 1 on King George and Randall streets (tel. 410/263-6933; www.usna.edu) daily except Thanksgiving, Christmas, and New Year's Day. In July and August, tours depart every half-hour. From September through November and April through June, tours depart every hour Monday through Friday, and every half-hour Saturday and Sunday. From December through March, tours are offered as needed. The schedule varies a lot, so call ahead or check the website before coming -- or sign up when you get to the visitor center. The price is $9 for adults, $8 for seniors, and $7 for students. Bring picture ID.
Capital City Colonials (tel. 410/295-9715; www.capitalcitycolonials.com) offers "Annapolis in an Hour" tours for $10, as well as other historical tours. Combine food with history on the 11am tours, which include some time to rest as well as eat over a 3-hour period. They cost $42 and are scheduled Thursday through Saturday at 11am and Sunday at 1pm. Reservations are recommended.
Tours by Bus, Trolley, Carriage & Segway
Discover Annapolis Tours, 31 Decatur Ave. (tel. 410/626-6000; www.discover-annapolis.com), offers 1-hour trolley or minibus tours of the city and outlying areas. An air-conditioned 25-passenger trolley takes visitors through the historic district -- by the State House, Chase-Lloyd House, Hammond-Harwood House, and St. John's College, to name a few -- and areas not covered by the walking tours: Eastport, the Charles Carroll House, and the Severn River Scenic Overlook. Tours operate daily April through November, departing from the lot behind the visitor center at 26 West St. Saturday tours are available December through March. The cost is $18 for adults, $9 for children 11 to 15, and $3 for children 10 and under (free for preschoolers). A 40-minute tour is also available, leaving from HistoryQuest, 99 Main St.
Watermark Tours (tel. 410/268-7601, www.watermarkcruises.com) offers "Four Centuries" walking tours daily April through September and Saturdays October to March. Tickets are $16 for adults, $10 for ages 3 through 11. They include the historic district and Naval Academy. Photo ID is required; reservations necessary. Watermark also offers African American Heritage tours through February and Saturdays May through October, ghost tours in October, and candlelight in December. Tickets are $14 for adults, $7 for children 3 to 11.
Annapolis Carriage (tel. 800/639-9153; www.annapoliscarriage.com) offers 20-minute carriage rides throughout the day. The coachman points out areas of interest and gives a brief history for up to four riders (six with kids). Reserve online, by phone, or in person at HistoryQuest, 99 Main St. (tel. 410/267-6656; www.reservations.annapolis.org). Tours cost $35 for adults, $15 for children. Private tours are available. Hours vary by season; check the website for a schedule.
Segs in the City, 42 Randall St. (tel. 800/SEGS-393 [734-7393]; www.segsinthecity.net), enables visitors to explore the historic district on two-wheel Segways. Guided 1- or 2-hour tours cost $45 to $70. Trained riders can rent Segways for $50 to $150.
Cruises & Boat Tours
Watermark Cruises, at the City Dock (tel. 410/268-7600; www.watermarkcruises.com), offers excursions along Annapolis Harbor and beyond. Choices include a 40-minute kid-friendly narrated cruise aboard the Harbor Queen that covers the highlights of Annapolis Harbor, the U.S. Naval Academy, and the Severn River; a 40-minute tour aboard the Miss Anne of the Eastport waterfront along Spa Creek and the Naval Academy shore; a 90-minute Thomas Point Lighthouse Cruise on the Severn River; and a Day-on-the-Bay excursion to St. Michaels. The Lady Sarah offers bay lighthouse cruises. In summer, catch a ride on a pirate ship. Prices range from $12 to $40 for adults, $5 to $10 for children 3 to 11. Sailings are daily from Memorial Day to Labor Day, with abbreviated schedules in spring and fall.
Pirate tours seem to be all the rage and you can find them in Eastport. Pirate Adventures, 311 Third St. (tel. 410/263-0002) goes out six times a day at the height of the season. Cruises aimed at 2- to 9-year-olds last 75 minutes. Kids get "tattoos," wear pirate clothes, find treasure, and engage in water-gun battles. Reservations for weekend cruises are recommended. Tickets are $18.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.