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If you're flying into the Baltimore or DC airports, you will hire a taxi or rental car to finish the trip to Annapolis. Once you arrive in the city, your best bet is to take one of two free shuttles from the Navy Marine Corp Memorial Stadium to your Annapolis destination, as the city's streets are reflective of their 18th century design: narrow and with insufficient accomodation for large volumes of traffic.
The city does have some metered parking, with time limits of two hours. The meters are doggedly patrolled by parking enforcement officers and fines are levied for delinquent meters. There are also several parking garages around town, some of which fill up rather fast. Parking is very limited in the downtown historic district. So, whether you park at the stadium and use the shutte, or find a garage, be prepared to do a fair amount of walking. It's good for you, anyway. Here's a walking tour of Annapolis to make your pedestrian endeavors worthwhile.
Annapolis, Maryland, is a city of taxis, with over 160 affiliates registered with the Department of Transportation, so if the thought of much walking deters you, hail a cab. Or put on your floaties and hop onto a water taxi at the city dock of Annapolis Harbor. The water taxi service also offers tours and special events-related services for boat shows, races, and have you ever watched 4th of July fireworks from the water? There's nothing like it.
The Annapolis bus service has five routes within town and the base fare for getting around Annapolis is a mere .75 cents. A trolley has been in operation in the city since 1998.