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Where to stay in Annapolis
Annapolis is defined by its colonial-era grid radiating from the State House and Church Circle down to the Chesapeake Bay. Staying centrally keeps you within the historic core, where narrow brick sidewalks and steep hills define movement. As you venture toward the Naval Academy or the commercial districts near West Street, the pace shifts from dense maritime history to modern Annapolis life. Choosing your base depends entirely on whether you prefer waterfront proximity or local convenience.
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This area puts you inside the original colonial street plan. Walking cobblestone paths along Prince George or Maryland Avenue brings you directly to the Maryland State House and the busy docks at City Dock. You are perfectly positioned to walk to the Naval Academy gate, upscale boutiques, and waterfront crab houses without ever needing a car once you arrive.
West Street Corridor
West Street serves as the city's modern cultural backbone. It is highly walkable, featuring numerous restaurants, the Rams Head On Stage venue, and the Annapolis Arts District murals. You are about a fifteen-minute stroll from the harbor, allowing for easy access to the historic center while enjoying a more local, less tourist-saturated atmosphere during the evening hours.
Eastport
Eastport feels like a distinct village focused on boatyards and marinas. It is highly walkable to local pubs, casual seafood spots, and scenic parks along Back Creek. The Eastport Bridge provides a pedestrian connection to downtown, though it is a longer walk. It is the best choice for those who want a quieter, residential waterfront vibe away from the downtown crowds.
One thing to think about
Avoid staying near the commercial strip of Forest Drive if you value a walkable vacation. While it offers more parking, it is dominated by heavy traffic and chain stores that require a car to reach any of the historic charm or water-access points that define the city.
Once you have a bed
The things that sell out first in Annapolis are the small-group tours and the skip-the-line tickets.
Top tours & activities
Common questions
Do I need a rental car while staying in Annapolis?
If you stay within the Historic District or Eastport, you do not need a car; the town is exceptionally pedestrian-friendly. However, if your accommodation is near West Street or further out, a car helps with reaching suburban shopping centers or grocery stores. Parking downtown is limited and expensive, so choosing a central location is worth the cost.
What is the best way to get to Annapolis from the airport?
BWI is the closest major airport, approximately 30 minutes away. There is no direct light rail service to the city center. You will need to rely on pre-booked shuttle services, private ride-shares, or rental cars. Plan for traffic during weekday rush hours, as the highway approaches can become significantly congested near the Severn River bridge.
When is the best time of year to visit?
Late spring and early autumn offer the most comfortable weather for walking the city's steep hills and narrow alleys. Summers are humid and crowded with boaters, while winter can be quiet and quite cold near the water. For a balance of pleasant walking temperatures and access to outdoor dining, aim for May or September.
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