Why Go to Annapolis
YOUR DESTINATION AT A GLANCE
Step into historic Annapolis and you'll feel yourself slow down. Maryland's capital takes its name from Queen Anne, who was on the throne in the early 1700s, and for more than 300 years it has kept its colonial charm, with brick sidewalks, cobblestone lanes and beautifully preserved 18th-century buildings.
Once called the Athens of America, Annapolis has always been rich in history and culture. Tour the Maryland State House, the oldest state capitol still in legislative use and briefly the U.S. capital. Visit the Frederick Douglass Museum and Cultural Center, and stroll the grounds of the U.S. Naval Academy. Then wander down to the busy harbor, known as Ego Alley, to watch the boats, grab fresh Chesapeake Bay crab and soak up the waterfront atmosphere. Millions of visitors come every year, but it still feels like an intimate, walkable port town.
Annapolis is an easy drive from Washington, D.C., and Baltimore, making it a perfect weekend escape or add-on. I'll find you a historic inn near the water and plan the tours and dinners that make it memorable.
BEST FOR
History buffs, sailing fans, couples and seafood lovers
BEST MONTHS
April–June and September–October
EXPLORE
Historic Downtown surrounds Main Street and City Dock; the Naval Academy borders the waterfront; Eastport offers a more local maritime atmosphere.
SIX18 SIGNATURE DESTINATION GUIDE
Annapolis
North America › Mid-Atlantic › USA › Maryland
Sailing traditions and brick-lined colonial streets
Historical & Heritage
Sailing
Navy
Architecture
SIX18 INSIDER TIP
Colonial streets, Chesapeake sailing culture and the Naval Academy create a relaxed waterside city trip.
Experiences Worth Exploring
THINGS TO DO
Public entry is controlled; check identification requirements and tour availability before arriving.
United States Naval Academy
Explore the U.S. Naval Academy’s historic campus and learn about naval officer training and traditions.
Check legislative sessions, security procedures and public tour access.
Maryland State House
Visit the nation’s oldest state capitol still in continuous legislative use, with chambers and exhibits on Maryland government.
Parking can be scarce; explore surrounding streets on foot.
City Dock
Watch working boats and harbor activity at the historic waterfront gathering place near downtown Annapolis.
Confirm guided-tour availability and separate garden access arrangements.
William Paca House and Garden
Tour a Georgian-era mansion and formal garden associated with Maryland signer William Paca.
Check the museum’s current location, exhibition calendar and waterfront programming.
Annapolis Maritime Museum
Learn about Chesapeake Bay maritime traditions, oyster harvesting and Annapolis waterfront life through exhibits.
A waterfront property overlooking Annapolis Harbor, well suited to travelers who want immediate access to City Dock, boat outings and the historic district. Compare room views, parking arrangements and waterfront activity before booking.
Annapolis Waterfront Hotel, Autograph Collection
Historic Waterfront
City · Boutique
A distinctive downtown stay near West Street dining and the arts district, offering a convenient base for the U.S. Naval Academy and historic sightseeing. Check the walking route and parking charges.
Graduate by Hilton Annapolis
West Street / Arts District
Boutique · City
A collection of historic accommodations around State Circle, appealing to travelers who prioritize period character and easy access to Maryland State House and historic streets. Room layouts vary among buildings.
Historic Inns of Annapolis
State Circle / Historic District
Boutique · City
An upscale hotel on Westgate Circle, convenient for the Annapolis Arts District and visitors who prefer a modern hotel base near, rather than directly on, the harbor. Check the distance to City Dock.
The Westin Annapolis
West Street / Park Place
City
A hotel along West Street offering a practical base for downtown restaurants and local sightseeing. Compare rates and parking with waterfront hotels before reserving.
Hilton Garden Inn Annapolis Downtown
West Street / Downtown
Value · City
A full-service downtown hotel a short walk from City Dock and the Naval Academy.
Loews Annapolis Hotel
Downtown
City · Family
A stylish, good-value hotel with a rooftop bar on West Street.
Hotel Annapolis, Tapestry Collection by Hilton
West Street / Downtown
Value · City
A friendly downtown hotel close to restaurants and the historic district.
O'Callaghan Annapolis Hotel
West Street / Downtown
City · Value
A small inn in historic houses near the Naval Academy gates.
Gibson's Lodgings
Historic District
Boutique · Value
A waterfront resort across the Bay Bridge with a beach and spa.
Chesapeake Bay Beach Club
Stevensville / Kent Island
Beach
Curated Accommodations
WHERE TO STAY
November in Annapolis
High 56°F · Low 40°F · Rain 3.3 in
Museums and performances become good options as days shorten. Explore historic harbor walks, naval history and Chesapeake cruises. Seasonal highlight: United States Naval Academy Commissioning Week generally in May. Planning note: boat schedules and waterfront festival calendars.
April–June and September–October. Check the forecast and local opening schedules before committing to outdoor excursions.
Best Times to Visit Annapolis
WHEN TO GO
06
Regional Transfers
Annapolis is reached primarily by road from Baltimore or Washington-area airports. Prearrange airport pickup if needed.
05
Water Taxis and Harbor Cruises
Seasonal water services operate around the harbor. Check routes and schedules before relying on a water crossing.
04
Walking the Historic District
Main Street, the harbor and nearby landmarks are best explored on foot, though some brick sidewalks are uneven.
03
Downtown Parking
The historic waterfront has narrow streets and limited parking. Use established garages and confirm any city shuttle service.
02
Getting Around Locally
The downtown waterfront is walkable, but parking is limited; use garages and local shuttles.
01
Arriving by Air
Baltimore/Washington International Airport is a convenient air gateway.
Baltimore/Washington International Airport is a convenient air gateway. The downtown waterfront is walkable, but parking is limited; use garages and local shuttles.
Getting Around Annapolis
GETTING AROUND
KEEP EXPLORING
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