- Top Attractions
- See & Do
- Eat & Drink
- Hotels
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- Vacation Rentals
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Why Visit Annapolis
Annapolis's colonial street plan, laid out in 1695, centers on State Circle and Church Circle. The Maryland State House, where the Treaty of Paris was ratified, is one of the top attractions in Annapolis and a prime example of Georgian architecture.
Experience the Chesapeake Bay's vast shoreline. Sailing is integral here, with popular Wednesday Night Races from April to September. While visiting Annapolis, you can also kayak Ego Alley or stroll the scenic waterfront U.S. Naval Academy grounds.
No Annapolis travel guide is complete without mentioning Chesapeake blue crabs. Locals insist on no-filler crab cakes and steamed crabs with Old Bay. Don't miss the creamy crab soup or fresh oysters, often enjoyed at historic taverns by the water.
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Quick Travel Essentials
- Apr-Jun & Sep-Octmild weather, fewer crowds
- Jul-Aughot and tourist-heavy
- Wintercool, chance of snow
- #ComfortableShoes
- #LightClothing
- #RainJacket
- #Sunglasses
- #ReusableWaterBottle
- 3-4 days for highlights
- 5-6 with side trips or beaches
- USD ($)
- English
- English is an official language here
- #U.S.NavalAcademy
- #AnnapolisHistoricDistrict
- #MarylandStateHouse
- #CityDock
- #BannekerDouglassMuseum
- #St.Mary'sChurch
- Sail on the Chesapeake Bay
- Explore the local seafood scene
- Visit the Naval Academy Museum
- Stroll through historic streets
- Attend a sailing regatta
Recommended Hotels in Annapolis by Experience
Things to do in Annapolis
Discover
Exploring Annapolis reveals a city rich in history, from the U.S. Naval Academy's historic campus to the iconic dome of the Maryland State House. Discover colonial architecture at the William Paca House & Garden and maritime heritage at the City Dock.
Experience
Sail the Chesapeake Bay, a classic local pastime, or take a guided walking tour through the historic district. Enjoy seasonal events like the U.S. Sailboat Show, catch a performance at Maryland Hall, or browse local goods at a weekend market.
U.S. Naval Academy
Historic campus for U.S. Navy and Marine Corps officers.
Maryland State House
Oldest U.S. state capitol in continuous legislative use.
William Paca House & Garden
18th-century Georgian mansion with a restored colonial garden.
Annapolis City Dock
Bustling waterfront hub for boating, shopping, and views.
Annapolis Maritime Museum
Museum showcasing the city's oyster and boat-building past.
Schooner Woodwind Sailing Cruise
Classic sailing experience on the Chesapeake Bay.
Quiet Waters Park
Sprawling park with trails, gardens, and water access.
Before You Arrive
Getting There
Fly into Baltimore/Washington Int'l Airport (BWI), 20 miles away. An Annapolis shuttle bus or rideshare from the airport to city center takes ~30 min. For a train to Annapolis, take Amtrak to New Carrollton Station and arrange a taxi for the final leg.
Getting Around
The historic district is highly walkable. Annapolis GO provides bus routes for public transport in Annapolis, connecting neighborhoods. For a scenic perspective, use the water taxi. The free Circulator trolley is excellent for getting around downtown.
Local Essentials
Driving in Annapolis presents challenges with its narrow colonial streets and limited parking. If using a car rental in Annapolis, pre-book garage space. Wear comfortable shoes for the cobblestones. Many attractions are conveniently close for walkers.
Where to Stay in Annapolis
Where to Eat and Drink
Celebrate
To truly explore Annapolis, you must eat its traditional food. Taste iconic steamed blue crabs and rich crab cakes. The local custom is waterfront dining, enjoying fresh seafood with harbor views. This is the heart of the city's flavor.
Enjoy
For the best restaurants in Annapolis, start at Boatyard Bar & Grill's nautical scene, weekend brunch. Grab a drink at the historic Middleton Tavern, request patio. Taste the buzz at Miss Shirley's Cafe for brunch, arrive early.
Boatyard Bar & Grill
Famous for its vibrant atmosphere and fresh seafood.
Chart House
Upscale dining with stunning waterfront views.
Osteria 177
Fine Italian dining with a romantic, upscale vibe.
Mike's Restaurant & Crab House
Classic waterfront spot to eat steamed crabs.
Events & Festivals
Celebrate
Explore Annapolis's heritage through must-see events. Maryland Day in March offers $1 entry to historic sites like the William Paca House. The Fourth of July features a parade and fireworks over the harbor, celebrating the nation's birth.
Enjoy
Discover contemporary Annapolis cultural activities. The acclaimed Annapolis Film Festival showcases narrative and documentary films each March. Enjoy indie and bluegrass at music festivals or classical concerts by candlelight.
Maryland Day Celebration
March weekend with $1 access to museums and historic sites.
Annapolis Film Festival
March event screening over 70 independent films with panels.
First Sunday Arts Festival
Outdoor art market with live music, May through November.
Annapolis 4th of July
Downtown parade followed by a fireworks display over the harbor.
Kunta Kinte Heritage Festival
September celebration of African diaspora culture and arts.
Annapolis Boat Shows
October in-water shows for sailboats and powerboats.
Military Bowl Parade
December parade with Clydesdales before the football game.
A beautiful, walkable city
Annapolis is such a great place to just walk around. The old brick streets and colonial buildings are everywhere. It's compact, so you can see a lot without a car, which was perfect. Felt very historic and well-preserved.
Impressive piece of history
Spent a good amount of time exploring the US Naval Academy campus. The scale of it and the history you feel just by walking the grounds is really something. It gives the whole city a very distinguished quality.
All about the water
Annapolis really lives up to its reputation as a sailing town. The number of boats at the City Dock is amazing. The whole place is oriented toward the water, giving it a unique feel compared to other historic cities.
Loved the historic downtown
Walking down Main Street was a highlight. The little shops are great and the old architecture is fantastic. We found a great spot for some crab cakes that was just perfect. It's a really pleasant place to spend an afternoon.
Cozy and historic feel
The area around the State Circle is so picturesque, especially on a chilly day. The whole city has a quiet, dignified feel. It was nice to walk around and then pop into a pub to warm up. Very comfortable and easygoing.
Great food, great views
The scenery by the water is beautiful, even in winter. But the food really adds to it. The Maryland crab cakes I had were incredible, and being able to eat that kind of fresh seafood while looking out at the bay is a top-tier experience.