If you are looking for a waterfront destination that combines history, charm, beautiful scenery, and dockside restaurants, look no further than Annapolis, Maryland. The capital of Maryland is located on the Chesapeake Bay. Come enjoy its vibrant culture and historic architecture.
Maryland State House is the oldest state capitol still in continuous legislative use. It briefly served as the U.S. Capitol after the Revolutionary War. This is where George Washington resigned his military commission.
Here are 15 of the best things to do in Annapolis (from a local’s perspective) that will make your visit unforgettable.
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Stop at the Visitors Center
Start your visit at the Annapolis Visitor Center, where the staff can help you plan your itinerary with maps, attraction recommendations, walking tour information, and dining suggestions. They’ll also provide insider tips for making the most of your time in Maryland’s historic capital.
Be sure to browse the gift shop for locally made souvenirs and pick up brochures highlighting the city’s museums, historic homes, and waterfront attractions.
Stroll Around City Dock and Ego Alley
The heart of Annapolis is City Dock. Watch boats sail through the narrow waterway known as Ego Alley. You’ll find colorful historic buildings, outdoor cafes, and plenty of photo opportunities.
I love to sit on a bench and watch the residents on their boats. Sometimes the occupants include a dog. Canines are often as curious about me as I am about their novel home on the water.
Explore the Historic District
Take a leisurely stroll through the historic district and admire the beautiful architecture of the 18th-century buildings in Annapolis.
“Visit iconic landmarks, step inside historic homes, wander through a colonial garden, and explore over 400 years of the diverse history of Annapolis.”—Historic Annapolis, Inc.
Historic Annapolis, Inc., a nonprofit preservation and history organization, was instrumental in securing the Colonial Annapolis Historic District’s listing on the National Register of Historic Places.
Visit the U.S. Naval Academy
The United States Naval Academy is based in Annapolis. Take a guided tour of the campus and visit the Naval Academy Museum, which features exhibits on naval history and the academy’s role in shaping the country’s military leaders.
Stroll around the campus, as there is a lot to explore. Explore the Commodore John Barry Memorial, the beautiful chapel, the crypt of Paul John Jones, and the historic naval exhibits. Bancroft Hall is one of the world’s largest dormitories. You should allow 1.5 to 2 hours for your tour.
Book a Boat Trip
Annapolis is known as America’s Sailing Capital. A one-hour harbor cruise provides excellent views of the harbor, Naval Academy, and Chesapeake Bay. Step aboard the classic Harbor Queen for a narrated cruise of Annapolis Harbor and the banks of the U.S. Naval Academy.
I have even taken my dog on the 40-minute Annapolis Harbor Cruise run by Watermark Journey. The cost is $25 (adult). The dog is free! After you get off the boat, wander along the Chesapeake Bay harbor. Sniff the salty air. Sit on a bench and gaze out on the Chesapeake Bay. Watch the ducks bobbing on the water.
Walk Maryland Avenue and Main Street
Annapolis is a shopaholic’s dream. You will suddenly find yourself desperately yearning for a sailor’s shirt or hat. I love to meander down Main Street and peer in the shop windows. If you arrive early on a weekend morning, you won’t have to fight the crowds.
These charming streets are lined with colonial buildings, boutiques, galleries, and cafes. They offer some of the best architecture in the city and are perfect for leisurely exploring.
Visit the Old Fox Bookstore & Cafe
The next stop should be the Old Fox Books & Coffeehouse on Maryland Avenue. Their slogan is “Where story lives.” You can’t miss this building with its striped blue awning, red cafe tables and chairs, and fox mascot. The staff displays books outside so customers can browse.
Housed in a historic downtown building, Old Fox Books & Coffeehouse is a cozy stop where you can browse carefully curated books, enjoy a cup of coffee, and soak up the welcoming atmosphere of historic Annapolis.
Book a Walking Tour
My favorite part about visiting Annapolis was wandering the city streets, looking at houses, and pondering life four centuries ago. If you want to learn more about Annapolis’ history as the capital of the United States, consider a two-hour walking tour.
“You will pass middling homes and gentry mansions on your way to explore the Maryland State House.”-Watermark Journey
Period-costumed guides bring the city’s colonial history to life with engaging stories and local insights.
Explore Historic Houses
Annapolis is the perfect city to explore if you love Georgian architecture. Three examples of Palladian-style homes in the city are the William Paca House, the Hammond-Harwood House, and the Chase-Lloyd House.
Hammond-Harwood House
Step inside the Hammond-Harwood House to admire one of America’s finest examples of Georgian architecture, featuring elegant period furnishings and an outstanding collection of decorative arts.
William Paca House
Tour the beautifully restored William Paca House, an 18th-century Georgian mansion with period rooms and a stunning two-acre terraced garden once owned by a signer of the Declaration of Independence.
Chase-Lloyd House
Admire the stately Chase-Lloyd House from the street, a magnificent Georgian mansion built in 1769 and considered one of the finest historic homes in Annapolis.
Visit the Annapolis Maritime Museum
Learn about the city’s rich maritime history at the Annapolis Maritime Museum & Park. The museum features exhibits on oysters, boatbuilding, and the ecology of the Chesapeake Bay.
“The Annapolis Maritime Museum & Park (AMM) educates youth and adults about the Annapolis area’s rich maritime heritage and the ecology of the Chesapeake Bay through programs, exhibits, and community events.”
Find Street Art
Go on a street art scavenger hunt. Annapolis has murals hidden on the sides of brick buildings, painted on rooftops, and clustered in a parking lot. Learn about the city’s history by studying these local artists’ work.
I particularly love the street art featuring cats and dogs. The mural is located near the U.S. Naval Academy. I took some pictures of Parker doing dog selfies!
Don’t miss visiting the Pearl Bailey Mural. It was created in collaboration with George “Lassie” Belt and the children from the Stanton Community Center.
On this once-thriving block, places like Susie’s Tea Room, Dixie Hotel, and The Washington Hotel operated. Pearl Bailey once performed in these venues.
The striking Pearl Bailey mural honors the legendary singer’s performances in Annapolis’s historic African American Fourth Ward. It also celebrates the neighborhood’s rich cultural legacy and preserves the memory of a vibrant community lost to urban renewal.
Tour St. John’s College
While many visitors think that the Naval Academy is Annapolis’ oldest college, this distinction belongs to St. John’s College. Known as the “Great Books” college, it was founded in 1696 as King William’s School.
Visitors can roam the college green and sit in the lounge chairs. Admission is also free to the college’s Mitchell Art Museum. Spring exhibitions run from April 9 through June 5, and special events include musical performances, poetry readings, gallery talks, and more.
“St. John’s College is the third oldest college in the United States (reportedly behind Harvard, established in 1636, and College of William and Mary in 1693).”
Take a free self-guided walking tour of the historic campus of St. John’s College to explore one of America’s oldest colleges, where you’ll discover centuries of history, beautiful Georgian architecture, and landmarks including McDowell Hall and the free Mitchell Art Museum.
Visit the Banneker-Douglass-Tubman Museum
As the State of Maryland’s official museum of African American heritage, the Banneker-Douglass-Tubman Museum documents, interprets, and promotes African American history and culture (particularly in Maryland) through exhibitions, programs, and projects.
The Banneker-Douglass-Tubman Museum is operated by the Maryland Commission on African American History and Culture. Admission is free! Museum hours are Tuesday through Saturday (10:00 a.m. to 4:00 p.m.)
Tour the Maryland State House
Tour the historic Maryland State House, the oldest state capitol in continuous legislative use in the United States and the only one to have served as the nation’s capital. George Washington resigned his commission in 1783 at the Maryland State House.
Admission is free, and visitors can explore the building on a self-guided tour while admiring its impressive wooden dome, historic chambers, and exhibits.
Bring your Dog
I regularly bring my golden retriever (Parker) for weekend walks in Annapolis. The town caters to dogs, so you’ll find water bowls at the front of stores and even the promise of a treat if you visit a pet store.
Final Thoughts
Whether you’re strolling along the historic waterfront, touring centuries-old homes, browsing independent bookstores, or dining on fresh seafood, Annapolis offers the perfect blend of history, maritime charm, and small-town hospitality. With its walkable streets, colonial architecture, and welcoming atmosphere, Maryland’s capital is an ideal day trip from Washington, DC, or a relaxing weekend getaway. No matter how you spend your time, you’ll leave with a deeper appreciation for one of America’s most beautiful and historic cities.
