Things to Do in Annapolis, Maryland: A Perfect Day Trip from DC or Baltimore
Planning a day trip to Annapolis, Maryland? Explore the Naval Academy, historic downtown, waterfront views, boat tours, Chick & Ruth’s Delly, and Quiet Waters Park.
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If you’re looking for a charming waterfront destination packed with history, great food, and beautiful views of the Chesapeake Bay, Annapolis, Maryland is hard to beat.
The city might be small, but it’s packed with personality. As the capital of Maryland and home to the United States Naval Academy, Annapolis blends colonial history, maritime culture, and lively waterfront energy in a way that few towns on the East Coast can match.
Most visitors only need one day in Annapolis to experience the highlights. Spend the morning exploring the Naval Academy, wander through the historic downtown streets in the afternoon, grab lunch at a legendary local deli, and finish the day by the water or at a nearby park.
Here are some of the best things to do in Annapolis if you’re planning a day trip.
Visit the United States Naval Academy
One of the most interesting places in Annapolis — and the reason many visitors come in the first place — is the United States Naval Academy.
Founded in 1845, the Naval Academy trains future officers for the U.S. Navy and Marine Corps. Even if you’re not particularly interested in military history, the campus itself is worth visiting. It sits right on the water and feels more like a historic university than a military base.
Visitors can explore parts of the grounds, but there are a couple of ways to experience it.
Guided Naval Academy Tours
Guided tours are available through the visitor center and are a great option if you want deeper context about the academy’s history, traditions, and buildings.
A guide will walk you through highlights such as:
• Bancroft Hall (the largest dormitory in the world)
• The Chapel and John Paul Jones Crypt
• Tecumseh Court
• The beautiful waterfront views of the Severn River
Tours usually last about an hour and are well worth the time if you’re curious about academy life.
Self-Guided Visit
If you prefer exploring at your own pace, you can also walk around parts of the campus independently after checking in at the Naval Academy Visitor Center.
The visitor center itself is surprisingly interesting. Exhibits explain what midshipmen go through during their four years at the academy, including the famous Plebe Summer training.
Even if you only spend an hour here, it’s one of the most unique experiences in Annapolis.
Walk the Annapolis Waterfront
One of the simple pleasures of visiting Annapolis is just walking along the harbor.
The downtown waterfront area near City Dock is full of sailboats, small marinas, and historic brick streets. It’s the kind of place where you’ll want to slow down, grab an ice cream, and just watch boats move in and out of the harbor.
The views across the water are classic Chesapeake Bay scenery — sailboats drifting by, historic buildings lining the shore, and the occasional tall ship or naval vessel.
You’ll also see several monuments and public art installations along the waterfront that reflect Annapolis’s long maritime history.
It’s a beautiful spot for photos and a great place to take a break between sightseeing stops.
Related: If you’re exploring the Mid-Atlantic region, another fantastic outdoor destination is Great Falls Park, where the Potomac River crashes through dramatic rock formations just outside Washington, DC.
Explore Downtown Annapolis
One of my favorite parts of Annapolis is the historic downtown area.
The streets are lined with colorful colonial buildings, small boutiques, cafés, and locally owned shops. Many of these buildings date back to the 1700s and 1800s, so walking around downtown feels a bit like stepping back in time.
You’ll find:
• souvenir shops
• nautical-themed stores
• local art galleries
• bookstores and gift shops
• cafés and bakeries
Main Street and the surrounding side streets are especially fun to explore.
Even if you don’t plan to shop much, this area is perfect for just wandering around for an hour or two.
Related: Annapolis sits roughly halfway between Washington DC and Baltimore’s Inner Harbor, making it an easy and scenic day trip from either city.
Eat at Chick & Ruth’s Delly
No visit to Annapolis feels complete without stopping at Chick & Ruth’s Delly.
This legendary diner has been serving enormous breakfasts and classic deli meals since the 1960s. It’s famous for its over-the-top menu, quirky atmosphere, and huge portions.
Some of the most popular menu items include:
• crab cake platters
• stacked deli sandwiches
• breakfast plates that could feed two people
• milkshakes and desserts
The deli is also known for its patriotic traditions. Many mornings the entire restaurant participates in a group recitation of the Pledge of Allegiance, which is surprisingly fun to experience.
Even if you’re not especially hungry, it’s worth stopping in for a milkshake or a slice of pie.
Take a Boat Tour of the Harbor
Because Annapolis sits right on the Chesapeake Bay, getting out on the water is one of the best ways to experience the city.
Several companies offer boat tours around Annapolis Harbor and the Severn River. These tours typically last about an hour and give you a completely different perspective of the city.
Depending on the tour you choose, you might see:
• the Naval Academy from the water
• historic sailing ships
• waterfront mansions
• Chesapeake Bay scenery
If you enjoy maritime history or sailing culture, this is one of the most relaxing activities you can add to your Annapolis itinerary.
Visit Quiet Waters Park
If you want a break from the busy downtown area, head just a few minutes outside the city center to Quiet Waters Park.
This beautiful park sits along the South River and is one of the nicest outdoor spaces in the Annapolis area.
The park features:
• scenic walking trails
• waterfront views
• open grassy spaces
• picnic areas
• a small playground for kids
One of the prettiest spots in the park is a gazebo overlooking the water. It’s a peaceful place to sit for a few minutes and take in the Chesapeake Bay scenery.
Quiet Waters Park also hosts seasonal events and art displays throughout the year.
If you’re visiting Annapolis with kids, this is a great place to let them run around after exploring downtown.
Stroll the Historic Streets
Beyond the waterfront and Main Street, Annapolis has one of the best preserved historic districts in the United States.
Many streets still follow their original colonial layout, and the architecture reflects centuries of maritime and political history.
As you wander through town, keep an eye out for:
• colonial townhouses
• historic inns
• old churches
• hidden courtyards
Annapolis was once one of the most important ports in the early United States, and that legacy still shows in the city’s architecture and street layout.
Even if you don’t have a specific destination in mind, walking around these neighborhoods is one of the most enjoyable things to do in Annapolis.
Tour the Maryland State House
Right in the middle of historic Annapolis you’ll find one of the city’s most important landmarks: the Maryland State House.
This isn’t just any capitol building. The Maryland State House is actually the oldest state capitol still in continuous legislative use in the United States. Construction began in 1772, and the building has been part of American history ever since.
For a short period after the Revolutionary War, Annapolis even served as the temporary capital of the United States, and Congress met in this very building. It was here that George Washington famously resigned his commission as commander-in-chief of the Continental Army in 1783, one of the most significant moments in early American democracy.
Visitors can walk through much of the building on a self-guided tour. Inside you’ll find historic legislative chambers, exhibits about Maryland history, and plenty of architectural details that reflect the building’s colonial origins.
Even if you only spend 20–30 minutes here, it’s one of the most historically important places to visit in Annapolis.
Related: Maryland may be small, but it offers a surprising range of destinations — from the waterfront charm of Annapolis to the mountain scenery around Deep Creek Lake.
Visit the Banneker-Douglas-Tubman Museum
Another meaningful stop in Annapolis is the Banneker-Douglas-Tubman Museum, which focuses on the history and cultural contributions of African Americans in Maryland.
The museum is named for three remarkable figures connected to the state:
• Benjamin Banneker, a mathematician, astronomer, and surveyor who helped map Washington, D.C.
• Frederick Douglass, the famous abolitionist and writer who escaped slavery in Maryland
• Harriet Tubman, the Underground Railroad conductor who led dozens of enslaved people to freedom
Inside the museum you’ll find exhibits covering centuries of African American history in Maryland — from slavery and the Underground Railroad to civil rights and modern culture.
The museum is smaller than many large city museums, but the exhibits are thoughtfully curated and powerful. It’s a meaningful place to learn more about an important part of Maryland’s history that often doesn’t get as much attention as it should.
Tour the William Paca House and Garden
One of the hidden gems in downtown Annapolis is the William Paca House and Garden.
William Paca was one of the signers of the Declaration of Independence and later served as governor of Maryland. His restored Georgian mansion sits right in the historic district and offers a fascinating look at life in the 1700s.
The house itself is beautifully preserved, but the real highlight for many visitors is the two-acre colonial garden behind the property.
The garden is designed in a traditional 18th-century style and includes:
• brick pathways
• ornamental flower beds
• terraces overlooking a small pond
• quiet shaded benches
It’s surprisingly peaceful considering how close it is to the busy downtown streets. If you enjoy historic homes or simply want a quiet place to wander for a bit, the William Paca House and Garden is definitely worth visiting.
Related: If you’re planning a longer Maryland trip, many visitors pair a visit to Annapolis with time on the coast in Ocean City, Maryland.
Why Annapolis Makes a Great Day Trip
One of the best things about Annapolis is how easy it is to visit.
The city sits roughly halfway between Washington DC and Baltimore, making it a perfect day trip from either city.
You can easily spend:
• the morning at the Naval Academy
• the afternoon exploring downtown
• lunch at Chick & Ruth’s
• the evening watching boats on the harbor
It’s the kind of place that feels relaxed and historic at the same time — a refreshing change from the pace of larger nearby cities.
Final Thoughts on Visiting Annapolis
Annapolis might not be a huge city, but it’s packed with charm, history, and waterfront scenery.
Between the Naval Academy, historic downtown streets, great restaurants, boat tours, and parks like Quiet Waters, there’s more than enough here to fill a full day.
Whether you’re interested in American history, Chesapeake Bay culture, or just want a relaxing waterfront stroll, Annapolis is one of the best day trips in Maryland.
If you’re already exploring the Mid-Atlantic region, it’s absolutely worth adding to your list.
