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Forget Baltimore: Discover the Charm of This Historic Seaport — Sailing Adventures and Colonial Architecture Await

By Jamie Gambetta · Last updated on January 12, 2026

Founded in the mid-17th century, this historic waterfront city went on to play a remarkable role in shaping the story of the United States. Its past has been exceptionally well preserved, with colonial-era buildings lining the streets—some of which witnessed events that helped change the course of history.

Set along the sparkling Chesapeake Bay in Maryland, Annapolis enjoys a beautiful coastal setting that has given rise to lush parks, yacht-filled marinas, and a wide range of outdoor activities. Beyond its museums and historic homes, visitors can soak up a lively theater and arts scene, relax by the water, or enjoy leisurely walks along the city’s scenic waterfront.

12. Hammond-Harwood House

Hammond-Harwood House

Constructed in 1774, the Hammond-Harwood house is one of several impeccably preserved colonial era buildings in Annapolis from the 18th century. What sets this one apart is its exquisite architecture, the work of the esteemed William Buckland.

The Georgian-style mansion is eye-catching inside and out. The elegant facade makes way for gilded carvings and handcrafted moldings on the first floor. As you explore the home, you’ll wander by original furniture and an art collection that includes works from Charles Willson Peale and a portrait of his daughter. In the painting she’s holding a doll, the same doll that remains on display two centuries later.

11. Annapolis Maritime Museum & Park

Annapolis Maritime MuseumPreservation Maryland / Flickr

Annapolis has a long connection to life on the water, including being the base of the United States Naval Academy. But one way to explore this connection is at the Annapolis Maritime Museum and Park.

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The museum is on the banks of Back Creek in the location of the city’s final oyster packing plant. The museum will guide you through the oyster and boat building industries, including the enormous re-creation of an oyster reef within its aquarium.

The museum will help travelers understand how the rivers, bay and ocean shaped local culture and developed Annapolis’ economy. You’ll also have a look at the fascinating Oyster Wars, waged between locals and pirates.

10. Alex Haley Memorial

Alex Haley Memorial

Along Ego Alley is the home of the Kunta Kinte-Alex Haley Memorial. In this exact location, that Kinte was brought to the United States as a part of the slave trade. He was an ancestor of Alex Haley and the major figure in his novel, Roots.

The memorial is a unique sight and the only one in the U.S. that recognizes the arrival of a specific slave. The site helps convey Haley’s desire for healing and reconciliation. It’s made up of three sections. The first is Haley reading to children. The other two are a collection of plaques, and a 14-foot gilded compass.

9. St. Anne’s Church

St. Anne's Church

Annapolis’ College Avenue cuts through the heart of the city leading up to Church Circle. This is a gorgeous roundabout with St. Anne’s Church right in the middle of it. The circle brings together many of the main streets and from the church, you’ll be right by the Banneker-Douglass Museum and the Maryland State House.

The church you see today is the third iteration and was built in 1858 in the style of the Romanesque Revival. The first church, however, was built back in 1704. It’s an episcopal church that has a soaring bell tower and elegant facade. But it’s the interior that’s the most captivating, including the stained windows and the silver communion service from the original church.

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8. Sandy Point State Park

Sandy Point State Park

On the shores of Chesapeake Bay, Sandy Point State Park is the place to be when the sun is shining. The impressive park has no shortage of fun activities. Its white sand beach leads to the refreshing waters of the bay where you can sunbathe or go for a swim under the watchful eye of the lifeguards. The beach area also features showers, restrooms, and a picnic area complete with grills.

Away from the beach, discover the park on the four miles of biking and walking trails. The forests are particularly great for bird watchers. Or head to the local marina to launch your boat and explore the bay. Fishing is also allowed on the park’s pier.

7. Banneker-Douglass Museum

Banneker-Douglass Museum

There’s no shortage of stories to hear in Annapolis, but the Banneker-Douglass Museum takes a close look at African American history in Maryland. The museum is an official curator of the state’s African American history, and has laid it all out for you, from the first slave arrival in 1633 to the modern day.

There is a range of multimedia exhibits that will take you through significant moments in the past. These include the efforts of Thurgood Marshall to affect the schooling, the famous Frederick Douglass speech, even the reward poster for Harriet Tubman. All three were Maryland residents who helped change the course of history.

6. William Paca House & Garden

William Paca House & GardenMr.TinDC / Flickr

In 1765, the finishing touches were added to a luxurious colonial home belonging to William Paca. Mr. Paca was an exceptional student, who graduated from Philadelphia College at age 18 with a Master’s degree. He would go on to become state governor and later was one of the signees of the Declaration of Independence.

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Today, the grandiose home showcases his storied life while preserving one of the best examples of colonial architecture in Annapolis. Surrounding the home are opulent terraced gardens, with a pool and summer house. Within the historic mansion, each room has been redecorated with period furniture and art. To learn even more about William Paca, head to the on-site visitor center.

5. Quiet Waters Park

Quiet Waters ParkMatthew Beziat / Flickr

On the South River, across from the majestic U.S. Naval Academy, you’ll find Quiet Waters Park. As the name suggests, it’s a great place to go for a breather and to enjoy some fresh air among nature. The large public park features six miles of walking and biking trails for those seeking exercise or a casual ride.

There are several amenities that help make your day at the park even better. Outside of the forests, you’ll have access to spacious lawns, home to picnic areas and outdoor pavilions. There’s a dog beach and park for your furry friends, along with a small marina that rents out watercraft, like kayaks.

4. United States Naval Academy

United States Naval Academy

Established in the 1840s, the United States Naval Academy is one of the leading public institutions in the country. While still a functioning academy, it’s now a National Historic Site and open to visitors.

The Naval Academy has a fascinating museum that gives you a look into the longstanding history of the navy. Admire relics and memorabilia that shed light on conflicts, victories, and life training at the Academy. A highlight is the model ship exhibit. Each model was created at the time the actual ship was in development. It becomes more impressive when you see the oldest model is from 1650.

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For an elevated experience, join a guided tour. This will take you behind the scenes, to see the Academy’s Athletic Hall of Fame (featuring Roger Staubach), the campus’ enormous dorms, the chapel, and the amazing crypt of John Paul Jones.

3. Ego Alley

Ego Alley

Much of your time in Annapolis will be focused on the city’s incredible history. But for a change of pace, make your way to Ego Alley. Otherwise known as City Dock, Ego Alley received its cheeky moniker because of the number of lavish boats within the harbor.

Annapolis runs right out into the gorgeous Chesapeake Bay and is one of America’s best day sailing destinations. For this reason, you’ll find no shortage of elaborate yachts. For a crisp morning walk with a coffee in hand or a romantic sunset stroll, wander along the boardwalk that envelopes the waterfront.

Along the way, you’ll find benches with lovely views as you watch the yachts come in and out. In the summer, grab some ice cream at Storm Bros, a local favorite. While in winter, see many of the boats lathered with Christmas lights.

2. Maryland State House

Maryland State House

Three years after the United States declared independence from Britain, the construction of the Maryland State House was complete. Despite July 4th 1776 being the celebrated date, it was within the house in 1783 that the Treaty of Paris was signed, officially ending the war.

But that isn’t the only piece of history created in the opulent red-brick mansion. It was here the George Washington resigned as Commander in Chief that same year. The state’s general assembly also congregates here, making it the only 18th century building still a part of politics and public life in the country.

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Aside from holidays, the State House is open to explore each day from 9am to 5pm. Embark on a self-guided tour through a home so important to the timeline of the U.S.

1. Annapolis Historic District

Annapolis Historic District

As both the state capital and one of the oldest cities in the country, Annapolis has no shortage of intriguing history. In fact, before the U.S. capital became Washington D.C. the center of the country was right here. As a result, Annapolis is teeming with prominent buildings and historic landmarks.

Now a designated as National Historic Landmark District, this fascinating part of Annapolis is home to many of the attractions on our list. These include the William Paca House, the Maryland State House, and the beautiful St. Anne’s Church.

The city hosts a range of guided and self-guided tours that will peel back the curtain on local history, the significance of the buildings and how they both paved the way for modern day America.

Map of Things to do in Annapolis, MD

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