The Getaway
Must-Do Additions For Your Annapolis Visit

Located less than an hour away from both Washington and Baltimore, Annapolis is one of the most overlooked state capitals in the country. But this would be a mistake, as Annapolis is full of fun activities for the whole family.

Whether you're taking a day trip from one of the nearby bigger cities or you're looking to spend a few days, great seafood, easy access to the Chesapeake Bay, and lots of history make Annapolis an excellent inclusion in your vacation plans.

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01 Go sailing

Did you know that Annapolis is considered the sailing capital of the United States? With Boston right on the Atlantic Ocean and Providence surrounded by the Providence River, it's is the only state capital that sits on open water without being right on the ocean. Instead, it's located on Chesapeake Bay, which means incredible waters for recreational sailing.

If you come in October, you can see the U.S. Sailboat Show, but a summer visit means you can get on a boat yourself and enjoy some beautiful views of the bay. If you're an experienced sailor and have a day to explore, you can even sail from Annapolis to Baltimore — the journey takes between five and seven hours.

man standing on his sailing boat looking at distance Westend61 / Getty Images

02 Visit the Naval Academy

Its location right on Chesapeake Bay makes Annapolis the ideal spot for the United States Navy to train its future admirals. Touring the campus and visiting its domed chapel is a truly unique experience, especially for the history buffs in your family.

The Naval Academy has existed in Annapolis since 1845, and whether you're there for a sporting event, a chance to see the crypt of John Paul Jones, or the flyover that happens at graduation, you'll get unmatched history and culture from the moment you step on campus.

Chapel at United States Naval Academy, Annapolis Joseph Sohm / Shutterstock

03 Enjoy a shake at Chick and Ruth's Delly

Whether it's deli sandwiches, crab cakes, or their famous milkshakes, you can't come to Annapolis without making a visit to Chick and Ruth's Delly at least once. Opened in 1965, this is as iconic as it gets for foodies in Annapolis, both for quality and portion size.

If you think you've got the stomach to take down a six-pound milkshake, you can win a free T-shirt by successfully completing the challenge. Even without the challenge, you need to have at least one meal here before you leave Annapolis.

04 Explore the Maryland State House

This building was the People's House when Annapolis briefly served as the national capital at the end of the Revolutionary War. It's the oldest state house that's still in use today, as it dates back to 1779 and still hosts the Maryland General Assembly.

Touring it is easy, as it's open to the public 363 days a year, closing only for Christmas and New Year's Day. There's also some architectural history mixed in among the legislative narrative: it's home to the oldest wooden dome in the United States, constructed in 1794.

Maryland State House traveler1116 / Getty Images

05 Visit the Banneker-Douglass Museum

Annapolis' Banneker-Douglass Museum is just across the Chesapeake Bay from Talbot County, the birthplace of Frederick Douglass, one of the first free African-Americans in the era of slavery. The museum is home to Maryland's collection of African-American history, dating back to the first slaves arriving in 1633.

Today, it celebrates the efforts of Black individuals to change Maryland for the better, such as Thurgood Marshall's work in modernizing Maryland's educational system and Harriet Tubman's Underground Railroad. The excursion is an excellent way to learn about the past and gain an appreciation for African-American contributions to modern culture!

06 Visit William Paca's House and Gardens

William Paca signed the Declaration of Independence, and his home from the 1760s has been restored to its colonial style and preserved as a monument to the past. Today, it boasts some of the most beautiful gardens in Annapolis, as well as authentic architecture and decor from the colonial period. Whether you prefer to take a step into the past or marvel at more than two acres of gorgeous landscaping, William Paca's House and Gardens is sure to delight.

William Paca House & Garden Yginger Lee / Shutterstock

07 Head to Sandy Point State Park

If you'd like to visit the beach without driving out to Maryland's Eastern Shore (about 100 miles from Annapolis), Sandy Point State Park is an excellent choice. The beach only stretches for about a mile, but you will see some of the best sunsets that Maryland has to offer while dipping your toes into the waters of the Chesapeake Bay.

If you're into bird watching, this is also one of the state's best places to do it.

The red sandy beach of Sandy Point State Park near Annapolis Shackleford Photography / Shutterstock

08 Eat crab cakes

Chesapeake Bay produces some of the best crab cakes you will ever eat, so make sure to bring an appetite. There's nothing like fresh Maryland crab, and if you really want to enjoy them like the locals, make sure to have plenty of Old Bay seasoning on hand.

Whether it's cakes, dip, or steamed crab, Maryland really loves its crustaceans, and after one taste, you're sure to fall in love too.

Crab cake with lemon and vegetable on the side bhofack2 / Getty Images

09 Watch the sailboats

Walking the City Dock is one of the most pleasant ways to pass the time in Annapolis; you're surrounded by sea air, comfortable temperatures, plenty of shops and restaurants, and the boats sailing in and out of Chesapeake Bay.

If you're looking for a leisurely day to do as you please, strolling, sightseeing, and shopping along City Dock is a great way to relax in a gorgeous setting.

Sailboats in Annapolis Sean Pavone / Getty Images

10 Drive Around Maryland

The Old Line State is a beautiful place to explore, and Annapolis is a short jaunt to a lot of great destinations. Whether you want to visit Washington, Baltimore, the Eastern Shore, or head on up to Delaware, you're never more than two hours away from where your plans might take you.

Making Annapolis your home base for a driving trip around Maryland means that you get the best of both worlds. The result? An unforgettable getaway.

The Bay Bridge in Annapolis MikeBagley64 / Getty Images

11 Book a tasting at Great Frogs Winery

Nestled on the outskirts of Annapolis, Great Frogs Winery offers a tranquil escape into the world of winemaking. Visitors are invited to indulge in a tasting experience that showcases the vineyard's array of exquisite wines, from bold reds to refreshing whites. The serene setting, coupled with the opportunity to learn about the winemaking process from the passionate vintners, makes for an unforgettable afternoon. Don't miss out on pairing your selections with locally sourced cheeses and charcuterie for the full experience.

12 Try a flight at Forward Brewing

Forward Brewing, a gem tucked away in the Eastport neighborhood, is redefining the craft beer scene in Annapolis. This cozy nanobrewery offers an ever-changing lineup of craft beers, each brewed with a unique twist. Opt for a flight to sample a range of their creations, from hoppy IPAs to smooth stouts, and pair your picks with delicious, locally sourced bites. The laid-back atmosphere and friendly staff make Forward Brewing a must-visit for beer enthusiasts and casual drinkers alike.

13 Visit the Museum of Historic Annapolis

Step into the past at the Museum of Historic Annapolis, where the city's storied history comes to life. Located just a stone's throw from the bustling City Dock, this museum offers a deep dive into the people, places, and events that have shaped Annapolis. Through a variety of exhibits, visitors can explore everything from the colonial era to the present day, gaining insight into the city's significant role in American history. It's an essential stop for anyone looking to understand the rich tapestry of Annapolis's past.

14 Join a Watermark Cruise

Embark on a Watermark Cruise for a picturesque journey through the waters of Annapolis. These narrated tours offer a unique vantage point of the city's historic landmarks, the Naval Academy, and stunning waterfront homes, all from the comfort of a spacious boat. Whether you're soaking up the sun on a daytime adventure or basking in the glow of a sunset cruise, you'll discover why Annapolis is famed for its maritime heritage. It's the perfect blend of relaxation, education, and scenic beauty.

15 Have afternoon tea at Reynolds Tavern

Reynolds Tavern isn't just a dining destination; it's a step back in time. Offering a traditional English afternoon tea, this historic tavern serves up a delightful array of teas, scones, sandwiches, and pastries in an 18th-century setting. The elegant dining rooms and charming garden provide the perfect backdrop for a leisurely afternoon. Whether you're celebrating a special occasion or simply looking for a unique culinary experience, afternoon tea at Reynolds Tavern is a refined pause in the heart of Annapolis.

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