Must-Do Additions For Your Annapolis Visit
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Must-Do Additions For Your Annapolis Visit

Getaway Staff

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.


01 Go sailing

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

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.


02 Visit the Naval Academy

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

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.


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

Maryland State House traveler1116 / Getty Images

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.


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 House & Garden Yginger Lee / Shutterstock

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.


07 Head to Sandy Point State Park

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

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.


08 Eat crab cakes

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

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.


09 Watch the sailboats

Sailboats in Annapolis Sean Pavone / Getty Images

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.


10 Drive Around Maryland

The Bay Bridge in Annapolis MikeBagley64 / Getty Images

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.


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