10 Things to Do in Annapolis

Since 1845, the Academy has been educating the officers of the United States Navy, and the Academy campus is steeped in that history and culture. Highlights include the United States Naval Academy Museum and the beautiful domed chapel that holds the ornate crypt of John Paul Jones, father of the U.S. Navy. The Blue Angels—the U.S. Navy’s famous fighter jet demonstration team performs a fly-over and airshow at every graduation.

Since opening its doors on Main Street in 1965, Chick & Ruth’s Delly has been a favorite for midshipmen, governors, locals and tourists alike—it’s an Annapolis institution. Come early to enjoy a hearty breakfast and take part in the daily Pledge of Allegiance, recited every morning –it’s a Chick & Ruth’s tradition (8:30 AM on weekdays, 9:30 AM on weekends).

If you’ve got a boat to show off, cruise to Ego Alley, a narrow waterway in the heart of historic downtown Annapolis. Once you arrive, or if you’re just there to watch, stop in for a bite and a classic rum cocktail at Pusser's Caribbean Grill. With dockside seating right on Ego Alley, it’s prime real estate for taking in the yachts. 

Sailors come from all over the world to experience the largest and oldest in-water sailboat show on Earth. The Annapolis Dock becomes a showplace for the most beautiful and exotic boats in the world, and they’re worth seeing whether you’re shopping or just dreaming.

Touring these halls is like taking a walk through history. Older than the country itself, the Maryland State House was built in 1772 and is the oldest state house still in use. Once the capital of the nation, it was here that the Treaty of Paris was signed to end the Revolutionary War, and General George Washington resigned from his post as commander of the Continental Army. 

More than 100 yachts gather every week from late April through August for the famous Wednesday Night Races, and there's no better spot for race night than the decks of schooners Woodwind and Woodwind II. The two boats put passengers to work as they compete in a class all their own. Since this regular event happens in the "Sailing Capital of the World," the vessels are fast and the competition is fierce, and the Woodwind crews keep you in the thick of the race and up to speed on the action! With your help, your boat might even win the race!

Go a bit off the beaten path to enjoy some of the best crabs and Maryland seafood around. Built over the water with a gorgeous view of quiet Mill Creek, Cantler's is a can’t-miss! Check out the live tubs out back—they’re often full of crabs and fish fresh off the boats.  Or check out the entire area's selection at our Annapolis and surrounding area Crab & Oyster Trail.

Watermark offers so many ways to immerses visitors in the history, culture, and fun of Annapolis, both by land and by water. History comes alive when you stroll through the charming streets of Annapolis with a colonial attired guide on any one of Watermark's fascinating walking tours. Or explore the Chesapeake Bay from Annapolis on an unforgettable journey on a  Watermark cruise or yacht charter. Be sure to take advantage of the Annapolis Water Taxi for touring the Annapolis Harbor.

The official African-American history museum of Maryland focuses on two celebrated figures in American history: Frederick Douglass, the great writer and abolitionist, and Benjamin Banneker, the 18^th-century mathematician, astronomer and author whose work inspired many in the drive for freedom.

Rams Head is one of the best venues in the country to see national touring musicians across all genres. The intimate space keeps the audience close to performers so you never have to miss a note. There’s an extensive bar, and the in-show wait staff delivers the pub’s fantastic food and beer right to your table.