Set sail on the Chesapeake Bay on a Watermark Journey. Spend a full day on the bay exploring Annapolis and Baltimore Harbors and all the history they hold. Learn about the region’s African American history, cruise to and from the Key Bridge, or tour the banks of the U.S. Naval Academy. 

Watermark also offers a land-to-sea experience, where you can explore downtown Annapolis both by boat and foot. 

More than 100,000 people from all over the world flock to the halls of the U.S. Naval Academy Museum to immerse themselves in the history of the Navy. Within two floors of Preble Hall, you’ll find exhibits dedicated to the history of seapower, the creation of the U.S. Navy, and the role of officers who graduate from the U.S. Naval Academy and go on to lead sailors in places near and far. 

Admission is always free, and the museum is open every day of the week, so you can get your Naval history fix no matter when you visit.

Annapolis comes to life in the Annapolis Collection Gallery, where not only the art but also the building are steeped in centuries of history. In 1865, the Slama family built the gallery building and opened a shoe store on the main level. Nearly 150 years later, Katherine Burke moved her gallery into the space, which features priceless black and white photographs of historic Annapolis and six renowned Annapolis masters. 

Peruse oil paint, watercolor, and mixed medium artworks alongside vivid black and white photos of Charles Emery, Aubrey Bodine and Marion Warren. Burke plays Chopin throughout the gallery so you can sink into the spirit of the classics as you immerse yourself in old Annapolis.

Find a happier and healthier you at RASA Juice Shop, which features colorful, freshly-pressed juices. Vibrant bottles line the shelves in their Annapolis storefront, offering a burst of flavors like cacao mint, beet, and green juice. Beyond the bottles, RASA also stocks earth-friendly beauty and locally-made home goods to help you feel refreshed inside and out. 

Purchase RASA’s full roster of juices on their online shop so you can get your fresh fix in between visits to Annapolis. They even offer juice reboot boxes to keep you at your best.

Food and fun are on the menu at Rams Head Tavern, as is ice-cold beer fresh from the tap. This casual tavern is a go-to for nights on the town or casual pub grub, like the dynamite burger or grilled PB&J for lunch and the mac and cheese or bison meatloaf for dinner. Belly up to a table in the cozy dining room with exposed brick walls and dark wood paneling, exactly as a tavern should be. 

At Rams Head, kids eat free every Wednesday, and happy hour specials are available every day of the week from 3 p.m. to 7 p.m., so you can swing by the tavern even if it’s just for a drink and a snack.

Located in the heart of downtown Annapolis, Dock Street Bar and Grill serves up seafood and cold beer with a special focus on the vibe. Owner Mike Wroten believes that the place makes the beer since beer tastes the same no matter where you are. Their blue brick storefront gives way to exposed brick walls and wooden tables, the perfect setting for digging into crab cakes or sipping a beer while catching a game. 

Their crab cakes are a local favorite but don’t miss the Maryland crab soup, tuna tartare, or even a lobster salad sandwich with a hearty helping of curly fries.

For more than 50 years, Chick & Ruth’s Delly has been an Annapolis go-to for great food every meal of the day. You’ll find something for everyone on Chick & Ruth’s menu, which includes everything from crab omelets and benedicts for breakfast and Navy subs and surf and turf for dinner. Don’t skip dessert, as all breads and pies are fresh-baked at Chick & Ruth’s. 

Though the food is reason enough to visit, Chick & Ruth’s is also full of fun traditions: they’ve been reciting the Pledge of Allegiance at 8:30 a.m. on weekdays and 9:30 a.m. on weekends since 1989.

Step into the 1760s at the William Paca House, a five-part mansion built by Paca himself. Paca was one of Maryland’s four signers of the Declaration of Independence and Maryland’s third governor, making this a priceless part of Maryland state history. Following a 1965 restoration by Historic Annapolis, the William Paca House is regarded as one of the nation’s best 18th-century homes, as well as being a National Historic Landmark. 

Meander through the home, soaking up rooms designed exactly as they would’ve been in 1760, then tour the two-acre garden teeming with native and heirloom plants.